The one closet habit that screams “I’ve given up on looking good”

Okay, I need to tell you about something mortifying that happened last week. I was rushing to get dressed for a work meeting, grabbed what I thought was my decent black blazer from the closet, and didn’t really look at myself until I was in the elevator at my office building. That’s when I caught my reflection in those unforgiving elevator mirrors and realized I looked… sad. Not just tired-sad, but like I’d given up on myself sad.

The blazer was wrinkled in a way that suggested it had been wadded up in the back of my closet for months. The sleeves were slightly too short – had they always been that short? The shoulders pulled weird when I moved my arms. And there was this tiny stain near the third button that I’d apparently been ignoring for who knows how long. I looked like someone who’d grabbed random clothes in the dark and hoped for the best.

Standing in that elevator, I had this horrible realization that this wasn’t an isolated incident. This blazer wasn’t uniquely terrible – it was just part of a whole category of clothes in my closet that I’d describe as “fine, I guess.” You know what I mean. The stuff that’s not obviously unwearable but isn’t actually good either. The pieces you reach for when you can’t find anything better, then spend the whole day feeling slightly off about your appearance.

After that elevator moment of truth, I started paying attention to how often I was settling for these mediocre pieces. The black pants that gap at the waist but work with a belt. The cardigan that’s the right color but pills every time I wash it. The flats that used to be cute but now look like they’ve been through a wood chipper. All these items taking up valuable real estate in my closet while actively making me look worse.

I mentioned this revelation to my friend Sarah, who works as a stylist for people way more put-together than me. She literally laughed out loud. “Claire, you’ve discovered what I call the ‘almost’ problem. It’s the first thing I deal with when someone hires me because their closet is full but they never have anything to wear.”

Apparently this is such a common issue that every stylist has a name for it. Sarah calls them “almost” pieces. Her colleague Marcus refers to them as “compromise clothes.” Another stylist friend told me she calls them “settling pieces” and says they’re style poison – worse than having obvious fashion disasters because at least you know not to wear those.

“The problem with ‘almost’ pieces,” Sarah explained over coffee, “is that they lower your standards without you realizing it. You get used to clothes that don’t quite fit right, don’t quite look good, don’t quite make you feel confident. Then that becomes normal, and you forget what it feels like to put on something that actually works.”

This hit way too close to home. I thought about all those mornings when I’d try on three or four different outfits, none of them feeling quite right, before giving up and wearing something that was merely acceptable. How many times had I walked around all day feeling slightly uncomfortable in my own skin because nothing fit properly?

The more I thought about it, the more I realized my closet was basically a graveyard of fashion compromises. The dress I bought because it was on sale, not because I loved it. The jeans that are almost the right size but not quite. The sweater that’s a little too big but was expensive so I keep wearing it anyway. The shoes that look okay but hurt my feet after an hour.

Each of these items represents a moment when I settled for less than what I actually wanted. And collectively, they were making me look and feel like someone who’d given up on looking good.

Sarah suggested I try an experiment: go through my closet and identify everything that falls into the “almost” category. Not the stuff I obviously never wear – that’s easy to get rid of. The insidious pieces that I do wear but never feel great in. The clothes that make me feel like I’m wearing a costume that doesn’t quite fit.

The results were honestly depressing. I filled two garbage bags with items that technically functioned as clothing but weren’t doing me any favors. Pants that were the wrong length. Tops that pulled across the chest. Dresses that looked cute on the hanger but made me feel frumpy when I wore them. A whole drawer of bras that had lost their elasticity but somehow stayed in my rotation.

But here’s the thing that surprised me – getting rid of all that mediocre stuff didn’t make me feel like I had nothing to wear. It made getting dressed easier. When every option left in my closet actually fits and looks decent, choosing an outfit becomes way less stressful. Who knew?

I realized I’d been approaching my wardrobe all wrong. Instead of buying things I absolutely loved, I’d been accumulating stuff that was “good enough.” Instead of investing in pieces that made me feel confident, I’d been settling for whatever was convenient or cheap or available in my size at the time.

The “good enough” mentality is everywhere in how we think about clothes. We keep the black pants that sort of fit because we need black pants for work. We hold onto the white t-shirt that’s slightly see-through because white t-shirts are wardrobe staples. We wear the uncomfortable shoes because they match everything. But what’s the point of having “everything” if none of it makes you look or feel good?

I started thinking about this like dating. You wouldn’t stay in a relationship with someone who was merely tolerable, right? Someone who checked the basic boxes but didn’t actually make you happy? So why was I filling my closet with clothes that I merely tolerated instead of pieces that actually worked for my body and lifestyle?

The hardest category to purge was what I think of as “expensive mistakes.” The designer dress I bought on sale but never felt comfortable in. The leather jacket that cost a fortune but never looked right on me. The handbag I saved up for but hardly ever carry. There’s this weird psychology around expensive clothes where you feel like you have to keep them because they cost so much, even when they’re clearly not working.

But Sarah had a good point about this: “An expensive mistake is still a mistake. That designer piece you never reach for isn’t serving you any better than a cheap piece you never reach for. Actually, it’s worse because it’s taking up mental space too – every time you see it, you’re reminded of the money you wasted.”

That hit hard, but she was right. I had several expensive pieces that I’d kept out of guilt rather than because I actually wanted to wear them. Getting rid of them felt like admitting I’d made bad choices, but keeping them wasn’t undoing those choices – it was just making them ongoing sources of closet stress.

Another category that was surprisingly hard to let go of was what I call “aspirational pieces.” Clothes I bought for the person I thought I might become rather than the person I actually am. The cocktail dress for parties I never get invited to. The hiking boots for outdoor adventures that happen mostly in my imagination. The blazer that made me feel like a serious business person but was totally wrong for my actual casual office environment.

These aspirational pieces aren’t inherently bad, but they were taking up space and creating this weird guilt every time I saw them. Like my closet was constantly reminding me of all the ways I wasn’t living up to my own expectations. Getting rid of them felt like giving myself permission to dress for my actual life instead of some fantasy version of it.

The category that really surprised me was basics. I’d always thought of basics as foolproof – how wrong can you go with a white t-shirt or black pants? Turns out, very wrong. I had accumulated so many “basic” pieces that were just okay instead of holding out for ones that were actually good. The white t-shirts that were slightly see-through. The black pants that didn’t quite fit right. The bras that had seen better days but were still technically functional.

Sarah pointed out that basics are actually the most important things to get right because you wear them constantly. “If your foundation pieces don’t fit well and make you feel good, everything you layer on top is compromised,” she said. “It’s like building a house on a shaky foundation – nothing’s going to work properly.”

After my big purge, I had to resist the urge to immediately replace everything I’d gotten rid of. Sarah advised me to live with the gaps for a while, to figure out what I actually missed versus what I thought I should miss. This was surprisingly revealing. There were categories I thought were essential that I didn’t miss at all, and other gaps that became immediately obvious.

The process made me realize how much mental energy I’d been wasting on clothes that weren’t quite right. All those mornings spent trying on multiple options because nothing felt good. All that time spent adjusting and readjusting pieces that didn’t fit properly. All those days of feeling slightly uncomfortable in my own skin because my clothes weren’t working with my body.

Now when I shop, I have completely different standards. Instead of asking “Is this cute?” or “Is this a good deal?” I ask “Will this make me feel confident and comfortable?” and “Do I love this enough that I’d be excited to wear it?” It’s a much higher bar, which means I buy way less stuff but everything I do buy actually earns its place in my closet.

My friend Emma came over last week and immediately noticed the change. “Your closet looks so much more… intentional,” she said, which I took as a huge compliment. Everything left in there has passed the test of being something I actually want to wear, not just something I’m willing to tolerate.

I think the “almost” problem is so common because we’re taught to think of clothes as necessities rather than choices. Like we need to have a certain number of items in certain categories, regardless of whether those specific items actually work for us. But having a closet full of clothes you don’t really like is worse than having fewer clothes you actually love.

The other day I was getting dressed for work and realized I was looking forward to putting on my outfit instead of dreading it. Every piece I tried on actually fit properly and made me feel good. It sounds so basic, but it was genuinely a revelation after years of settling for “good enough.”

I’m not saying you need to throw out your entire wardrobe and start over – that’s not realistic for most people’s budgets or lifestyles. But I am saying it’s worth being honest about which pieces in your closet are actually serving you versus which ones you’re just tolerating. Those “almost” pieces that never quite feel right? They’re not doing you any favors, and getting rid of them might be the best thing you can do for your style.

Life’s too short to spend your mornings feeling bad about how you look because you’re wearing clothes that don’t quite work. And definitely too short to have elevator mirror moments that make you question all your life choices. Sometimes the most stylish thing you can do is subtraction, not addition.