Last month I found myself glaring at my closet as if it had insulted me. It had, sort of. I was venting to my friend Sarah over coffee about how nothing to wear and she pointed out that I “dress like I’m scared of standing out.” Fair critique.
White oxford, navy slacks, brown belt, dad trainers. Same hellacious casual outfit I’d worn since 2021. Exactly zero personality.
That closet glower carried over into actual mouthing because holy shit was my closet rough. Everything I owned blended into itself.
Neutral colours.
Obscene amount of jumpers. Stand-out? Hell no, I looked like I wanted to disappear.
Eventually I gave up and defaulted to my “work uniform” – dark jeans, light blue button-up, grey cardigan – and went into the office looking like every other menswearblogreading marketing professional in the Midwest who shops at J. Crew. Later that night I was bored on Reddit procrastinating work (hi, my name is Ryan and I’m a slave to the almighty procrastination thread) when I came across this discussion about small changes to your wardrobe that can have a big impact.
One dude mentioned that he swapped out his canvas trainers for leather dress shoes and was suddenly being treated more seriously at the office. Someone else posted that ever since they started wearing a simple chain bracelet they’d got twice as many dates on Tinder. Nothing outrageous or crazy difficult, but little changes that made them feel more intentional about their wardrobe.
I decided I would try this as an experiment of my own. Every day for thirty days I would upgrade one part of my outfit. Not overhaul my look – I work in marketing and wear skinny jeans as a cutting edge power move these days, so replacing my whole wardrobe would’ve had my bank account murdering me in my sleep – but one small part of my outfit that would push my wardrobe slightly beyond my comfort zone.
I texted my roommate to keep me accountable. “I’m conducting a wardrobe experiment starting tomorrow,” I said. “I realise I dress like a conformist grownup dolphin. Gonna see if changing 1 thing about my outfit each day makes me somehow more ‘individualistic.’ Will post pics.” His response: “Thank God. Thought you only owned like 3 shirts.” Gold.
Tier. Day one was embarrassingly easy. Rather than reaching for my standby beat-up leather belt from Target I threw on a really nice belt I’d purchased while sightseeing in Denver last summer and promptly never wore because it “didn’t feel like enough of a lift from my normal outfit to justify wearing it.” It was a nice brown leather with this faint grain pattern that instantly elevated my plain-Jane jeans-and-polo.
My coworker stopped me during our morning huddle to ask if I’d lost weight. When I motioned to my new belt she examined it and nodded sagely. “Hmm. Yeah man, that looks a lot better.” Baby steps.
The real game-changer came on day six. I used to think pocket squares were exclusively for men’s rights activists who read Summer as a verb, but I had this dusty blue one with tiny white polka dots that I received as a gift from my sister two Christmas’ ago. Still had the tags on it.
I bundled it up (wrinkled, obviously) and stuffed it in my blazer pocket and wowee zowee. What a difference that little square of fabric made. My blazer went from Monday morning “have an important client call” standby to “I know what I’m doing.” Got at least three compliments on it, including from our building security guard who had never before made eye-contact with me past a terse “morning.” I sent him a pic text in which he replied: WHO IS THIS PERSON By week two I was feeling pretty good about things.
Switched from my normal white button-up to this pale pink one I’d bought off-brand at Banana Republic but never wore because I was “too scared anyone would notice.” Spoiler: no one noticed. Went with some grey wool socks I’d been gifted a few Christmas’ back instead of the cotton ones I normally defaulted to. Not noticeable changes at all, but little things that made me feel like I cared about what I was wearing.
Even broke out my dad’s cufflinks one day. Nothing too crazy, just simple silver ones, but added just enough wow-factor to all my button-ups. The crazy part wasn’t really that people noticed (although they very much did) but how much my own damned attitude towards myself had changed.
Something about wearing what I considered to be my “good clothes” on a nondescript Tuesday rocked my whole demeanor. I found myself holding myself up straighter, making sure not to get coffee on my shirt, actually hanging my blazer up in my office instead of tossing it over my chair like a preemptive move for amateur dramatics. Week three is when I really started getting creative.
The low-hanging fruit were gone, so I started thinking outside the belt loop, so to speak. Borrowed my buddy Drew’s vintage Omega Speedmaster for a couple days (after he threatened to break every bone in my body if I so much as sneezed near it). I wore an Apple Watch daily, but they’re function over form and honestly about as stylish as a Casio Calculator watch.
This baby though?! Fuck. The simple black face with silver brushed steel bracelet took my whole look from baseline Slackwear to “Oops I have to run to the store for minute but this meeting will totally wait.” My boss stopped me mid-presentation to admire it. “Jacob I didn’t know you were into watches.” We spent the next five minutes discussing old school watches instead of me presenting the quarterly budget review.
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The review eventually happened (don’t tell my boss) but afterwards he invited me to this dinner next week with all these biggerwigs in our industry. Some conversation I never would have had if I hadn’t worn that watch. Failures were had, naturally.
Wore this silky Italy scarf tucked into my collar – I think I saw some InstagramModel asshole wear one and thought it looked cool? Fuck knows. Looked like I was auditioning for Broadway’s production of Hamilton.
Removed around lunchtime and pretended it never happened. Same thing with these sick-ass vintage tie clips I found at my local thrift store. Kept sliding around no matter how I adjusted it and drove me absolutely bananas.
Ended up stuffing it in my pocket so nobody would see it. Good portion of week four was spent re-learning basics I’d long neglected. Get your shoes cleaned.
For fucks sake RUN those babies by Joe’s Shoe Shine every few months. Seriously changed my entire outlook on casual outfits. Was cheap and only had them spot clean my favourite pair of loafers but took them from blah to insanely rich looking.
Started wearing this sample cologne I’d snagged from Nordstrom back in December (birthday month!) instead of just plain ol’ deodorant and holy shit did that make a difference. Not only could I smell myself throughout the day but people were suddenly inches away from my face during conversations. Even took time to get a decent haircut.
Instead of grabbing the first available stylist like I normally did told the woman about my antics last month and actually asked her for recommendations on cutting and styling. Ended up with this cool asymmetric vibe going on that I’ve been rockin’ all week. Feels vaguely narcissistic, this whole text, but I’ve definitely had a much better month since starting this experiment.
Day thirty. Always bittersweet ending a monthly challenge, amirite? But since I was going to blaze into the weekly realm anyhow I decided I’d kill two birds and really dress the part.
Slapped on my navy suit, new pocket square, polished shoes, knit tie instead of my typical smooth silk, rocked Drew’s watch like the unabashed fossil nerd I am, and even called an Uber so rainwater wouldn’t ruin my entire day. Seriously felt like I was someone else walking into our monthly all-hands meeting. Less that my appearance had drastically changed and more that feeling put-together for an entire month had altered my entire outlook on dressing nice.
Our creative director – who communicates solely through nuanced eyebrow raises and micro nods of disapproval – stopped me in the hallway to compliment my tie/pocket square combo. “Hey Jacob, I’ve noticed you’ve been dressing sharper lately. Look good.” And holy shit did that hit different when Sarah – a mutual friend of Drew who was in town for the weekend – did a full double take when I showed up. “Whattheactualfuck?” were her exact words as she looked me up and down. “Who are you and what did you do to Ryan?” Turns out my month of madness was obvious. “Dude,” she laughed when I explained my little project. “Tom is wearing his fancy watch to the basketball courts tonight so guys will think he’s a banker on weekends.” “That’s classic,” I laughed. We hugged it out and made small talk for a bit until Sarah and I were left alone waiting for our Uber’s. “You look good,” she said smiling, clearly happy for me. “I don’t know dude, it’s like you’re actually trying now.” TRYING.
As if I hadn’t been trying these past thirty days. I smiled and hugged her back. “No seriously! When I first met you, I remember thinking ‘yeah okay nnnother dude wearing a jumper.’ But now?
Holy shit. You look great man.” She shrugged. “Idk. Just keep doing you, dude.” What she said was true, though.
When I looked in the mirror that morning I barely recognised myself. I’d dressed similar throughout the entire experiment: jeans, some sort of top, jacket.
But where as day one I’d felt sloppy and unkempt, that Tuesday I felt like a million bucks.
Brand new belt, that badass watch Drew lent me, butter soft leather boots instead of my standby Nike trainers. Little changes that added up to seemi nglike I gaveafuck. Little changes.
Man, do they matter more than we think. You don’t have to go broke or reinvent yourself overnight. Just wear that good shirt instead of pulling the first thing you grab from your closet.
Throw on a nice watch. Or wear a pair of dress socks with your trainers. Small swaps that make people question your entire wardrobe.
Then smirk as they complain to their friends about how “that guy thinks he’s so fancy with his sockpants.” Challenge complete. But as I’m cleaning out my closet to return Drew’s watch and find a home for my new pocket squares I realise…I have become that guy.
