Editor’s Note: This article was originally published in June of 2019 but continues to be one of our most popular articles of all time. We’re republishing it here to celebrate its 4th anniversary on the site. Let me tell you about the time I embarrassed a fashion executive at his own dinner party.
We were talking menswear – I love these kinds of conversations with strangers at parties – and he had on what I think any dude would consider the gold standard of wardrobe basics: A great fitting navy blazer worn over a white oxford and dark jeans. As he was talking about his blazer, I couldn’t help but notice and compliment his shirt. “I love that shirt!” I gushed. “Is that the new Thomas Mason for J.Crew?” I had just written about their collab a few weeks prior. He looked at me funny for a second, and then laughed nervously before quietly mumbling that yes, it was exactly what I thought.
The irony was not lost on me that he was wearing a $98 J.Crew shirt whilst mine literally costs 3x as much from a brand that retails blazers for $750+. We made small-talk for a minute before other people came to join us in the kitchen and he leaned in to whisper: “You know, I wear stuff like that almost every week.
Like half of my daily wardrobe is easily accessible basics.” There was a moment of silence. “I guess the key is knowing which ones look expensive.” He finished.
This conversation has stuck with me all these years not simply because a seed had been planted that many of my stylish companions were taking intentional style shortcuts I’d previously condemned them for; but more so because I had effectively been telling myself this exact same thing for years now. Simply put, I had been giving myself permission to do what I had always done best: hunt down the holy-shit-is-that-under-$100-it-must-be-a-dupe pieces of the clothing world. Ok, but first let’s get one thing straight.
When I say something is under $100 and looks as expensive as something 3-10x the price I am not saying that a $20 jumper is equal in quality to a $600 jumper. I’m not stupid. That would be absurd.
Usually, there is a very real and justifiable difference in materials, construction, care, longevity, etc. when comparing middle and upper market prices. What I am saying is there are iterations of these “basics” that offer you about 90% of the feel and look of higher-end goods but at about 20% of the price. I have spent years honing my eye for these particular items and have developed a personal database of insanely versatile basics that even the most “trainer-onspective” knows I couldnt possibly afford.
Sure, I still love grabbing vintage outfits when I can – there’s nothing like a vintage outfit to really make people think you spent way more than you actually did – but outside of that I stick to this highly-curated list of classics that “look expensive.”*Below I’ve outlined some of my favourites that I think everyone should own in their wardrobe. *Insert your own Dad joking “these new-age iPhones” joke here. The White Oxford That Costs Way Less Than Your Dad Thinks It Does We’ll begin at the beginning. The white oxford cloth button-down is where my affinity for “cheap clothes that look expensive” began.
I ruined what was then an incredibly expensive oxford by forgetting I had a pen in my pocket (yes, rookie mistake) and was in desperate need of a replacement shirt before a major fashion event a few years back. Not having time to make it to my local shop I ducked into the nearest mall and picked up a $58 generic-brand American apparel oxford. The fabric has great weight to it with a touch of texture that’s hard to see but makes all the difference.
The collar rolls beautifully without any collar stays (you can tell it’s a real oxford by the lack of cardboard up top) and most importantly has actually got better with age. What makes it work: The primary reason this shirt passes as high-end is the thickness of the weave. Most cheap oxfords feel thin and paper-like.
This one has some serious heft to it. It’s got enough give that it doesn’t feel stiff but doesn’t drape like a rag eitther. How to style it: As far as oxfords go, I roll my sleeves to mid-forearm as opposed to fully buttoning.
This creates a much more casual (and thus higher quality) look. My trick is to never tuck it in. Button it up and wear with dark jeans for an outfit that looks put together without screaming “I’m wearing a fancy dress shirt!” The Japanese Selvedge-Adjacent Jeans Jeans have the widest price range of any clothing item.
Literally you can spend $30 or $300 and have a great pair of jeans. There are also tons of options in between that you’ll spend way too much money on because American Eagle used the words “raw” and “dyed” in the title. I have tested (yes, I am aware how douchey that sounds, I have kept meticulous spreadsheets on how my jeans fade) countless jeans over the years trying to find a “value” option that I loved as much as my pricy Japanese selvedge options.
I have finally found one that gives me about 85% of the same joy. They’re ridiculously rigid with just enough stretch (1-2%) to break in nice over time without losing their shape. They fade evenly all over rather than just the thighs and knees which blow out prematurely.
The denim has great texture due to the tight weave. What makes it work:Like all good denim it’s 13.5oz. which is about the sweet spot for modern jeans. The other thing I love about this denim is that it hasn’t been overly processed to look worn.
They start out uniformly dark and actually get nice wear patterns over time as you would expect from an expensive pair. How to style it: My biggest styling tip with these jeans is to wear them with slightly nicer footwear and accessories. They look highly convincing when your entire outfit isn’t riding on the promise that you’re wearing expensive jeans.
The Merino Jumper That Won’t Pill Knitwear is almost always where cheap brands cut corners. There’s no hiding sloppy knitting or low grade material like there is with other clothing categories. Within a few wears you can spot a $50 jumper by how it sags, stretches, pills, and just looks sad.
After being gifted a merino jumper by a brand I knew gave absolutely zero fucks about material quality (looking at you who?? ), I was thoroughly impressed when I didn’t notice any of the above after wearing it on heavy rotation for a season. Yes it’s not as fine as the $250 Italian wool version of the same jumper, but it feels substantial and isn’t doing any of the horrible things cheap jumper tend to do after a few washes. What makes it work: It all comes down to the fibre quality and knitting tension.
This jumper uses long-staple wool fibres that are knit tighter together which help resist pilling and helps it keep its shape. How to style it: I think this jumper plays especially well under a sport coat or blazer. The high quality of the merino is slightly elevated from your average crewneck making it look slightly more luxe when layered with shirts that have some texture to them.
Think of expensive vs cheap t-shirts. The PERFECT Tee Arguably the hardest “basic” to get right. Too thin and they scream cheap, too thick and they lose all charm.
There is no breakage in terms of tee shirts, only layers of bullshit you pay for. I literally tested every option out there (yes I have a sock drawer full of white tees that serve as physical reminders of my failures) before finding the holy grail. At $32 this pima cotton crew neck airs slightly looser than your average launch -pad tee but still retains that perfect weight so it hangs on your body without feeling bulky.
The neckline is also reinforced so it doesn’t stretch out like every othercheap tee. The sleeves also break right at your wrist giving you that superhero look we all strive for. What makes it work:Here’s the thing.
This tee uses long-staple pima cotton with a very tight knit which gives it that subtle sheen that most expensive brands have. How to style it:T-shirts should always be styled loose. If you see your baby arms or bellybutton thats too tight.
This white t looks insanely expensive when left untucked with jeans but can be dressed up tremendously under a sport coat. The Cashmere-Adjacent Beanie Winter accessories are the worst. Every brand and their mother knows you can slap “cashmere” on a beanie and mark it up five times what it costs to manufacture.
I actually lost my favourite expensive cashmere beanie in a taxi and had to resort to ordering this $38 option off the men’s best basics branding john owned with my coworker. I was blown away at how soft the material was. Turns out it’s a cashmere-wool blend that is way denser than 100% cashmere hats typically are.
It traps heat way better than my lost Beast kaufen Original version and doesn’t unravel like most hats that cost less. What makes it work: When brands cut corners with cashmere they typically use 100% cashmere. Problem is that fabric is so soft it doesn’t hold its shape very well.
This blend is tight knit with just enough wool to keep the beanie looking styled. How to style it: I actually fold mine once as opposed to double cuffing like you often see. It creates a more relaxed, editorial look.
The Minimal Trainer That Doesn’t Look Like a Child’s Slipper White leather trainers are the bane of my existence. Some brands charge $600 for the exact same silhouette that you can get at Target. I have worn through multiple pairs at all different price points but have finally found a white trainer that gives me about 90% of the satisfaction of my pricey Instagram favourites.
Sure they aren’t butter-soft calfskin that feels like they’re itching to come off your feet but they are deliciously minimal and the leather actually softens with wear. They also don’t have any crazy stitching or exaggerated shapes that are desperately trying to look like something they’re not. What makes it work: There are two details that make these trainers look much more expensive.
First, the design is minimal. Period. There are no weird branding details or embellishments that scream “LOOK HOW MINIMAL I AM.” The sole is also just stiff enough that it doesn’t look like kid’s slippers.
Most brands make the mistake of having too thin of a sole with these types of trainers. How to style it: Again, let these things get slightly worn in before you rock them. You’ll instantly channel that coveted “I paid $2000 for these” vibe everyone is going for.
The blank canvas of a white trainer also allows you to really lets your outfit shine. I pair mine with everything from suits to shorts. The Unstructured Blazer That Doesn’t Suck You know what guys cheap out on at their own peril?
Tailored clothing. Construction details like canvas that give suits and jackets their structure are extremely hard to replicate at an affordable price point. That being said, I was pretty shocked when I stumbled upon this unstructured cotton blazer that has barely received any hype but feels virtually indistinguishable from $300+ versions.
The reason this jacket works is because it doesn’t pretend to be something it’s not. There is no artificially added structure with fusible materials that will stretch and look weird after you wear it a few times. It’s unstructured down to its core with soft shoulders and a perfect amount of lining to keep it from slipping.
What makes it work: The trick is in the fabric they used and the actual cut of the shoulders. The cotton is heavy enough to provide structure on its own while the shoulders slope naturally instead of being stuck straight out. How to style it: Once people ask you where this moderately-priced jacket is from you’ll know you’ve successfully styled it.
Wear it as you would typically reek of desperation and commitment to menswear twitter. Unbuttoned with sleeves slightly pushed up and an oversized tee underneath. Embrace the overscale nature of the jacket rather than trying to make it look something it’s not.
The Chambray That’ll Make You Question Your Japanese Fabric Obsession Ah chambray. Bestowed worshipped upon by men’s style media for what literally amounts to cotton shirts with white weft threads showing. Guys drop hundreds of dollars on chambray shirts from Japanese textile factories like the uneven texture is going to magically make them look like The Dude.
I have hunted high and low for years trying to find an inexpensive chambray that can go toe-to-toe with these $200+ journalistic nightmares. Guys still gravitate towards China Blue like it’s 2012. Rip those shirts off and cheque out this bad boy I picked up for $68.
Not only does it have the coveted textured fabric with white weft threads, but it even comes with vintage-inspired details like cat’s eye buttons and a pocket pen slit. Yup, they thought of everything. What makes it work: Like all great chambray the fabric is where this shirt shines.
Unlike generic chambrays that use a uniform dying process the white jeans from this shirt are intentionally uneven creating a richer blue. How to style it: I wear mine with the sleeves rolled and a narrow double cuff showing. Since the shirt itself is the statement piece here I try to keep the rest of my outfit simple.
A plain white tee works well here or even a light coloured henley. The $75 Chinos You Won’t Immediately Recognise As Affordable Ah trouser shopping, the worst. Between poorly constructed fabrics, ill-fitting slides on the hips, and pockets that gap at the seams I may have spent more money trying to find the perfect pair of chinos than I care to admit.
Now don’t get me wrong there are definitely some great affordable options out there. But good lord do they not come easy. The cotton twill used in these is incredibly dry to the touch with virtually no sheen.
The rise is impeccable, not too low like awful 2000s khakis but not as outrageously high as you might see with more modern styles. They also fit through the seat and thigh better than most $200 trousers I’ve owned. Literally unraveled.
What makes it work: The holy grail of details that make these so special is the waistband and rear pockets. Most affordable brands skip stabilizing the waistband with cotton canvas which causes them to roll after you wear them. These have been properly constructed with an internal canvas lining that you can’t see.
The rear pockets are also placed at just the right angle to actually look good on your ass. How to style them:I cannot stress this enough. Get your jeans hemmed!!
It’s the single most important thing you can do to make your clothing look expensive and folks selling $75 jeans know it.
I have mine tailored to break slightly over my loafers or with a small cuff that touches my trainers. TLDR Alrighty!
There you have it my favourite clothing items that legitimately look expensive yet cost way less than you’d think. I will say that finding these items does take lots of trial and error, and I still buy things that look cheap as fuck all of the time. I simply choose to focus on these brands more because I know I can trust them to not look cheap.
Also, I don’t have the patience or money to waste on getting something tailored that looks terrible. Sure there is a difference in sustainability, ethical practices, and longevity between expensive brands and these guys. But the $88 jeans aren’t going to feel like silk and age quite as nicely as your luxury pairs.
However, if you’re looking to spice up your wardrobe without breaking the bank or suck up to your tailor these basics will serve you well. Let me know your picks in the comments. I’m always looking to add to my list!
