How to Dress Like a Man: The 2026 Update

My partner John LeFevre wrote the original version of this in 2016, and updated it in 2018 and 2019. The 2018 edition got 6,500 claps and more than 100 responses on Medium, a lot of them angry, which is how you know it worked. Here's the 2026 update.

John's thesis still holds: "The problem with men's fashion is that people try too hard or not at all." For most guys, especially at work, dressing is a risk/reward decision. Live in the safe zone, keep it simple and get the fit right. That won't get you on the cover of GQ. It will get you taken seriously in every room that matters.

What changed since 2019? Offices went hybrid, everyone got more casual, and the bar dropped even further. That's good news for you. Here's everything you need to know.

Prices below are from each brand's U.S. site as of October 2026.

Suits

Own two before you own anything clever. Navy and charcoal. Two-button, notch lapel, single-breasted. John's 2016 line still works: "You can't go wrong with a two-button, notched-lapel suit." Those two will cover every interview, wedding and funeral in your twenties.

Start off the rack, then tailor it. Suitsupply's navy Havana suits start around $499, and the Lazio in S110s wool is about $698. Then budget for alterations.

Then get one custom navy suit. This is my rule, not John's. Spend about $1,500 and ask to pay in installments. It's my one exception to never using buy-now-pay-later for clothes. You'll wear it 50 times in your twenties, and it'll keep you honest about your weight.

Skip the flair. No pleats, no cuffs, no three-button, no double-breasted. John's verdict on the last one: "absolutely no double-breasted, unless you still sleep on a waterbed." If a suit is too distinctive, the only thing people remember is how often you wear it.

Brown suits are still for back office guys. Grey and navy, with the occasional pinstripe. That's all you need.

Shirts

White and light blue, spread collar. A stiff spread works with or without a tie, and with jeans or a suit.

Mizzen+Main is still the best off-the-rack option. John called it "by far the best shirt I've ever owned" in 2018 at $125. The Leeward dress shirt is $158 now. Machine washable, doesn't wrinkle, works tucked or untucked.

Get it tapered. If you want to see how bad a blousy shirt looks, John's advice still stands: watch old Seinfeld reruns.

No monograms, no shirt pockets. And wear an undershirt. It makes your shirts last longer and stops the sweat marks.

Business casual

Burn the fleece vest. John called the midtown uniform of Oxford shirt, chinos, loafers and a Patagonia vest "a fashion crutch." It still is. In 2018 he suggested a $999 Tom Ford cashmere sweater instead. You're 25. Quince's Mongolian cashmere crewneck is $59.90, and nobody will know the difference.

Swap the khakis for dark jeans, office permitting. Mott & Bow, which John recommended at $118 in 2018, starts at $119 for men now. Dark wash, no rips, no fading you didn't earn.

A blazer shouldn't look like an orphaned suit jacket. Get one in a texture (hopsack, flannel, tweed) so it reads as its own thing.

Save the golf shirt for the golf course. Nobody needs to see you miming swings in the office.

Shoes

Spend here. John's math in 2018: "Decent $700 shoes will last 3–4x longer than something you pick up from Nordstrom for $300. Do the math." The 2026 version: Allen Edmonds' Park Avenue is $450, and their factory resole package is $150. A Goodyear-welted shoe can be resoled again and again. A cheap glued one goes in the trash. I break down the math in Expensive But Worth It.

Loafers are fine with a suit now. John was right about this before everyone else. No square toes, ever.

Black with a suit if you're not sure. Brown with business casual. Match your belt to your shoes.

Cedar shoe trees are mandatory. John paid $34 in 2018. Woodlore's are about $29 a pair now. They pull out moisture and keep the leather from creasing. Cheapest way to double the life of a shoe.

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Socks and underwear

Buy one kind of sock and replace them all at once. John: statement socks "don't add flair or personality. They just make you look British." Ten or twenty identical pairs, refreshed every six months. Sorting socks is a waste of your life.

Replace your underwear more often than you think. If you can't remember when you bought it, it's time.

Ties

Three or four great ones beat fifteen cheap ones. Spend $150 to $250 each. Navy, a dark green, a burgundy, a subtle pattern. Zegna, which John recommended at $118 in 2018, now runs about $250 at Nordstrom.

Half Windsor, ending at the middle of your belt buckle. John: "A bad tie knot is like a weak handshake."

No Hermès until you've earned it. John's line for junior bankers still applies to everyone under 30: "You have to earn it."

Always wear one to a wedding or a funeral. And keep a spare in your desk drawer.

Watches and accessories

You don't need a Rolex in your twenties. John put it best: "wearing a Rolex is like driving an Audi. It means you have a little bit of money, but not much to say." And: "not wearing a watch is the new Patek."

Jewelry is a watch, a wedding ring and cufflinks. That's it.

Good sunglasses. John found Christopher Cloos early, and they still make clean, simple frames. Sunglasses go on your face or in your pocket, never on the back of your head.

No backpack with a suit. John: "Grow up, and get an adult bag." The straps wreck the shoulders you paid your tailor to fix.

The gym

No baggy mesh shorts. John has sworn by Birddogs since 2015. They were $55 in 2018 and about $78 now.

Spend less time on the treadmill and more time playing a competitive sport. John's line: "the squash court is an extension of the office." Pickleball counts.

How it should fit

Fit beats brand every time. A $300 suit that fits beats a $3,000 suit that doesn't. Five checks:

Shoulders. The seam ends where your shoulder bone ends. A dent below the seam means it's too big, and that's the one thing a tailor can't really fix. Buy for the shoulder and alter the rest.
Collar. The jacket collar sits against your shirt collar, with about half an inch of shirt showing at the back. No gap.
Button. Fastened, the front lies flat. If the fabric pulls into an X, it's too tight.
Sleeves. End at your wrist bone, with a quarter to half an inch of shirt cuff showing.
Trousers. Touch the top of your shoe with a slight break or none. No puddles at the ankle.

And three rules people forget: never button the bottom button; button when you stand and unbutton when you sit; and cut the stitching on the vents and the label on the sleeve before you wear it.

Never wear

A fleece vest over a suit.
A short-sleeved shirt with a tie.
Square-toed shoes.
Cargo shorts anywhere but a campsite.
Jeans that were ripped at the factory.
A pre-tied bow tie.
A shiny suit.
A "going out" shirt. John: "There is no such thing as a 'going out' shirt, especially on a first date."

Grooming, briefly

Haircut every three to four weeks. Cologne nobody can smell from five feet away. Moisturizer in your desk or gym bag. Whiten your teeth. The full list, with prices, is in The 15 Best Grooming Products.

The bottom line

This is still about risk/reward. Most guys aren't fashion experts and don't need to be. Two suits that fit, good shoes you take care of, white and blue shirts, no logos and no gimmicks. Do that and you're ahead of 90% of the men in the room.

And don't forget the coat. For half the year in Chicago, nobody sees your suit. The Overcoat Investment is the next thing to read.

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Forward this to a guy who still wears a fleece vest to the office.

Original versions by John LeFevre: "How To Dress Like a Man" (Medium, September 2016), "How To Dress Like A Man" (2018 edition) and the 2019 update. Quotes are his.