16 Business Casual Shoes That Work Just as Well Outside the Office

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Once upon a time, there was a straightforward dress code when it came to your 9-to-5: A suit in gray or navy with a pair of oxfords was always a good bet. Think Mad Men, The Wolf of Wall Street, and Up in the Air. Nowadays, however, with Silicon Valley and start-ups across the nation promoting a laissez-faire attitude—read: normcore—in open-concept offices and boardrooms alike, the prescribed attire isn’t so simple. Enter business casual, and more specifically, business casual shoes.

The term is decidedly tricky. What does business casual actually mean? Here's the CliffsNotes version: business, but not too business, and casual, but not too casual. You still want to present yourself authoritatively, but you also don’t want to be the sole overdresser in the group. The choice of shoes, in particular, is the perfect way to meander between these two points. If you prefer the formality of a suit, pair it with a white sneaker. Similarly, if you’re a jeans-and-tee fella, polish it up with wingtips. There are also styles that fit the business-casual bill by themselves, including desert boots, Chelsea boots, and certain types of loafers.

Need more help getting business casual shoes down pat? Check out the selection below. We work in an office with a ton of stylish guys, and these are the pairs we've tried, tested, and love and wear ourselves. Go forth and conquer with our editors' top 16 picks.

Scout Chukka Boots

Thursday makes a range of business casual shoes, but we're partial to the Scout chukkas. These are perfect for the office—they stay sleek and chic with a suede outer, but the rubber sole keeps 'em nicely casual. Wear them with chinos or dark denim and call it a day.

Original Grand Wingtip Derbies

A wingtip derby is pretty formal shoe, insofar as office-wear goes, at least. But Cole Haan has made it much more casual with the addition of grooved rubber sole. Enjoy the comfort of a casual shoe with the elevated vibe of brogue deets.

Desert Boots

Ah, the desert boot. It doesn't get anymore business casual than this, folks. The shoe is polished, but not too dressy. And Clarks has pretty much got the market covered with its OG version, which is an easy and stylish choice.

Stan Smith Shoes

The white sneaker: Adidas and Stan Smith certainly did it well. Not all offices are chill enough to allow for sneakers, but if yours is, there's absolutely no going wrong with a tried and true classic. If you have a Ludlow suit or something similar hanging around, pair it with this veritable icon.

Greenflex Chukka Boots

Another Chukka boot to keep your eye on is this style from Astorflex, with its low-cut profile and everyday versatility. Come for the durable nubuck leather and crepe soles. Stay for the eye-catching patina that'll only get better with time.

Leather Penny Loafers

A perfect penny loafer that’s at once luxe and durable. You’ll be perfectly fine wearing this into the office, and love it so much, it’ll be a weekend staple, too. Pair with your favorite dress socks for an instantly smart, sharp look.

Larson Weejuns Loafers

Or, for a penny loafer under 200 bucks, G.H. Bass has a classic, timelessly cool option. Whether you wear this with jeans or chinos, you'll look instantly more refined.

The Monterrey Slip-Ons

The guys who make your favorite cowboy boots also make a damn good slip-on shoe. This leather style is a minimalist staple—no fuss, no hassle, and it couldn't be easier to style.

Camden Loafers

If you're not looking to overdo the latter half of "business casual," a penny loafer is your friend. Bonus points if you add a little but of flair by opting for a deep burgundy shade like this one. Wear it jeans and a sports jacket, or tapered slacks and sleek sweater, and you're all set.

Capri Onyx Sneakers

Still yearning for a pair of elevated sneakers? Try these black leather kicks from Koio. They have the sophisticated appeal of a pair of black leather loafers, with the casual, relaxed rubber soles of a pair of everyday sneakers.

Jordaan Leather Loafers

There are very few situations in which a Gucci bit loafer is not the right move. This timeless style is iconic, recognizable, and virtually impossible to mismatch with an outfit. Go ahead and invest—it'll pay dividends.

Tyler Lace Ups

When in doubt, leather boots are a business-casual staple. Black lace-ups are great for wearing with black anything—jeans, chinos, suits, what have you.

Originals 1461 Leather Oxford Shoes

Into white, but really feeling sneakers? The Doc has got you covered with some slightly offbeat oxfords. Pair them with a straight-leg jean and button-up, or a cotton suit, and consider yourself minted.

Epsom Leather Penny Loafers

Like we said, penny loafers are foolproof. And if you're looking for the toniest option, the one beloved by English gents, Grenson's Epsom is what you need.

Camino Penny Loafers

For a more elevated penny loafer, Warfield & Grand has a great option that's under $150. Complete with a burnished look and almond toe, these are elevated, but you can still pair with jeans if you're feeling a bit casual, or chinos to dress 'em up.

Martin Burnished-Leather Loafers

Tom Ford's sleek black loafers are never, ever a bad option. You might think these are straight-up dress shoes, which is fair, but these are cool and stylish enough to go with your favorite straight-leg jeans, a tee, and crisp white socks.

What To Look For

As with most things you're going to wear to the office, you should look for two things when it comes to business casual shoes: comfort and versatility.

The comfort factor is key with any shoe, but especially in shoes that are going to be your go-to style for everything from work to weekends. Whether you prefer a sneaker, a loafer, or a boot, look for materials that you already know you love, like suede, leather, and rubber.

"Business casual" implies that you can dress these shoes up or down, and to do that with ease, pick a style that goes with clothes you already have. Don't buy a new wardrobe based on your shoes; buy shoes that fit in with your wardrobe, both in and out of the office. The more clothes you have that you can wear with these shoes, the more you'll get bang for your buck and actually wear these shoes.

Why You Can Trust Esquire

We’re not going to say something is great unless it’s actually great. Every product in Esquire’s round-ups is carefully curated by our fashion and e-commerce teams.

When it comes to business casual shoes, you can rest assured that we’re hand-selecting styles that we’ve personally tested, tried, and loved, along with styles that the rest of our stylish colleagues here at Esquire endorse for their own wear, both in and out of the office. We’ve had to go through a lot of trial and error, and these shoes are the ones that are simply the best.

Every pick on this list (and our other lists!) comes from years of wearing different things, seeing what we love and what we don’t, and going from there. No two tastes are the same, and no two men are the same. Your proverbial mileage may vary. But if you’re looking for the right place to start, with advice from folks who and care (possibly too much!) about this sort of stuff, this is the place to be.

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