16 Business Casual Shoes for Slightly Dressy Comfort (2024)

A wingtip derby is a pretty formal shoe, as far as office wear goes, at least. But Cole Haan has made it much more casual with the addition of grooved rubber soles. Our experts especially liked this option because you can enjoy the comfort of a laid-back shoe with the elevated vibe of brogue deets. It's the best of both worlds, really.

One buyer said: "Bought these for my husband who often wears a suit and likes to walk home after work. He loves them and said they are his most comfortable shoe. The detailing is fabulous."

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. Plus, they feature a breathable leather lining, lace-up fastening for a secure and custom fit, and our editor's personal favorite, a signature pebble crepe undersole.

One tester said: "I gave these shoes to my husband as a gift to wear with dressed-up chinos. He said they run true to size and are very comfortable. He liked them so much that he bought a second color. He loves the light tan pair."

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. This option not only has a smooth, clean design, but it's also incredibly comfortable and versatile. Our experts recommend that if you have a Ludlow suit or something similar hanging around, pair it with this veritable icon.

One buyer said: "These shoes are very comfortable, and you can wear them for just about any occasion. And with their affordable pricepoint, it's a style that really can't be beat."

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. Our testers noted how this option has more comfort and structure than the standard Chukka boot and compared the wear experience to "walking on a cloud."

One tester said: "These boots easily dress up or down to match the occasion. Design-wise, I like the slightly lower cut to the upper and the lack of a pull loop (which allows pants to fall across the boot more naturally if not cuffed). The natural rubber outsole offers enough traction for casual wear. In profile, it also looks better than some other options. There was a brief break-in period, but the boots have since molded to my feet, and I am comfortable when on my feet all day."

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. Our experts suggest pairing this option with your favorite dress socks for an instantly smart, sharp look. But, because these loafers boast a sleek, minimal design, they also say that you can easily dress them down by wearing them without socks, if you want a more laid-back, cool casual vibe.

One buyer said: "The build quality is top-notch. I bought these around June of 2024 and have been wearing them often. I love the feel of the leather and the overall comfort."

Or, for a penny loafer under 200 bucks, G.H. Bass has a classic, timelessly cool option. Expertly crafted in El Salvador, this style has traditional moc stitching, leather outsoles, and an apron toe. Whether you wear these loafers with jeans or chinos, you'll look instantly more refined.

One tester said: "I love these traditional loafers. I can wear them anywhere with anything. They're a bit stiff at first, but they just want a bit of breaking in, and then they're good to go!"

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. Our testers especially loved these shoes because they come with a wide grooved tongue, which guarantees a secure fit.

One buyer said: "These are a weekly wear, and I love them. They go with just about everything. I got caught in the rain in Mexico and they weren’t affected at all."

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 bit of flair by opting for a deep burgundy shade like this one. Our experts suggest wearing them with jeans and a sports jacket or tapered slacks and a sleek sweater, for a polished, put-together fit.

One buyer said, " I got these to replace my leather sole loafers from another brand that had served me well but were worn through. I am very impressed with the quality and the comfort. Breaking in only took one rough day, and now they are my daily drivers for work."

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 an everyday sneaker. Our testers especially liked how they are made with water-resistant materials, which not only makes them great for travel but also makes them easy to clean.

One buyer said: "These are some of the best sneakers I’ve had in this category of simple design and practical usage. Soft leather inside and out, as well as great craftsmanship, does these sneakers justice. Most certainly a must-have for many occasions to come."

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. When asked why this shoe makes such a great investment, one expert told us that not only do these shoes provide exceptional comfort, durability, and breathability, but the 4-inch heel gives it a touch of elegance for those more formal occasions.

One tester said: "These shoes look even better in person. I wore them basically out of the box to travel for a wedding across country, and they were every bit as comfortable as other more casual options."

When in doubt, leather boots are a business-casual staple. Quiet and unassuming, these boots are handcrafted from full-grain leather and include precision stitches, rawhide leather laces, and rubber insets on leather soles. Our fashion experts noted that black lace-ups are great for wearing with black anything—jeans, chinos, suits, what have you—so you'll want to grab this style while you can (especially now that they're on sale).

One buyer said: "These boots are very comfortable, have high-quality construction, and are super stylish. They are a great option that will serve me well for years to come."

Now available in more shades than ever, the Doc has got you covered with some slightly unconventional oxfords. Built from the brand's traditional, durable smooth leather, our experts recommend pairing them with a straight-leg jean and button-up, or a cotton suit. Congratulations, you can now consider yourself minted.

One tester said: "These Oxfords are a great alternative to the traditional style. They're hardwearing, can be dressed up or down, and have the brand's signature welt stitch that reinforces the shoe. I know a lot of people are nervous to try Dr. Martens due to the myth that they're stiff and uncomfortable, but trust me when I say that once you finally break them in, they'll be the most comfortable shoes you've ever owned."

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. Smart and versatile, this style is handcrafted in a factory in Northamptonshire, UK, from polished black leather and finished with classic apron-stitched seams.

One tester said: "These shoes are perfect for both casual and semi-formal occasions, easily pairing with slacks, jeans, or even shorts. The slip-on design ensures convenience, while the quality leather construction provides comfort and durability. You can't go wrong with this pair."

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 our fashion experts note that you can still pair them with jeans if you're feeling a bit more casual, or chinos to dress 'em up.

One buyer said, " I love my new Camino dress shoes by Warfield and Grand. Not only do they look great, but there was also no break-in time. They were comfortable and fit well from the second I put them on."

Stuart Weitman'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.

One buyer said: "From the moment I slipped them on, it felt like they were custom-made for my feet. The fit was snug without being tight, and there was no discomfort or pressure points that usually come with breaking in new shoes. It was like wearing a pair of well-loved loafers from day one."

What Are Business Casual Shoes?
While this all really depends on the type of environment you work in, for the most part, business casual shoes strike a balance between formal and relaxed styles. The colors typically range from dark hues like brown or black to more versatile shades like burgundy or even sometimes white, but the most important thing to note is you should look for versatile options that can be dressed up or down at your discretion.

What Types of Shoes Are Considered Business Casual?
Business casual shoes can really mean anything—from sneakers to hard-soled dress shoes. As we mentioned above, it really depends on the type of setting you work in, but a great rule of thumb is to look for options that can be paired with things like slacks, khakis, or suit pants. Some other popular options include oxfords, loafers, derby shoes, monk strap shoes, Chelsea boots, chukka boots, and certain dress boots—all of which you will find on this list.

As with most things you wear to the office, you should look for two main things in business casual shoes: comfort and versatility.

Comfort: The comfort factor is key with any shoe, especially in shoes that will 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.

Versatility: "Business casual" implies that you can dress these shoes up or down, and to do that easily, pick a style that goes with the 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.

In addition, here are a couple of other key things to consider:

Material:
Leather: Full-grain leather is durable and ages well, giving a polished look.
Suede: Offers a softer and more casual appearance, suitable for less formal business environments.
Patent Leather: Provides a high-gloss finish for more formal settings.

Construction: As we mentioned above, comfort is key with business casual shoes—especially because you'll be spending over 8 hours in them. You want to look for options that have great arch support but also offer padded insoles and EVA rubber outsoles. At Esquire, one of our number one fashion rules is you shouldn't leave the house in something you feel like you can't wear all day, so you want to make sure your shoes won't cause you any type of pain.

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.