October 16, 2026
Pro Tip: The Question to Ask When Cleaning Out Your Closet
This is a new Cup of Jo column, Pro Tips, where we ask people for their life hacks and everyday recommendations.
“A professional organizer once gave me this advice, and I’ve never forgotten it: When you’re uncertain about a dress/shirt/pair of jeans, ask yourself if you would want to run into your ex while wearing it. As soon as I heard that, I knew exactly which pieces I was ready to give away, like a denim dress that always makes me feel frumpy.” — Laura Fenton, who has lived in small New York City apartments for over 20 years
Thoughts? How do you edit your closet? Please share any tips below!
P.S. More pro tips and the #1 thing my capsule wardrobe taught me.
(Illustration by Brooke Barker for Cup of Jo.)
Tags: pro tip
Comments
163 commentsI think the best thing I ever did for my closet is find a consignment store that I like. Finding a wonderful little store that both takes my better cast-offs and has clothes I want to shop has turned my closet into a fun catch-and-release program. Because the barrier, for me, wasn’t what rubric would help me cull my wardrobe – whether Alison’s “3 words” or “seeing your ex” – but where could those clothes go that were wrong for me but still had value. It was the guilt of just giving away clothes I spent so much on that prevented me from editing them. Once I knew I was getting value for the clothes that had any value left, it was much easier to let them go. I still have too many clothes, but I have a habit now of culling every spring and fall and the delight of hearing “You have $150 in credit” when I’m buying a perfect new-to-me sweater.
I am a personal stylist and I start each client journey with a questionnaire to find out their individual style goals before we edit the closet. One helpful question to consider is, what 3 words would you use to describe your style? (these may be aspirational) Then we use those words as the lens through which we assess each item. ie Does this pleather mini skirt serve your current style goal of “classy”? If not, we donate or sell that piece. It helps remove some of the unnecessary emotion out of clothing and we can be much more productively critical.
Allison Bornstein is that you?:)
My favorite tip is from my sister: would you be excited to open this — in its current condition — as a birthday present?
Love this one!!!
Oooooooooh yes
A) If I ran into an ex, I’d probably try to hide (no matter how I looked at the time)- way too awkward! B) I’ve gotten into consignment & thrifting & I love it! If I make a mistake or my taste (or size) changes, I sell it & use the proceeds to replace it. The extra effort prevents impulse buying or collecting extra clothing.
So interesting to see the mix of responses! I laughed and it immediately made me feel some kind of way. I want to feel comfortable, confident, and unbothered when I see an ex, which is how I want to feel in my clothes. Doesn’t matter what they think of my style, since it’s changed since I’ve dated them, or whether I’m attractive to them, since my understanding of my worth has also changed since then. But I want to feel good about myself, and not all my clothes do that.
“I ask myself: ‘If I was shopping today, would I buy this?’ Works every time!
More power out there to all y’all who give no fucks about dressing to impress anyone, but even if that ex (partner, colleague, rival, etc.) is from decades ago, I would still like them to see me and go “daaaaaamn” in a good way, not “glad I dodged that bullet” because I am for sure judging them in that way! Call me shallow, but hey, I’m human and have my faults!
Exactly how I read the advicr
I think a lot of it may also have to do with your age or stage in life. I mean, I’m a 51-year-old who has been married since I was 27. I don’t even care what what husband thinks of my clothes, let alone my exes. But I did have a stylish boyfriend in my 20s who always hated my clothes and would go through my closet to try to convince me to change, and I didn’t care then, either, so maybe it’s just my personality.
Oof. No, this post instantly made me wince in a way I have never felt with CoJ’s posts. IDGAF what my exes would think of my clothing choices… if it repels them then well good! Not a litmus test I’d ever give to a wardrobe cull, more like does it make ME feel good/ have I worn it in over a year etc I know you were trying for a ‘new’ angle on this but this rubbed me the wrong way.
If I’m trying to decide, if my first feeling when I grab it is “it’s uncomfortable” (fabric/fit) it has to go- I deserve comfort with my cuteness! My friend hosts a clothing exchange once or twice a year. We bring a bag of clothes we’re sick off (like, our best stuff to donate), sort into piles, have appetizers and drinks, and go home with a bag of free new cute clothes! I have found some of my favorite things at those.
I feel incredibly lucky to be part of a friend group that is consistently overdressed and slightly wacky. I dress for the weird girls :)
This piece really inspired some interesting discourse! While I can’t say there’s an ex I still want the approval of, I thought of an old friend who ended things before I was ready. I’d almost be more inclined to choose things that don’t feel as considered if I knew I’d see them! Of course there theme for the exercise doesn’t matter – it’s whatever helps the closet-owner keep things in check. I’ve known people for whom “stuff” has been a major issue. Most of us will never fall into that camp, but it feels good to be mindful. Thank you for this prompt!
I love this idea for the column!!
Right now my wardrobe is overflowing with clothes but I wear only about 20% of them. Having just had a baby (3 months old now!) I find myself totally lost in terms of clothing. I have maternity clothing that I need to store just in case another child came along. Then there are pre pregnancy clothes that seem like they will never fit my body again but I can’t sell/donate because that would mean admitting I’ll never be that size again. My current wardrobe is high waisted Mom jeans and comfy joggers with baggy t shirts I can nurse in, I’ve never felt like such a slob and would hate to run into anyone I know, let alone an Ex!
I totally understand your dilema! I’m about to birth my fourth child, and who knows if I’ll actually fit into my pre pregnancy clothes in a few months… after my third child, we had a big move, and I brought along all of my favorite pre pregnancy clothes with the hope/expectation I’d fit into them again… 3 years later, I had to admit I wouldn’t, and no matter how cute the clothes were, it was time to let them go. I ended up giving them to a good friend and every time I see her wearing them, it makes me so happy! She looks great in them! And as the same friend once pointed out to me, it just means I get to buy new clothes! (Finances depending).
I recognise this but give yourself some (a lot) of grace. Keep those pre-pregnancy clothes in your closet (some will fit again,some won’t and many will fit but will feel wrong because your size might the same but the shape might be different). But also go out and buy a few items that make you feel beautiful and powerful in this postpartum stage.
2.5 months postpartum and I feel this deeply!!!
When I was postpartum I would wear earrings when I wanted to feel “like myself” / put together. I also found it helpful to put away everything that didn’t fit — it left me with a small wardrobe, but to me that felt better than looking at a closet full of clothes that didn’t fit
Nuuly is the best for postpartum!!! You can get sized up jeans, cute breastfeeding friendly dresses, and even some fun statement sassy things like a coat in a crazy pattern. Totally helped me find my style post baby number 2 as well as enjoy getting dressed for the first time since before pregnant.
And if the pre-pregnancy clothes never fit right again, that is OK! Your body has changed tremendously and will keep changing. My daughter is 5 now and in the past year I am finally feeling like myself style-wise again. It took a while! And the pre-baby clothes never fit me again. So I donated them. And it’s fine! Honestly, I think my style now is MUCH better than it was before I had my daughter.
This advice has a 2000s rom com feel to it, and not in a bad way! Are there really people who want to run into their ex, former boss, person who made them feel small, etc. wearing stained old sweatpants and a sweater with holes in it? Sometimes I tidy my house trying to see it through the eyes of a new friend coming over, as I can get a little clutter blind. Does that mean I am too concerned with what other people think and any friend worth having doesn’t care that there is a half of a banana on the back of the toilet seat? Sometimes I think the collective frustration of “these trying times” spills over on folks who are SO not part of the problem.
Such a soft lovely way of saying this! I agree whole-heartedly.
Very good way of thinking about this. I agree, thanks for sharing.
I knew there was going to be a lot of pushback in the comments before I even read them! For those of you among us who have never fantasized about running into an ex and leaving them at least a little wistful are more evolved than I will ever be! But the spirit of the question remains: Is this something I look and feel my best in?
Whatever works, works. I tend to hang on to old clothing for house cleaning and yard work, and whoa that can really get out of hand. Does anyone else have an overabundance of bum around/ chore clothes? How many old t-shirts do I really need? Now I have made a 1-in-2-out deal with myself for the next few months: for every item I decide to buy, I will get release 2 existing items. I will reevaluate down the line to see if I need to tweak my system. Or maybe get a new system if it’s a total fail.
Could the laundry cycle be the limit instead of a fixed number? Set aside enough for the messy jobs you do between washes, plus a spare, and choose the shirts you actually reach for. If plenty remain, that’s the separate pile to reassess. One-in-two-out controls what comes in; a chore-clothes limit addresses the stash already there.
I use old T-shirts to line the bottom of my plant pots. To keep the dirt from washing out so easily. I just cut them into squares according to the pot size. We live sort of on a ranchette so I also use them to line our cat shelters outside. Otherwise,I’ll be going to Goodwill to buy somebody else’s old T-shirts for the same purpose.
As long as I’m wearing running shoes so I can make a quick getaway, I’m good! ;-)
Haha, best fashion advice ever. =) Thanks for making me giggle. =)
Love this tip! What a great idea to cut out the emotional ambiguity that comes with whether to move on from clothing (why is this so fraught??) Looking forward to more of these (as I mourn the loss of Grace’s comics!)
I am terrible for hanging on to clothes I don’t wear. I have this thought that… maybe I’ll need it for something… or maybe wait till it comes back in style or…or…” I have been married for 30 years so, while I am not worried about exes, I understand and appreciate the sentiment of the advice: create a simple and practical question for myself to help me empty an overfilled closet. Thanks for the idea!
My college ex shamed me for wearing anything remotely sexy (for context we met at Bible school). I was so brain washed I started asking for his modesty stamp of approval on my outfits. Thank glob that relationship ended. You better believe it felt good to run into him at the beach a few months later, wearing an incredible strapless bikini. Call me toxic, but I hope that image of me is burnt into his precious mind forever!
Ok, Jez, I see you! There’s a lot of talk of revenge dresses, but nothing seems quite as effective as a bikini. I wonder what Glob would think of his inner dialogue in that moment.
Fuck yeah, Jezebel!
Goddess
We probably know each other IRL :) it took me years to wear leggings as pants. And a two piece swimsuit.
I’m in the camp who read this as meaning: do I feel good and confident and like myself while wearing it….to me, the “running into an ex” is a specific metaphor for the type of unexpected social situation that can churn up vulnerabilities. Instead of seeing it as a metaphor, some
(I hit post too soon!) Instead of seeing it as a metaphor, some are reading it literally….for those literal minded folks just “imagine if you’re wearing the clothes in a vulnerable social situation.” And for those who still think “pssh who cares what I’d be wearing in that moment,” consider yourself lucky!
Yes, this is how I see this tip. And I actually lived this after my ex-husband left for his gf (more than a decade ago now). I’d run into them sometimes, so when I left the house, I asked myself how I would feel if I ran into him/them. It worked well. Now I realize that I just wanted to feel good and confident and like I was projecting my good version of myself. A while back, I saw “What would your hero self wear?” and I liked that a lot too as a way to figure out where to take my style.
This feels like a “good for you — not for me” bit of advice. But certainly not a pro tip.
Solid advice. I have a list of ppl I keep in mind. Role models, mentors, the new girl friends of old boyfriends. But yeah I wouldn’t care what any of them thought of me but I do care how I feel about myself in the interaction. It’s weird to me that this was taken as a male gaze thing because your favorite outfit could very well be female gaze to the max. My fav looks are very Carrie Bradshaw and boys never get it. But a pink tulle coat and smile would be a win for me.
I can understand where people are coming from with the negative takes about this post but it feels like I’ve noticed a growing trend in the comments section of negativity if something doesn’t fit someone’s exact life situation even for the most lighthearded seeming posts (ie the introduction of Casey’s column). I guess this isn’t new for the internet in general but the insecurities everyone is feeling are really starting to play out more in the Cup of Jo comments section and I don’t know if that’s just the nature of a growing audience or truly exacerbated by the socio-economic climate we are in. I always appreciate how graciously the CoJ team takes feedback but there also seem to be a lot more bad-faith takes. Anyway, this is just my long winded way of saying I know it’s hard out there friends AND the internet is becoming an increasingly less pleasant place to be day by day and thank you CoJ team for all of the work you put into this space.
Hear hear!
Well said Meg!
This. Not everyone’s normal is exactly like your normal, good readers.
Maybe there are phases with this? One year loads of people were upset about the gift guide titles which felt unbelievably random to me. I wonder which year that was and what was going on in the world? Maybe an election year? Someone should write a sociology masters thesis on world events and trends of negativity in otherwise positive comment sections, please internet! I would read it! And the data would be very easy to come by :)
Complete agree! Lighten up folks and broaden your mindset. Assume positive intent. If you have nothing positive to say (or constructive), maybe keep it to yourself
Completely agree. I’m so exhausted by everyone having to be outraged by everything. (There are plenty of things genuinely worthy of outrage… not this.)
Agreed. This is literally a lighthearted post for the weekend. Please calm down. I also wonder how people can be so bothered by something on a free blog. This isn’t required reading. If you don’t like it, just leave. Do we really need to post about how you dislike it?
Thank you, Meg! How unpleasant to be “bristled” by every little thing. Maybe it’s the current state of things that has us all in porcupine mode but this fun blog is a happy respite! (No offense to cute porcupines, honest.)
I would absolutely love to read that these, Ana! Yes someone please do this!
I’m actually not dressing for an ex but for the apocalypse. My main question is, “when the apocalypse hits, will this piece let me survive it comfortably and see me until the end of my life?”
Love this perspective!
Haha
I love this!
Hahaha! This is an interesting take and it kinda goes along with me saying last night that I take some style inspiration from the Farscape character Aeryn Sun’s wardrobe.
When considering whether it stays or goes, I ask myself if I love it or if I have another similar item (say a chambray shirt) that I love more. Whatever item I love more stays, the other goes for resale/thrifting. If I love something but don’t wear it often I keep it bc I love it.
I’m the same! In my lifetime of loving clothes, I’ve only bought an item in multiple colorways twice. It’s much more fun to have variety, in my opinion. I think it keeps the numbers in check, too, since it’s not the easiest thing ever to find something that’s a) distinct) b) petite c) affordable d) in good shape or fixable and e) sourced secondhand, in my case.
If I try on a “maybe” garment and see myself slouching (or cringing, or imitating my expression at age 13, or otherwise looking uncomfortable) that’s an immediate clue to me to give it away. Of course there’s an exception for my beloved floral, all-cotton, button-front shirts with worn-out sleeves. Someday I plan to refashion these favorites into sleeveless summer tops. Fortunately I still have the closet space. Ahem.
My thing is I ask myself: have I worn this in the past year? If I haven’t: it’s on the donate/resale pile. We have a place called ‘regeneration’ near us. They are the best and they will donate what they don’t want for you. If it’s sentimental and I know I’m not going to wear it – it goes in a bin with a tag with the story on it. These are garments like my dad’s army jacket, a dress I made with my grandmother, and a poodle skirt my mom made me for Halloween.
I love that you share the story of it when you donate.
In general I kind of enjoy purging a closet but sometimes it’s tough. There are times when something is kind of special but you know you won’t ever wear it again and times when something was barely worn so you feel guilty for getting rid of it. In those times I try to think of how happy it will make someone else to get it at the thrift store. I imagine them being like ” What a cool dress” or “This looks brand new!”. I’ve had my day made at the thrift store before and I hope something I donate does the same.
I love reframing it this way. I have a skirt that I adore but it no longer fits. It brings a smile to my face imagining someone finding it and putting it to more use than I ever did.
Right? There’s a lot of talk these days about what a small percentage of donated items actually get sold. Maybe it’s vanity that makes me think my donated items can beat the odds? True thrifters donate, too!
If it isn’t roomy, then out it goes. Only 2 things I rarely wear, always stay, a sheer sleeve black blouse and a gray button front dress to wear with jeans. I will never find anything like them again.
I am often underdressed from years of work from home…. And then don’t realize it until I am at an event/party/dinner, regretting my choices in real time, all night. This is solid advice, from my perspective of perhaps too much comfort and dressing for impressing only myself!
I WFH too and I realized I was struggling with keeping too many “work clothes” around and then not focusing on my real life outfits. So I’ve transitioned to a uniform that takes minimal space (crop t shirts that look good on camera and…pants). I bought 5 shirts and rotate through them weekly. This way I can focus my spending money and effort on outside clothes I love and feel good in when I interact with people.
Ooh, Stella – as a new-WFH person, this is such a helpful idea, thank you!
This doesn’t help me! I just cannot cannot get rid of clothes. I am 53, and for example I have the miniskirt I wore when I was 18… the dress I wore when my now husband I went to a silver themed party, I just cannot…. a flatmate made me get rid of a pair of velvet knickerbockers when I was about 20, and honestly, I know I am alone in this but you have no idea how many times I have seriously wanted to wear them!
Hahah! Kirby, I am 54 and have the same problem. I occasionally manage to purge once a decade or so but still have ancient items in my closet that I can’t part with. My saving grace is I rarely buy clothes.
I know it’s not the popular wisdom, but I think it’s beautiful to hold onto those pieces of clothes that you have loved. They are a part of your story! Some people collect stamps, others collect clothes. Keep the clothes I say!
Sentimental clothing lover here, too. Because I still want to thrift new things, sometimes I sell them at vintage stores. Have you ever considered that? I’m 40, and whatever still fits I still wear! Those few things that don’t, though? I follow the shop I sell to on Instagram and hope to see shots of my pieces in their next chapter. Is it still tough? Yes. Feels necessary in my case, though!
My bestie has a Closet of Memories!! She doesn’t scrapbook/photo album and is otherwise not super sentimental but it’s so fun visiting her and seeing the dresses she used to loan me in college, at her bachelorette. Highly recommend the memory closet if you have space!!
I bet you have an incredible wardrobe, can I come over and play dress up!? But seriously, look at Iris Apfel or Dolly Parton— if you love or have a use for everything in your closet, it doesn’t matter if you have 10 things or 1000
My friend’s mom held onto her 90s wardrobe and gives her the cutest clothes every time she visits. It’s such a vibe. Hold onto your treasures, and maybe one day you can gift them to someone who will adore them.
Yeah I’m surprised by this too… I don’t want to think about my exes as I evaluate my closet even in the loosest thought exercise, they are not people who deserve even that time / judged me / didn’t appreciate important aspects of me anyways … not contorting for them for a reason. For the practical side of this, sometimes I just go for a number – getting rid of twenty things and just make myself do it. Put them in a box and see if I actually miss them.
Very much in agreement, and for similar reasons. I tend to buy clothes for things I want to do, or places i want to go. Key word being “want”. When making decisions about pieces I have to get real with myself. Did I do that? Did I go there? Am I romanticizing a life that I don’t live? I recently bit the bullet and purged tons of casual-dressy clothing. A young woman came into the sale and bought everything that was left for a new job she was starting. She was thrilled, and I felt great about moving them on to a new owner.
Yes, as for my ex-husband for example, I am still training myself to not care what I look like when I see him – I don’t have to wear makeup, I don’t have to wear “cool” clothes, I don’t need to still yearn for the attention/approval he never gave me when we were married
Made me laugh, and yes, it’s a little toxic – but sometimes I think it’s okay to be a little toxic sometimes! But my real rule for cleaning out my closet is asking myself if I would pack it for a trip. I only pack my best professional clothes for a conference; my favorite and cutest pieces on vacation. If it’s not worthy of putting in my luggage to fly across the country, then I can probably live without it. This helps me eliminate the tired, worn, or frumpy pieces that I keep holding on to out of obligation.
What a great test for what to keep! I’ll be using this tip!
Sometimes, I look in the mirror and try to not see my head. I’m just looking at the outfit and asking myself, “If I saw someone else wearing this, would I think it was a good outfit?”
I do this too! I sometimes get distracted by my messy hair or lack readiness and completely lose sight of the outfit!
Feeling a bit deflated seeing all the negative comments here, especially given that having your tip/comment of the week shared on this blog is *a big deal* lol! I totally get this perspective in terms of would I want to run into my ex wearing it- because if I ran into my ex, I’d want to feel good about myself! Not worried about what they think of me. So I think the tip is completely valid and, if it’s a case of ‘good for her, not for me’…. just let it go. No matter how self empowered, don’t care what anyone else thinks about me mindset I might be, we all get little moments and blips where we do care because we are human and messy and wonderful.
Laura, I thought this was an honest, helpful tip and I liked it! Coincidentally, I just ran into my long-ago ex at a party and you better believe that thought crossed my mind. Spoiler, I rocked it! This is a figurative exercise. Substitute ex for whatever word works for you. I am a huge proponent of not dressing for the male gaze so much so that I stopped wearing daily makeup, dying my hair, wearing high heels and tight clothing. But I’m definitely not “Yucking someone else’s yum” for this piece of advice.
Jeanne, I completely agree with you, you put more eloquently what I was trying to say! Xx
Laura, I took this literally, and now understand the point you and Jeanne were making. I apologise for the tone and language of my last sentence.
Lykke, that was so nice of you. Tone is so difficult to convey online. Your response make me smile and I needed that today
I think the underlying sentiment here is to keep things that make you feel GOOD when you wear them! Good doesn’t have to be attractive. Good can be confident or comfortable or both! It reminds me of the Marie Kondo advice to ask yourself, “does this bring me joy?” and then only buy it or keep it if the answer is yes. When I started making joy my baseline, I immediately became more selective!
I recognize this is a lighthearted tip, and acknowledge that clothes have the power to make us feel confident, cheery, united, unique, etc. Also want to share now that I’m in my 40s I dress down to make myself more approachable to my employees in recent years, so have kept some older items that my younger self would’ve tossed out ;) In my business interactions, I see folks suited up to impress or to feel confident (absolutely not a bad thing), and y’know, the actual decision-makers are dressed more casually, because they have less to prove. And yeah, people suss out your capabilities and mandates in minutes regardless your outfit of the day. So, let’s dress to feel how we want, instead of another person’s gaze. Loved my exes, but I don’t give a flying eff what they’d think of my clothes.
Love this!!
I have each seasons clothes in my main closet. I hang the hangers all going one way. When wear an item is put it back with the hanger the opposite direction. At the end of the season what I don’t wear I put in a give away box. I do this for each seasons clothes. I store those clothes one season before a give them away in case I change my mind on a item.
While I wouldn’t use this measure to edit my wardrobe I actually ran into my childhood bully yesterday after nearly 30 years and moving cities! I was actually proud she saw me with my three fabulous daughters and yes, I was relieved to be wearing an outfit I really like. The only thing I could do; stand up straight and smile!
I don’t have any exes (don’t judge; heterosexual at all girls high school/married my freshman year in college boyfriend). so I prefer to frame this in terms of my arch nemesis? nemeses? I get the whole “don’t dress for others” but like I do want to look chic/like I have my ish together when running into avowed rivals (unforch I don’t really have any because I tend to forget why I was mad at people, but I like the idea of dressing to piss off an enemy by looking like you’re thriving).
Just here to say that nobody needs to make any disclaimers for not having an ex.
I LOVE this, my kids and I joke way too much about our nemesis, nemeses, in our town. I want to look pulled together and I want my kids to be having fun in whatever they are currently doing. The “stubborn” genes are no joke.
Amen to all the ladies commenting at not caring about the male gaze. I definitely try to dresss cute as much as possible but for ME because I want to look put together. My exes thought I was great. That’s why we got together. Not because of my clothes. I am prepping for an international move and can only carry 40kg. I had stocked my closet for warm weather and thinking I’d live here a long time but now moving somewhere with proper winter and no idea how long I’ll stay! Would love tips on how to handle the clothing situation. I have winter wear but don’t want to jettison my carefully curated warm weather wardrobe.
My criteria is “Would I wear this is Paris?”. Except my ‘home clothes’, which is “Would I take my dog for a walk in this?” Doesn’t need to be expensive or trendy, but something I feel happy and comfortable in, and just gives me that good feeling…you know the one!
I know I’m being obtuse, but I have just had to allow myself to stop optimizing stuff like this. I’m happy for tips/hacks and I love when they feel like they’ll really work (like this one! I immediately thought of an ex I’d never like to see me with a hair out of place!), and this series seems really fun, so not knocking you all AT ALL, so please don’t take it that way. I think I’m just sort of over manufacturing ways I need to keep feeling bad about myself, when the list is long enough already! What are the ways we can feel good about ourselves that don’t involve more chores, basically? Can’t we just not think about the closet/laundry/childcare/dogfood/meal plan for a minute and go sit out back and look at the sunset? Sorry for the rant; I think this optimizing/perfecting conversation will always bug me on some level, because I just think you’re so wonderful exactly how you are, quantity and quality of your stuff be damned!
Yes Cyndi! I feel the same. Totally over optimising and hacking. Life is hard. We all have too much on our plates. Let’s frigging enjoy life and stop overthinking it! It’s like that Mary Oliver quote ‘what will you do with your one wild and precious life?’ – in the full poem she’s just like ‘stroll through the fields’!
For years I have asked myself, “Is this useful, beautiful, meaningful?” when editing my home and closet, but lately I have felt guided by a new question that feels like a lighthouse ~ “Would I buy this now?”
I feel like this advice seems sexist and dated. Honestly kind of shocked that this was the “debut” of this new column that was replacing the cartoons (RIP). In terms of the female readers of this blog with a past straight relationship, this advice also centers the male gaze. I should be picking out clothing based on some man’s opinion of my appearance (especially a man whose opinion I no longer value)? NO THANKS! For people in any kind of relationship, regardless of gender, the advice is that you should base how you feel about yourself and your appearance based on how someone else – not in your life – may think you look? NO THANKS, again!
it doesn’t have to mean a man, could be an ex of any gender/identity!
Yes, I know, which is why the second part of my comment said a partner of any gender identity.
If you’re trying something on in a dressing room, don’t look in the mirror as soon as it’s on—even close your eyes if that keeps you from looking. Feel the clothes on your body—does it feel good, no pinching or weird texture? The reflection can seduce us into buying something that doesn’t actually gel with walking, scooping, sitting. Also: one item in, one item out. As in, if you bring something into the closet, you have to take something out. Even if you don’t follow that rule, it’s helpful to consider.
The not looking but feeling on your body first is genius! Thank you!
I try to do this too, to think about how I feel in something before I look in the mirror. Do a quick body scan of show I feel in something first. It’s really helpful to identify a weird seam or whatever before you fall in love with the way something looks!
Been with my husband for over 20 years. I don’t think an “ex” would be able to spot me in a crowd let alone cast an opinion I cared about. Now those mean girls at a high school reunion… haha
I forget where I heard this, and maybe someone else already mentioned it, but I ask if I’d buy it again at full price. That usually gives me my answer!
Surprised to see so many comments discussing how this didn’t resonate with them. This post made me lol. Getting rid of clothing is so hard that I love how we are always on the hunt for mantras that stick to help our brains sort through our stuff.
Me too, Natalie! Also a bit surprised (and sad) at some of the negativity. Even if it’s not necessarily an ex that you picture, the scenario is helpful :) “would i feel just as good wearing this on a good day as i would on a bad day?”
Personally, the seeing-the-ex litmus test does nothing for me because idgaf what they think. My new barometer that has been so helpful if I can’t decide if I like something is “would my daughter think this was cool?”. She’s 6 and has impeccably fun taste and I hope that by taking her opinions seriously when I ask her “which shoes???” she cements in her brain that her opinions are cool even if they don’t follow the trend-du-jour.
Haha if I had asked my 6-year old, I’d have been wearing pink sparkly shoes every day (and yes actually that would indeed make me happier).
I found this a little disheartening to read. To me, it upholds the damaging social construct that our value is based on whether others might find us cute or attractive. I can understand the desire to look good when running into an ex, but I really dislike the idea of purging our closets of anything that might not show us in the most flattering light. This is another subtle signal that we should remain ever-vigilant in the goal of perpetual physical attractiveness. If I run into my ex and they think less of me because I’m not looking polished then I’ll do my best not the conflate their opinion with my self worth. I wish we all felt permission from ourselves and society to look unkempt, frumpy, and even “ugly.” P.S. The best advice I’ve ever heard about cleaning out your closet is to think about whether you would still choose to bring each article of clothing into your house if it weren’t already there. It’s so easy to keep the pants you ordered online that didn’t fit quite right, but if you were trying them on in a dressing room right now, would you still buy them? Of course, this isn’t foolproof because not everyone has the time, money, or inclination to make sure the clothes they own hit an ever-moving target of “just right.” So take this all with a grain of salt.
Really appreciate this perspective!
I understand this perspective but don’t necessarily think it needs to be read that way. I took it less as we should all want to be decked out and looking HOT to run into an ex and more as, would we be wearing something that makes us feel comfortable, confident, and at ease?
Yes yes!!
💯💯💯
Great point. Not to mention that there’s a huge glut of unwanted and discarded clothing and textiles due to fast fashion and the view that clothing can be disposed of and replaced constantly. Getting rid of a garment because you wouldn’t want to be seen by your ex in it ignores the question: where will that discarded garment end up? A landfill?
To me the question is asking how an outfit makes me feel. Vastly different. Also, to dismiss the social implications of our appearance seems like a slippery slope to just not caring anymore. It’s a huge part of life, presentation, generally because in a healthy mind it indicates *how you feel about yourself*. That’s a valuable social cue when dealing with people that I rely on according to many vectors, all of which change based on who that person is or is not in my life. Obviously I give very little, actual, thought to this process, it is mostly subconscious, but I am still aware it goes into how I navigate my interaction with that person. Unkempt stranger? Who cares? and also maybe avoid, because: issues. Unkempt loved one? Oh no! Are they ok? Do they need help or grace in some way? Or maybe just a sharp poke with a stick, lol, to help urge them into the shower?
Who cares that those losers think? They’re an ex for a reason!
I came here to say this!
Right?!
do i feel confident, comforted and like myself in those clothes (or where they an on-a-whim-buy or are they too small or do i not want to get rid of them because i think wow did i spend a lot of money on that etc.). that is my baseline. i do not wish to have my ex (even though still a lovely person) on my mind whilst going through what i want in my life NOW. confident, comforted & myself. that is how things stay in my home.
I actually like this advice because even though I don’t like the idea of dressing for other people I don’t want to run into my exes (romantic, or past bosses, co-workers, etc) in clothing that makes me feel like I can’t be comfortable or myself which cuts out a lot of clothing that I keep just because I have a limited wardrobe and so it can make me hold on to things far too long. Those moments of running into people in our past life can feel charged because we have such limited time to interact it feel like a bigger deal and like I want to be able to be in that moment and not be thinking about my clothing? (This is from someone who literally ran into an ex while wearing a giant, long sweatercoat with a waist tie/uggs with only a bra/underwear underneath. Which looked somewhat normal while we were doing the quick “hey how’s it going, hope you are happy brief chat but then having the sweater completely come open while we were mid goodbye mini hug so I was left in literally my underwear 6 inches from the fully suited-still hot but wrong for me and so glad we broke up-dude’s chest. NOT my best moment. Luckily he was kind and just laughed and retied my sweater so the entire coffeeshop line didn’t see. It was before 7am, I was just picking up a coffee at the coffeeshop next door to my hotel while I was working on a major project, this wasn’t a Bridget Jones running down the street moment! I was planning on seeing NOBODY. After that experience I do think a bit more about how to present myself in case I run into someone, that was a major “oh shit” feeling. My advice, wear underwear you wouldn’t mind your ex seeing….in a platonic way…so kidding…not the goal…but no really throw out your “bad” underwear that you don’t want even for the sweatiest or bloodiest of days as soon as you can afford it!)
Louise!! Omg!!! I am vicariously quaking.
OMG, such main character energy, LK!!! I clapped both hands to my cheeks like Kevin McCallister when I read your big reveal!
I love the underwear part of this advice. I once met someone on a plane and we hooked up but didn’t get very far because I was wearing old ratty underwear for travel. Since then, you can bet that I am travelling in the prettiest lingerie that I own. Sadly lighting has not struck again in the “meeting a hot stranger on the plane” department, but I am ever hopeful. :)
I have to say this TOTALLY resonated with me! And I’m going to use it to get rid of just a few more things. It’s so hard! I have realized that I like wearing the new things I buy, so I’ve been telling myself I have to get rid of old things if I want to buy new ones. It’s kinda working.
Hmm. I don’t personally love that filter bc it makes getting dressed all about someone else’s opinion (especially a man’s). We already spend too much time obsessing over what other people think of what we look like. Don’t mean to be a downer just sharing my thoughts! I use what I dubbed the LFC method. Love/fits/comfortable. Gotta check all 3 boxes otherwise it’s a no go (this applies for shopping and getting dressed too!) I use this constantly in my coaching practice and people love it, hopefully it resonates with some women here!
The question I’ve found helpful when buying new things or deciding what to keep is, “Would I bring this on a trip?” Obviously, not all clothes work for all destinations, but I usually pack items I feel my best in when traveling.
Oh, I love this! When I travel, I want to feel fairly chic, but the clothes also need to be comfortable and not too fussy to take care of. This one resonates for me; I’ll use it this weekend.
Oh, this is a good one. I’m laughing because I recently had to reassess my need for a particular t-shirt when I actively passed it over while packing… for a camping trip! hahaha, if it’s too old for camping, it’s probably ready to retire.
I also like the question, if I saw this in a store, would I buy it again? Even if it was Goodwill and it was only $7? Often a no! Tricky when you get into clothing exchange territory, in which case the “Have I worn this this year” tip or ex sighting tips are help!
It doesn’t resonate with me, and that’s ok! The most helpful tip is find someone to body double with while going through clothes (or anything). I have a wonderful, honest friend who does this. I’m at a place where I need to hear: “that doesn’t look good on you” or “you don’t wear it enough to keep it.”
A great tip I read many years ago – make sure all hangers are facing in one direction. Every time you return an item to the closet turn the hanger top in the opposite direction. After 6 to 9 months pull all the clothes remaining in the original direction to review what can be donated/sold.
Genius!
This series is great! Similarly, I would love if there were standing posts on CoJ where we could come at any time to comment. I’m thinking “big and small wins!” where we could share ongoing wins and celebrate one another and “I have a question” where you could ask for advice from the CoJ collective. 😊
Love these!
Pinned threads on the Substack subscriber chat?
When I clean out my closet, for casual clothes I ask myself “would I buy this again today?” No? Then out it goes to a thrift store. And for office clothes I ask myself “Do I feel like a boss in this outfit?” That faded favorite blouse and tried and true blazer with a ton of wear and tear at the shoulders have outstayed their welcome. For work clothes, before I recycle, put them on ThreadUp or donate to a local thrift shop, I check in with a local organization to ask if any women in their safe home could use work clothes in my size.
I understand this thought process, but it’s not grooving for me. What works for me is “would I buy this today?” Is it something I still need? Is it a color and style that I want to wear? I do a lot of thrifting, so it also forces me to be honest about old favorites that may have reached a condition that I’d pass on in a thrift store.
I mean it all depends on the situation, doesn’t it? I most definitely have clothes that I would prefer not to be wearing when running into an ex out on town, but would be fine for running into the ex when helping someone move, or paint the garage or pick berries in the forest 😌. I love shopping in my own wardrobe too and often let some item of clothing stew in there for a number of years and then happily reunite with it when it suddenly looks perfect combined with some newly bought/thrifted thing!
I do this too! I have been shopping my ‘set aside’ stash and it’s so rewarding to congratulate myself on a great purchase and/or be grateful I held onto it. The time and money saved is a bonus.
My pro tip is to get someone else to hold up the clothing when you’re cleaning out. Something about the physical distance lets you see it better and then you also don’t have that thing where touching it makes you want it. (https://www.sciencedaily.com/releases/2009/03/090331112723.htm) My exes are so far in my past, I could give a hoot what they would think.
I tried asking myself before I bought something if I’d want my photo taken in it, and that can work for closet clean out, too. What helps me clean out is when considering an item, if there’s even a HINT of an instant negative feeling about it then out it goes–itchy, tight, weird color, short, pilled, etc.–and no permission to say “Yes, but…” Just wave good-bye.
Love this column, can one be about socks? The sock situation in my household is a disaster. I have tried throwing out all the socks and starting over but I always end up with a sad pile of orphans and within no time, another large collection of mismatched socks. SOS!
Sam I only buy one color/type of sock for my husband and daughters. They can’t be trusted with multiple kinds of socks.
Wash them in lingerie bags.it helps especially with little people socks.
I think I heard this tip on COJ, but I now buy only one type of sock for each kid, and then I put a basket by the door, and the socks get paired and stashed in that basket. I also bought an insane amount of said matching socks for my toddler, so I’m never stressed about finding a clean pair. I don’t have any other habits like this, but it’s been truly super helpful for getting out the door!
Just stop thinking socks should match maybe?
Thanks everyone for your tips, they are all good. As an aside Kirby I once had to take my shoes off for an appointment at an embassy and explained proudly that my socks were mismatched by choice :-). I realized after I posted that part of the problem has been the rate of growth, it has been surprisingly quick recently for my teens to pass between sock size ranges, so I end up with collections of unmatchable sizes. BUT! One has finally stopped growing and the other has grown into a very large range. I honestly don’t think he can go higher – fingers crossed!
A mixed blessing in my life is that I wore a uniform from age 5 –age 40ish (Catholic school–>working in a hospital). So, I am very comfortable wearing the same thing over and over again. This makes it very easy for me to only buy things I REALLY love. If it’s pretty good…nope! I need to love it.
Respectfully, I completely disagree with this advice! For one thing, most men I’ve known have kind of limited taste in women’s fashion. For another, I simply don’t want to make any decisions based on what some dude (let alone an ex-dude) might think. My husband looks at me in horror when I wear a caftan or overalls, but you’d have to pry them from my cold dead hands.
Yeah, I don’t love framing this as a performance of beauty as worth— but if it helps people think about what makes them happy and comfortable in their own skin, hopefully it also helps them unlearn all that misogynist trash along the way?
Not all exes are men ;)
This!
It didn’t resonate with me either, that’s ok. One thing I appreciated about my ex is that he didn’t have high expectations for what I wore, and at least I was comfortably dressed while being uncomfortably married.
Same! I have some funky style and my husband’s favorite outfit on me is black t & jeans, not gonna change my look. And if I run into an ex, fine? I couldn’t care less about making them miss me or whatever
Anon, correct. I’m speaking for myself, though, and mine have all been men. Sorry if that was unclear.