Can’t even tell you how many DMs I receive on any given day from dudes asking what they should buy for some event they have coming up. Wedding. Job interview.
Birthday. First date doesn’t matter – it’s always the same premise. “Hey Keith, I’m going/wiggling to _____ and I need to look stylish. What should I buy?” On top of that they typically tack on some arbitrary budget they’re working with.
Usually $300. What kills me about these messages is I used to respond to them aggressively.
Mainly because they frustrated the hell out of me.
Asking what to buy implies that style is transactional. That by purchasing certain items you’ll magically start to look a certain way. I came to this shocking realization two years ago when I was cleaning out my closet (one of those days where you’re embarrassing yourself by being honest with how often you wear things).
I was stood in front of my closet which is lined on both sides with probably close to forty hoodies on each side. Good brands – FOG, Stussy, Waniki – things I actually spent money on (hello $$$ Grailed impulse buys). And I had this sudden moment of clarity: I probably wore about half of them once or twice.
Maybe. The other half looked identical in style and fit despite having cost me wildly different prices. Right next to my $400 Fear of God hoodie was a $60 Champion reverse weave that looked and fit significantly better on me.
That’s when it clicked. For years I’d been taught that style was predicated on wearing the “right” brands. Supposedly rare clothing found from GAPing til GODDAM drop kicked me into reality.
Why the fuck did I care about these pieces so much? Owning them didn’t automatically make me look put-together. Hell, I wasn’t even wearing most of them because – newsflash – they didn’t fit me that well.
It’s like that kid in high school who saved up all summer to buy a limited pair of Jordans. We walked past each other in the hall his first day wearing them, and he looked like a toddler taking steps for the first time. He moved so weird because he was worried about creasing them.
Shoes looked great, but he looked stupid. It happened so frequently with clothes I owned that I almost stopped wearing them. Instead I’d daydream about the new releases I “needed” to keep my closet fresh.
That’s when I started studying people who always looked good. All my friends who were “always dressed hoe” weren’t just hypebeasts rocking the wildest drops. There were actual dudes who didn’t swear by Supreme but knew how to wear a hoodie and look cool as hell doing it.
And do you know what I discovered? Nine times out of ten those dudes weren’t spending more money on clothes than me. They were wearing much cheaper brands but knew how to wear them exceptionally well.
My friend Carlos works at this coffee shop in Bushwick. He’s NOT on payroll, which means he’s not making Steven Nichols-type money. But if you’re ever walking down Lincoln and you pass HOM fragrant with the rich aroma of beans, everyone questions where he got his outfit from.
You know how I know? Because I ask him every. Single.
Time. He’ll wear something so simple – yet incredible – and I’m in heaven. “How the fuck do you always look so good?” I’ll ask. His secret?
Everything he owns fits him perfectly. I found out years ago he takes literally everything he buys to this old Dominican guy who runs a tailor shop right next to the bodega down the street from me. Hems his trousers for twelve dollars.
Takes in shirts for fifteen. He’ll buy a plain black shirt from Target and spend more on getting it tailored than the shirt itself costs, but it fits him so damn well it looks custom-made. I was skeptical when Carlos first told me.
Tailoring old person? Never. Thought about it a few more times, googled how much it actually costs to get things altered, and took a hoodie I knew was too boxy for me to his tailor guy. fucking friedan.
Same hoodie. Completely different garment because it now FITS me instead of hanging off my body. I’ll never forget the day everything changed for me.
Whenever I’m at home on my computer I sit with HORRIBLE posture. Hunched over, arms folded, trying not to be heard. I developed this really bad pain in my lower back and had to start physical therapy to alleviate it.
My therapist made me do these ridiculous posture exercises every day until I stopped looking like a suicide gone wrong. Emma even told me I lost weight because my body looked so different just from sitting up straight. It got me thinking about how I would contour my body when I wore clothes.
In pictures I’d always angle myself in weird positions, hide my chest and stick my gut out. I was so ashamed of taking up space, I purposely distorted myself to look skinny in photos. When I learned to stop doing that – and just sit/stand up straight – my entire outfit game improved 100%.
Posture is annoying because it’s something you have to consciously think about every day. Do I have my shoulders slouched? Is my chin tucked down?
Am I trying to disappear into my clothes? None of the above! Good posture is easy to recognise and hard to maintain.
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There’s no magic purchase you can make to fix it. Speaking of maintenance: my biggest lingering problem was that I didn’t actually take care of my clothes. I’d buy something, wear it once or twice, then let it sit in my laundry pile until I didn’t know where it was anymore.
My friend Derek has about three plain white/unmarked/uninteresting Uniqlo shirts he lives in. Each one looks crisp as hell because he actually irons and hangs them up after wearing. The tags are still on them too, because he refuses to throw them away and has had them for YEARS.
When I asked him how he keeps them in such perfect condition, he laughed in my face. “You don’t buy $150 shirts and let them get wrinkled and have ripped buttons, Ryan.” Cleaning my shoes was another game changer. I spent $200 on a pair of Jordans, wore them in the rain once, and was pissed they looked like I wore them daily for a month. Learning how to properly clean them and using spray protectant actually made my older trainers look new again.
And when I bought new ones, they STAYED new because I was rotating them more than one pair at a time. Holy shit the difference it made just by taking care of my belongings. But most importantly, I actually figured out what colours looked good on me.
Green used to be my favourite colour so I bought every bright green shirt I found (ps. this still rings true). I owned this Golf Wang hoodie that was probably the brightest orange in the world and wore it non-stop despite how hideous it looked with my skin tone. Friend of mine who does styling for photographers/textures told me bluntly, “Orange fights with your skin, man.
Stop wearing that hoodie.” What he helped me realise was that I actually look really good in muted colours. Forest greens, dark blues, black, grey. Nothing bright or crazy.
Everything meshes so well now that I can grab any shirt and it’ll match pretty much anything. Colours go along with making sure you actually match your outfit too. I used to wear so many individual wild outfits that looked crazy because each piece on its own was cool.
Camo trousers, black & white tie-dye shirt, red socks, and bright yellow shoes. Christ, think of all that colour fucking fighting for attention on my body. Now I try to make sure I’m not throwing seven different colours/patterns onto myself at once.
It helps me stay way more intentional with what I buy. As in, I don’t just buy stuff because it’s hype or new. My closet is severely smaller than it used to be but I can honestly grab any shirt, any pair of trousers, and know they’ll look good together.
Because now I only buy things that fit what I actually own. Everything serves a purpose. Part of that is actually wearing what fits you comfortably.
We’ve all been there – we see something in the mirror we think looks good so we buy it, only to realise how fucked it looks/textures when we actually wear it. Baggy jeans? Fuck around and find some that fit you well.
Tights too much? Looser jeans aren’t for you. Spend the extra money on jeans that fit perfectly in your waist and you’ll never go back.
My waist is usually shirt quiz. Either I try to wear shirts that are too tight and look like I’m drowning in my own grease or I go too loose and look like a damn tent. I eventually found my sweet spot where my shirts are fitted enough to look slim, but loose enough to where I don’t feel restricted.
Meaning I actually know what my damn size is now. Stop trying to wear shirts 2 sizes too small for the “fit.” Wear what fits you. The craziest part about all this is that NOW people actually *think* I spend more on my clothes.
Learned to wear what I have well and suddenly everyone thinks I shop at expensive stores. My girlfriend’s mum even asked me where I shop anymore. Regular-ass bodega dude asked me where I get my clothes.
People think dudes with dope wardrobes ONLY buy clothing from expensive brands. Newsflash: they don’t. Sure there are suckas out there that do and only wear designer-brand clothing.
Hell, I’ve fallen victim to that trap too before my awakening. But learning to wear what you own and own what you wear is how you get referred to as having STYLE, not just clothes. Trust me, I love rocking good brands with great fits.
My Rick Owens Jeans still feel ten times better than anything I could get from Zara. But would I rather wear that unfinished looking XO shirt that doesn’t fit me very well or a crisp white Uniqlo fitted perfectly to my body? No contest.
Clothes don’t make you look cool. How you wear them does. TLDR version: these days when dudes hit me up asking what they should buy for an event, I send them this article.
Nine times out of ten they’ll own enough clothes that actually fit them and just not realise it.
Purging my closet of things I don’t wear or don’t fit me changed my whole style and I can’t recommend doing the same enough. PS.
Still buy way too many trainers. Lord knows Emma yells at me about this on the regular. But you better believe I’m wearing them all.
Shoes don’t “air” in my closet. Hung up immediately and worn within the next month of buying. Makes me too happy.
PS. Thank you so much for reading guys. Hopefully this helped someone out there realise how to maximise what they own.
Don’t be afraid to reach out with any questions or if you just wanna talk about clothes. 📩 [email protected]
