If there’s one secret the fashion industry doesn’t want you to know, it’s that price and quality don’t necessarily correlate. It’s a tough pill to swallow, especially for those of us who love clothes and spend way too much money thinking about them. I came to this realization six years ago when I arrived in Milan for Fashion Week wearing what I thought was a standout outfit.
Perfectly tailored blazer from an up-and-coming Brooklyn workshop, trousers from an innovative Japanese line that had recently started exporting to the US, handmade loafers that cost me almost an entire month’s rent… I felt like such a badass until an Italian editor I admired took me aside and said “Nice T-shirt. Whose is it?” My T-shirt. The plain white crewneck I’d snagged from a three-pack of tees I bought at Target for $19.99 four years prior.
It had molded perfectly to my body after dozens of washes, reached that Goldilocks zone of not-too-tight-yet-still-fitted, and somehow looked better than every expensive tee I’d ever purchased. Which led me to my first revelation – sometimes, the cheapest items in our closets outperform everything else we own.
Now, after writing about men’s style for over ten years, building what is frankly an obscene wardrobe that’s caused the floors of my flat to buckle (my landlord is still not over it), and testing products at every price point imaginable for work and play, I’ve developed a hypothesis: Every fashionable person has at least a few cheap things they love more than their expensive equivalents.
That $8 baseball cap from Target that fits their head better than any you’ve ever tried on at American Safari. The cheap sunscreen from CVS that’s somehow more effective than any number of expensive French-imported brands I’ve tried. The bargain pair of jeans from Uniqlo that seem to soften with wear while the $400 Japanese selvedge you “own till they die” remains stiff and unworn in the back of your closet.
And with that, I give you my theory proved: here are the least expensive things in my wardrobe that consistently steal the show and earn me the most compliments (and questions about where I got them). Let’s kick things off with something almost too obvious: socks. Don’t laugh – hear me out.
The most complimented item in my entire wardrobe is $1.50 a pair. Yes, socks. Specifically, Uniqlo colour socks that are sold in every colour of the rainbow and then some.
I have at least 25 pairs in every shade ranging from burnt orange to forest green to mustard yellow (trust me when I say that mustard yellow matches with everything from jeans to suits). Once a week, at least, someone will notice my ankles and ask “Hey man, where’d you get those socks?” Usually whilst wearing a full outfit that cost more than I make in a month. My response? “Oh these?
They’re Uniqlo.”. Sure enough, I pull out my phone and show them there are endless options they can get in store RIGHT NOW. “Dude, those are way nicer than the ones I was going to get at American Apparel!” etc. etc. The colour selection is unparalleled, they’re thick enough without being too bulky, and they haven’t faded or lost their shape after dozens (okay, hundreds) of washes.
I’ve bought pricey socks from every brand known to mankind, and I always come back to these babies. The only downside is Uniqlo rotates colours based on season, meaning I’ve sprinted down to their SoHo location in panic more times than I care to admit when I heard they restocked the exact shade of olive I’m looking for. White Oxford shirt – Spier & Mackay ($58) White shirts can be hit or miss.
If you don’t get the fabric or fit quite right, they can instantly look dated or cheaper than they are. Spier & Mackay is a relatively new Canadian brand that operates almost exclusively online. All of their products are priced well below your typical American brands, making Brooks Brothers look like they’re gouging their customers.
Case in point – their Oxford cloth button down is only $58. That’s not exactly dollar store cheap, but it’s also perfectly reasonable compared to the $185+ versions coming out of the American brands with fancy “heritage” stories. Here’s the thing though – their fabric is WAY better than what most brands are using these days.
Hefty with the perfect amount of texture, incredible collar roll* (I know, weird flex if you’re not a menswear nerd – trust me when I say this matters), and after about three washes it develops that perfectly worn-in look all great Oxford shirts have. I own six of these bad boys in different colours and weights now, and reach for them more often than my nicer oxfords that cost triple the price. *I didn’t used to care about collar roll at all, but trust me when I say spending thirty seconds on Google will have you salivating over that perfect spin. Surprise denim hero – Gap ($48) I can’t believe I’m writing this, but hear me out.
This Joe’s Jeans alternative isn’t from some tiny boutique I found on my latest trip to Tokyo. It’s not from a high-end designer I’m ashamed to admit I love (looking at you, Ermenegildo Zegna denim). It’s denim from – wait for it – GAP.
The original Gap, not even their “better” line. I found this sucker on the clearance rack four years ago for $38 and snatched it up as something I’d wear around the house and for weekend activities where I didn’t want to sweat my actual jeans. Little did I know how great they were.
They’ve faded in all the right places while maintaining their structure and shape in the legs and pockets, and the cut is somehow effortlessly stylish without trying too hard. I wore this jacket to a work event last month in Los Angeles and had an actual stylist reach me after speaking to clients to ask where I’d found this “perfect vintage denim.” Her jaw didn’t stop hitting the floor all morning when I told her it was from Gap, buyded 2021. Now it lives in my suitcase more than my drawer – it’s unpretentious, comfortable, and for whatever reason gives off some serious cool-guy vibes that my anxiety-riddled soul does not emit on the inside.
Chinos I wear more than my$$$ brands – Wrangler ($24) Remember Wrangler? Yeah, that brand that your dad or granddad was wearing when you thought jeans ended with mum’s getaway jeans from Loft. Well they make a line now called Wrangler Performance Series that look like they’re your typical stretch chinos, but cut more like slim-fitted jeans.
They were amazing. High enough waist to prevent them from falling down like some chinos I own, substantial feeling fabric without being too heavy or hot, and the subtle stretch makes them feel like you’re wearing baggy pajama trousers. Softened up over time while still holding their shape, they’re what I pack for any trips that involve red-eye flights or days of exploring on my feet.
Washes way better than any “travel chino” I’ve ever owned (including the ridiculous $120 travel chinos that are supposed to be wrinkle resistant), and look sharp enough that I’ve worn them directly from the plane to meetings. I’ve shocked fancy-trousers friends more times than I can count by telling them what brand they are – there’s still such a stigma around “mall brands” that we carry as innately inferior when a lot of them make stuff way better than people give them credit for. Grandpa Tee – H&M ($15) Yep, you read that right.
Since college I’ve been buying H&M’s Premium Cotton t-shirts and haven’t looked back since. They run slightly thicker than your typical H&M tee, but in a flattering slightly-boxy cut that immediately looks more intentional than your average tee. A word of advice here – buy them a size SMALLER than you normally would.
Then put them through the wash with hot water once to shrink them up. bam – perfect size. They’ve lasted me four+ years at this point and I’ve gone through dozens. I’ve tried literally every brand from the $6 Muscle Shirts your dad buys at Gildan to $85+ artisanal Japanese cotton shirts spun by true weavers of the threadt, and these hit that magical middle-ground of just-the-right-fit, just-the-right-weight, and wear like a dream.
I have a whole drawer dedicated to them at this point and pull them over fancier shirts all the damn time. Pair of eyeglasses ($95) Raise your hand if every time you wear glasses someone tries to convince you they’re vintage Persol/Oliver Peoples/etc. Okay now raise your other hand if they actually are. *points at no one* kidding – those of you with raised hands go buy some cheap earrings and cheat.
Buy me, on the other hand, I’ve been rocking the same frames for almost seven years and people STILL don’t realise they’re from Warby Parker’s standard collection. Quality is definitely on par with more expensive frames I’ve owned that cost four times as much, and optically they’re great. My prescription is weaker than it used to be, so I may need to take another trip to get new lenses someday, but for $95 inclusive of scratch-resistant lenses this was a no brainer.
Arguably the coolest part? They don’t look cheap! Not sure why people automatically think glasses with thin arms are pricey but I’m not complaining.
Watch – Seiko SPB143($1,125) Before you roll your eyes and mutter “Jimmy, come on you live in New York you’re probably talking about that Rolex you can’t wait to get” let me explain. Many of my friends and colleagues who cover watches for a living or collect as a hobby have Rolex and Omega watches that cost more than my car. I came into this with an open mind and a budget of around $1500 max.
Almost all mechanical watches I tried blew right past that for the movement alone, so I started looking at automatic watches. Sure they still cost over $1k, but at least I’d be getting something for my money! A few brands stood out to me but none as much as Seiko, and specifically the Seiko SPB143 “New Core” line.
This beauty right here, to be exact. Vintage-inspired without trying too hard to copy any one piece, impeccable build quality, and something as appropriate worn with a t-shirt as it is with a suit. Best of all?
Guys who actually know about watches LOVE it. I’ve had multiple friends’ wives ask where I got it when we’ve gone out because they’ve received so many compliments. Nobody bats an eye when I wind it up every night either – a big concern with cheaper automatic watches.
My_movement keeps excellent time and I don’t stress when it bangs against a doorframe like some of the expensive “status” watches my friends own. Shoes – Clarks Desert Boots ($140) Ah shoes, the one area where I will concede that price DOES mostly equal quality. That being said, there is ONE pair of shoes in my entire rotation that I feel outsells their price.
Those would be the good ol’ Clarks Desert Boots in sand suede. Yes, those same boots I somehow managed to avoid scoffing at until I was well into my 30s. They’ve been around forever, and you probably remember your grandparents or college campuses wearing them in 2010.
I’ve had mine for five years now and they STILL look better than ever. Softened up to my feet perfectly, developed a nice patina that makes them look substantially more high-end than they are, and have seen me through more moderate weather than any other shoe I own. Sure, they’re not my go-to for formal events – no menswear shoe except my custom brogues will beat handmade leather in Italy.
But for casual, smart-casual everything these guys reign supreme.
Bonus points for actually being stylish for a reason – they were worn by Jamaican rude boys in the 1960s because they looked cool, not because they were cheap. Buy cheap when you can.
I’ll say it again for the people in the back – BUY CHEAP WHEN YOU CAN. High quality clothing, shoes, and accessories absolutely do cost more and usually for good reason. Everything I listed here except the socks and tee-shirts are well above what I would typically recommend someone spend on a single item.
But that doesn’t mean there aren’tExceptions to every rule. The older I get, and the more I learn about how fashion works, the more I realise that there’s a huge swath of amazingly stylish folks out there who aren’t dropping $400 on a tee-shirt because they know better. They know that sometimes a blank canvas like that H&M tee I mentioned can take you further than you realise.
So next time someone compliments your outfit, maybe that overpriced watch or designer jacket isn’t the hero of the story – maybe it’s that perfectly worn-in $30 sweatshirt keeping it real. Fashion’s dirty little secret isn’t that cheap clothes can be better than expensive ones – it’s that the stylish people have known this for years. They’re just smart enough not to brag about it in public (especially at fashion week).
