The moment I truly understood the power of alterations happened in a tiny, fluorescent-lit tailor shop in Chicago’s West Loop about eight years ago. I’d dragged my buddy Mike there on a mission of mercy. Mike—six-foot-four with the shoulders of someone who actually uses his gym membership and legs like tree trunks—had spent three desperate hours at Nordstrom trying to find a suit for his sister’s wedding. The results were… catastrophic. Either the jacket fit his shoulders but looked like a crop top, or it covered his torso but made him resemble an American football player playing dress-up in his dad’s clothes.
“Maybe I’ll just wear a nice shirt and tie,” he’d texted me, defeated.
No. Not on my watch.
We bought the suit that fit his shoulders and chest (the important, hard-to-alter parts) and took it straight to Mr. Park, a seventy-something Korean tailor who’d been altering clothes since before either of us was born. Mike stood awkwardly on a small platform, sweating under the hot lights while Mr. Park circled him like a shark, pins in mouth, muttering measurements.
Two weeks and $87 later, Mike tried on the altered suit. The transformation was so dramatic he actually said—and I swear this is a direct quote—”Holy shit, I have a waist!”
The jacket now followed the line of his torso instead of hanging like a boxy sack. The pants broke perfectly over his shoes instead of pooling around his ankles. The sleeves showed the right quarter-inch of shirt cuff instead of swallowing his hands. He looked like he’d spent a thousand bucks on a made-to-measure suit rather than three hundred on an off-the-rack one plus alterations.
When he wore it to the wedding, his style-conscious sister pulled me aside. “What did you do to my brother? He looks… good. Like, intentionally good.”
It wasn’t me. It was the oldest trick in the menswear playbook, one that’s been gradually disappearing from American style consciousness: the simple magic of alterations.
Most guys I talk to nowadays seem to think clothes come in just two categories: stuff that fits off the rack and stuff that doesn’t. It’s a bizarre misunderstanding of how garments actually work. Clothes are designed for an imaginary average person who doesn’t exist in real life. Even models—literal professional clothes-wearers—get their outfits pinned and clipped for photoshoots. The expectation that anything should fit you perfectly without modifications is fashion’s cruelest myth.
My grandfather understood this intuitively. He wasn’t a wealthy man—worked as a butcher his whole life—but the few clothes he owned fit him impeccably because he had a relationship with his neighborhood tailor. A simple working man who never made more than a modest salary had better-fitting clothes than tech bros making six figures today, and the secret wasn’t money—it was alterations.
The lost art is finally having a small renaissance, partly thanks to online custom clothing becoming more accessible, which has reminded people that clothes can—and should—actually fit their specific bodies. But custom isn’t always necessary or budget-friendly. Strategic alterations to off-the-rack items can get you 90% of the way there for a fraction of the price.
So what alterations deliver the biggest impact for the least money? After years of trial and error (and some truly questionable early experiments, like having a tailor “slim down” a vintage leather jacket in college—sorry, beautiful jacket that I ruined), here’s what I’ve learned:
For shirts, the single most transformative alteration is “darting” the back. Most men’s off-the-rack shirts are cut straight down from the shoulders, creating that billowy excess fabric that balloons around your waist when tucked in (what my tailor colorfully calls “the muffin top in reverse”). For $15-25, a tailor can add two vertical darts in the back that follow the tapering of your torso. The result is a shirt that looks custom-made.
My buddy Trevor—you remember, Hugo Boss Jr.—takes literally every shirt he buys to his tailor for this simple fix. “It’s the difference between looking like you’re wearing clothes and looking like clothes are wearing you,” he says, which is both accurate and exactly the kind of pretentious thing Trevor would say.
The second easy shirt fix is sleeve shortening, which runs $15-20. Most guys wear sleeves that are too long, which makes their proportions look off and creates a sloppy impression, especially when layered under jackets.
For pants, hemming is obvious ($10-15), but the true game-changer is adjusting the rise. If you’ve got pants that gap at the back waistband or give you that lovely “plumber’s special” effect when you bend over, a tailor can adjust the rise in the back for about $25-30. It’s one of those invisible fixes that makes everything look better without anyone being able to pinpoint exactly why.
Tapering the legs of too-wide pants ($20-25) can also bring outdated trousers into the current decade without buying all new ones. I recently rescued a pair of beautiful wool dress pants from my dad’s “donation” pile this way. They’d been sitting there because, in his words, “they make me look like a cartoon character from the ’90s.” Twenty bucks later, they’re his new favorites.
Let’s talk jackets and blazers, which is where alterations truly earn their keep. The shoulders of a jacket are like the foundation of a house—they need to be right from the start because they’re extremely difficult and expensive to alter. But almost everything else can be tweaked.
Sleeve length is the most visually obvious alteration ($25-35). A jacket sleeve should end about a quarter-inch above your shirt cuff when standing with arms at your sides. It’s amazing how many guys get this wrong, with jacket sleeves completely covering their shirt cuffs or, worse, riding halfway up their forearms.
Then there’s the jacket waist. Even moderately priced off-the-rack jackets can look custom if they follow the line of your body rather than hanging straight down. Taking in the sides ($30-50) creates that tailored silhouette that’s the hallmark of quality menswear. If you buy only one jacket but have it perfectly altered, you’ll look better than the guy with five ill-fitting expensive ones.
My most dramatic tailoring transformation happened with a navy blazer I found at a secondhand store in Boston. The fabric was gorgeous Italian wool, the shoulders fit perfectly, and the price was a ridiculous $40. But it had clearly been made for someone built like SpongeBob SquarePants—boxy, with gorilla-length arms. I spent $75 on alterations—more than the jacket itself—to shorten the sleeves, take in the waist, and adjust the button stance. The result? A $600-looking blazer for $115 total that fits better than ones I’ve paid full retail for.
There are limits, of course. Some alterations are cost-prohibitive or technically difficult. Taking in a jacket at the shoulders usually isn’t worth it. Moving the collar of a shirt is rarely successful. And adjusting the rise of pants at the front can create weird proportions. A good rule of thumb: if the alteration costs more than 60% of the garment’s price, you’re usually better off finding a different piece that starts closer to your needs.
This is why it helps to build a relationship with a skilled tailor who will tell you honestly what’s possible. Not all tailors are created equal. The dry cleaner offering hemming services is fine for simple jobs, but for anything involving restructuring a garment, you want someone who truly understands garment construction.
Finding the right tailor is a bit like dating. I went through four before finding my current guy, a second-generation Italian-American who works out of what looks like a closet in the back of an old apartment building in my neighborhood. His waiting room is literally two folding chairs, but I’ve seen well-known designers drop off samples for him to work on. When I moved apartments last year, proximity to his shop was legitimately a factor in my housing search.
The best way to test a new tailor is with a simple job first—maybe hemming pants. See if they ask questions about how you wear them (With what shoes? How much break do you prefer?). A good tailor doesn’t just execute your requests; they guide you toward what will actually look best.
Beyond the fit improvements, there’s something deeply satisfying about the resourcefulness of alterations. In an era of disposable fashion, there’s a quiet rebellion in keeping and modifying clothes rather than replacing them. My most complimented shirt is actually a hand-me-down Oxford from my uncle that was comically large until my tailor worked his magic. It cost $32 to alter and looks better than anything I could’ve bought new for three times that amount.
Alterations also give you shopping superpowers. Sales racks, vintage stores, and even hand-me-downs become viable sources of amazing clothes when you’re not limited to things that fit perfectly off the bat. That designer jacket marked down 70% because it’s the awkward size no one wanted? Buy it if it fits in the shoulders and let your tailor handle the rest.
I’ve seen too many guys dismiss potentially great pieces with “That’s not my size” when minor alterations would make them perfect. We’ve been trained to think of clothes as fixed, finished products, when they’re actually more like 80% finished products awaiting the final touches that make them truly yours.
So here’s my challenge: Take one item from your closet that you never wear because the fit is slightly off. Maybe it’s a shirt that’s too baggy, pants that are too long, or a jacket with gorilla arms. Spend the $15-30 to have it altered properly. I guarantee it’ll become one of your favorites, and you’ll be hooked on the transformative magic of this lost art.
Mr. Park retired last year. When I went to pick up my last pair of altered pants, he told me, “Young people don’t understand clothes anymore. They buy, they throw away, they buy again.” He sighed. “But you understand. You bring your friends. This is good.”
It is good. And if more of us rediscover this simple way of making ordinary clothes extraordinary, we’ll all look a hell of a lot better without spending a fortune to do it.
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