Cleaning & Organizing

I Finally Organized My Closet—Here’s What I’m Ditching vs. Keeping


Fun fact about me: I’ve moved 10 times (soon to be 11) in the past nine years. No part of me loves moving… no matter how many times I settle into a new space, I just can’t seem to get the moving process down to a perfect science. To say that it’s one of my least favorite activities is an understatement. But, if there’s one positive to packing up once a year and relocating, it’s having the forced opportunity to come face-to-face with my clothing of “add to carts” past, sort out what I want to keep, donate, or sell, and facepalm myself for not wearing the one item I swore I would get use of upon purchasing.

I wouldn’t necessarily describe myself as a hoarder but I will admit that I have plenty of faults when it comes to accumulating pieces in my wardrobe. First being that I am a sucker for a good sale. The limit to the number of times I’ve bought an item for the markdown alone simply does not exist. When I see a red sticker price, I become blind to reality and will overlook what otherwise would be a wardrobe deal breaker for me (i.e., a far-too-large and non-refundable floral dress from Madewell that mocks me every time I sift through my closet). 

My second fault is holding on to pieces that “might be useful for a costume party.” Oh yes, ladies. I’m talking mesh, sequins, sparkles, and the whole nine yards. And to absolutely no ones’ surprise, these items sit in the back of my wardrobe, take up prime real estate, and wait longingly for the chance to be loved again. 

And last but not least, I am a creature of habit. I prefer neutrals over color, opt for comfort, and return to my foolproof outfit combinations time and time again. But every so often, I think, “I should step out of my comfort zone.” That’s when I’ll buy something pink (gasp!), purchase a trendy item that “looked really good on that one IG influencer,” or invest in something I saw our fashion editor rock in the office pre-COVID. While there’s nothing “wrong” with the pieces I add in my feeble attempt to be cooler than I actually am, they simply don’t get as much love as the other pieces in my wardrobe.

Four hours, two dramatic “I cannot go on” breaks, and a couple of sweat droplets later, I accumulated four garbage bags of clothes to donate, sell, and toss depending on their condition. In an effort to live a more minimalist life (and make room for new pieces, of course), here are the items I’m ditching and the ones I’m holding on to for dear life this season:






Ditching: Right idea, wrong fit

When the blazer trend came back with a vengeance, I ran to my local H&M and eagerly walked to checkout with three of them draped over my arm. Unfortunately, I missed the mark on these guys in the size department. I bought each to fit like a glove and I’ve learned after a few seasons of styling that I prefer a larger, oversized fit. I’ve added some mediums to my collection which I’m super happy with but, now, my fitted blazers don’t get a lot of attention. 

Same goes for this plaid, sherpa-lined jacket that I loved when I bought it. I don’t know if I’ve shrunk it over the years or if I’ve just “grown,” but no matter how cute it is, I simply won’t wear it. Feeling like the Michelin Man when I squeeze into it/having limited mobility of my arms is not the move. 


Ditching: Mesh

This one doesn’t need much of an explanation. There was a short period of time in college where the trendy girls wore mesh tops/bodysuits with a black bra underneath. I could never work up the courage to actually wear them and, looking back, I am elated that that is the case. Regardless, I’ve been holding on to them for the off chance that I can use them in some kind of costume setting but I’ve firmly decided that if a costume calls for mesh, it’s not the costume for me! If mesh ever decides to rear its head and come back into style (the only shock left of 2020), I’ll reevaluate at that time.


Ditching: The quarter-zip that’s seen better days

Alright, I’m not going to lie… this one hurt. This Patagonia sweater has been with me through many trials and tribulations of life. It’s soaked up tears born from a bad breakup, been wine-stained during iconic pizza nights with my pals, and been washed with darks and denim galore in many unforgiving community laundry situations. Given the fact that this sweater was a beautiful shade of ivory at one point in time, I would deem it to be one of the most worn, sad-looking articles of clothing I’ve ever known. I think I’ve only worn it twice in the past year so I think it’s an appropriate time to part ways. Thank you for your service, you will be missed.


Ditching: The “it was on sale” Madewell dress

I bought this floral Madewell dress at their end-of-summer sale and there were three things that doomed this purchase from the start: 1) I didn’t need it (I have an impressive amount of floral dresses), 2) I didn’t really even want it, and 3) it was a final sale item. I know how careless that sounds… but a Madewell dress for $25? I couldn’t pass it up. To my demise, it didn’t fit me right and was non-refundable. Classic.


Ditching: The trendy splurge item I never wore

When visiting New York City one summer, I found myself in a trendy, overpriced boutique and was talked into this jacket by one of the sales associates. If I told you how much it was, you would probably spit the contents of whatever you’re sipping on all over your computer screen. The price of this jacket was so absurd but, for some reason, that did not stop me from being persuaded that I needed it. The jacket itself is fine, it’s just not my style. I kept promising myself that I would incorporate it into some outfit formula, but in the four years I had it, I just couldn’t seem to pull it off.


Ditching: The first-time interview clothing that’s so not me

OK, to be honest, I never liked any of these items from the start. When the time came for post-grad interviews, I needed a ‘fit to impress my potential employers. I walked cluelessly into Ann Taylor at my local mall and let one of the associates dress me (and by that, I mean that I sold my soul to the Devil). I abandoned my personal style to fit a cookie-cutter look of what I thought was a “professional investment” and honestly, I haven’t looked at them since my first interview in 2016. If I need to interview again at any point, I’ll pick up options that can be dressed down and incorporated into my everyday wardrobe.


Ditching: The “out of my comfort zone” color I swore I’d wear but didn’t

I’d say that, in life, I have a good sense of who I am as a person… that is until I find myself adding non-neutrals to my shopping cart. I don’t know what it is, but I’ll just never be a “pink” person. But does that stop me from thinking“wow, Jess looks gorg in blush pink, I should give it a try,” and attempting to swerve out of my comfort zone? Of course not! I’ve found that I can still experiment with other colors (burnt oranges, deep blues, and olive greens) without looking in the mirror and feeling like I’m staring at a complete stranger.


Ditching: Non-versatile graphic tees

Don’t get it twisted, I love a good graphic tee. But when I say graphic tee, I mean the ones that are oversized, can be tucked in with mom jeans, dressed up with a blazer, and made edgy with a leather jacket. I’m looking disdainfully at you, I-would-die-for-John-B. long sleeve (pictured below). If it didn’t pass the versatile vibe check, I didn’t keep it.


Ditching: Unforgiving jeans

I just simply don’t need the negativity of unforgiving jeans in my life. It is my personal opinion that all jeans should have a bit of stretch. Over the past few years, I’ve gained some weight (pandemic stress eating didn’t help my situation, it is what it is) and while most of my jeans still button, this pair is stubborn as hell. If a pair of jeans can’t handle me post-gnocchi at my favorite Italian restaurant, they don’t deserve me at my best. Bye, Felicia.


Keeping: Oversized blazers

If I haven’t yet made myself clear, I am obsessed with oversized blazers and I get so much use out of them. I have two right now (black and plaid) and they’re not going anywhere anytime soon. They’ve been the perfect solution to Chicago’s “it’s not cold now but it will be later tonight” woes, will be great for styling business casual outfits we return to office life, and are super trendy with a graphic tee and hoop earrings. 


Keeping: Loungewear that I’ve worn at least once in the last three months

I’ve accumulated a lot of loungewear over this past year and I am not mad about it. Staying home during the pandemic has shifted my wardrobe priorities and, right now, my cozy clothes are getting a ton of attention. I’m sure there’ll be a day where I’ll have to sort through and edit out some of my comfy pieces, but thankfully, today is not that day.


Keeping: Jackets for layering

Disclaimer: Last year, I had so many bulky jackets that I had no choice but to downsize. At that time, I kept one of each jacket (leather, denim, faux fur, trench, shearling, etc.), so I truly didn’t need to do much organizing in that department this year. Nonetheless, I still did a once-over to see if anything could be sacrificed, but gleefully decided I was happy with my collection as is. 


Keeping: Chunky knit sweaters

OK, don’t come for me, but I truly believe there is no such thing as too many sweaters, especially when you live in a climate that threatens sub-zero temps in the wintertime. I kept all of my sweaters with the exception of those that were uncomfortable (yes, they exist) and/or didn’t fit well.


Keeping: Maxi/midi skirts

I’ve said it once and I’ll say it again: Midi and maxi skirts have changed my life. I’m already phasing them out for this fall (I had a few good runs with a chunky knit sweatshirt + long skirt + sneaker combo) but I am so looking forward to their return when the temps rise again.