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 Boot

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 Derby

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 Boot

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 Boot

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.

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 Sneaker

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 Loafer

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 Up

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.

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.

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.

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.

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