December 5, 2023


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The Essential Shoes Guide: Timeless Pairs That Every Guy Should Own

Which men’s shoes have stood the test of time? Trends come and go, but there are a handful of stalwart styles that won’t be disappearing anytime soon. Some, like the Oxford, are turn-of-the-century relics that have been cemented into the formal footwear canon. Others, like Adidas Stan Smiths, have a vintage appeal that gets even better with age.



Rather than chasing fads, it’s important to have a few pairs of versatile men’s shoes in your closet that you can wear—and look good in—for years to come. We spoke to New York-based fashion stylist Seppe Tirabassi and got his picks for the essential shoes every man should own, plus his advice on when to wear them and how to pair them.

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Essential Men’s Shoes Every Guy Should Own

Sebago Classic Dan Loafer
Sebago Classic Dan Loafer Courtesy Image

1. The Penny Loafer

“A loafer is a must-have for any guy because it works double-time as both a dressy shoe and a casual shoe,” Tirabassi tells Men’s Journal. “When you don’t feel like adulting and tying your laces, you can slide into a loafer after throwing on a pair of ripped jeans and a T-shirt. It’s an effortless way to elevate your look. And of course, wearing loafers with a suit is perfectly acceptable for any formal dress code, except for black or white tie.”

Our Picks:

  • Sebago Classic Dan [$260;]
  • Ermenegildo Zegna Brown Marcello Loafers [$985;]
  • G.H. Bass Logan Croc Weejuns [$145;]
Clarks Desert Boot
Clarks Desert Boot Courtesy Image

2. The Chukka (a.k.a. the Desert Boot)

The chukka is a classic men’s ankle boot, and it’s a great pick for cooler weather in the fall through the spring. Chukkas generally have uppers made from leather or suede that’ll soften and mold to your foot over time, and Clarks Desert Boots have the added bonus of a bouncy rubber crepe sole.

“For me, the perfect moment for wearing a chukka is when you’re grabbing a coffee and going for a nice Sunday stroll in the park,” Tirabassi says.

Our Picks:

  • Clarks Desert Boot [$150;]
  • Cole Haan York Chukka [$250;]
  • Banana Republic Brendt Leather Chukka Boot with Crepe Sole [$178;]
Polo Ralph Lauren Bryson Leather Chelsea Boot
Polo Ralph Lauren Bryson Leather Chelsea Boot Courtesy Image

3. The Chelsea Boot

“Few boots are as versatile and timeless as a Chelsea boot,” says Tirabassi. “They go with pretty much anything that’s in your closet from the fall through the winter and the spring.”

Chelsea boots are made with all kinds of leather and suede (even exotic ostrich leather), and you’ll find them in a range of colors.

“The streamlined shape of a Chelsea instantly elevates an outfit without looking like you’re trying too hard,” Tirabassi says. “And because they have elastic sides instead of laces, they’re easy to slip on and really comfortable.”

Our Picks:

  • Polo Ralph Lauren Bryson Leather Chelsea Boot [$195;]
  • Karl Lagerfeld Paris Chelsea Boots [$275;]
Cole Haan Modern Classics Wingtip Oxford
Cole Haan Modern Classics Wingtip Oxford Courtesy Image

4. The Oxford

“Just like every man needs an expertly tailored suit stashed in his closet, he also needs a solid Oxford shoe to go with it,” Tirabassi says.

No matter what kind of formal occasion you have on the calendar, an Oxford shoe is a solid footwear choice. Tirabassi advises shelling out for a quality pair—these shoes are reserved for special moments, after all, so they should look (and feel) good. Better yet, if you take good care of them, one pair of Oxfords could easily last a lifetime.

“Wish I could say the same thing about a suit,” says Tirabassi. “Waistlines change as you age, but your shoe size? Not so much.”

Our Picks:

  • Cole Haan Modern Classics Wingtip Oxford [$300;]
  • Church’s Shannon Plain Toe Oxfords [$880;]
  • Dr. Martens 1461 Smooth Leather Oxford Shoes [$120;]
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Birkenstock Arizona Soft Footbed
Birkenstock Arizona Sandals Courtesy Image

5. Birkenstock Arizona Sandals

Birkenstock Arizonas are unusually versatile for a pair of sandals. First, they come in a wide range of colors and materials to match any wardrobe or style preference. Second, you can wear them to the beach, around town, and even with a pair of thick wool socks (something that would be a cardinal fashion sin with other sandals). But their best quality might be how easy they are to wear.

“Ever since I started wearing Birkenstocks as a kid, I still haven’t found a pair of sandals more comfortable than these,” says Tirabassi. “I’ve never not had a pair or two in my closet.”


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Adidas Stan Smith Shoes
Adidas Stan Smith Shoes Courtesy Image

6. Adidas Stan Smith Shoes

“Everyone needs a simple white sneaker on their shoe rack, and this is the one to get because it’s both timeless and retro-feeling at the same time,” says Tirabassi. “You can wear them with literally anything, from shorts to jeans—even a suit if you want to make a statement.”

The decades-old model now comes in a wide range of colorways, but it’s a good idea to start with a classic white pair. (Check out our white sneakers guide for other stylish options.)


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Vans Checkerboard Slip-On
Vans Checkerboard Slip-On Courtesy Image

7. Vans Checkerboard Slip-On

“There’s something to be said about footwear that you can throw on quickly when you’re running late,” Tirabassi says, “and I always keep a pair of Vans by the door for that reason.”

He’s worn Vans Checkerboard Slip-Ons since elementary school, and they’ve served him well as inexpensive men’s shoes for everyday wear. If you’re not into the checkerboard pattern, Vans has many solid-color options as well.


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Original L.L. Bean Boot
Original L.L. Bean Boot Courtesy Image

8. Original L.L. Bean Boot

“I grew up in Maine, and I can’t remember a winter spent without these boots,” Tirabassi says. “They’ll keep your toes dry and warm in the rain, slush, or snow, and they’re very comfortable with a pair of thick socks.”

They’ve become a style icon, too: He has seen them worn on the streets of Tokyo, and Todd Snyder recently unveiled a limited-edition version with an eye-catching plaid upper.


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New Balance 327
New Balance 327 Courtesy Image

9. Athletic Sneaker

“Think of this pair as your everyday sneaker, but not one that you’ll wear at the gym,” says Tirabassi. “In other words, you want to keep these clean, sweat-free, and ready to show off.”

Instead of helping you work out, these men’s shoes will be your go-to pair when you need something comfortable but also stylish—on a long flight, for example, or while running errands around town.

“Whether they’re New Balance or Lanvin, almost every menswear label designs casual sneakers with their signature spin. No matter the budget, you’ll find one that speaks to you.”

Our Picks:

  • New Balance 327 [$100;]
  • Lanvin Bumper Low-Top Sneakers [$455;]
  • Veja x Rick Owens Performance Runner V-Knit [$290;]
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