Best Business Casual Shoes for Men

Are you stepping out into the world but unsure what to step out in? When it comes to menswear, business casual sneakers for men are king, although there are a few versatile sneakers for men that can serve double-duty. From heel to toe, your shoes can make a powerful first impression, show off your personality, and carry you comfortably from point A to point B. 

So, what are the best business casual shoes for men looking to check every box when it comes to the different types of dress shoes?

We’ve found seven unparalleled pairs that will look right for nearly any occasion. If you’re curious about stepping up your shoe game, revitalizing your closet, or finding comfortable dress shoes to take your wardrobe from “just fine” to “professional perfection,” read on.  

#1 Oxfords

First popularized by the students at Oxford University, the Oxford is thought of as a timeless leather shoe, known for its close lacing, low heel, and exposed ankle, deriving much of its style from popular boot trends of the 19th century.

Don’t mistake these U.K.-born shoes as strictly formal, though. You can dress your Oxford shoe up or down, looking just as good with a full suit as they do with a pair of chinos. No wardrobe is complete without a oxford shoe pair; in fact, the avid shoe completionist will have a few different pairs in rotation at any given time.

Because of the variety of Oxford styles, there’s no reason not to add a few to your collection. Consider some of the following variations on this classic business casual shoe:

  • Plain-toe – Plain doesn’t indicate a lack of smart-stylings, only that this is the most reserved and formal choice when it comes to a pair of Oxfords. With no cap, minimal detailing, and usually in darker tones, the plain-toe Oxfords are sophisticated enough for a wedding and sharp enough for an evening out on the town.
  • Cap-toe – The simple stitch line at the front of the shoe sets the cap-toe Oxford apart from its more formal companion. Cap-toes look perfectly appropriate at an office or a smart-casual function. You can even find yourself a perfect pair for everyday wear.
  • Wingtips – Wingtip Oxfords have more detailing and stylistic flair than the streamlined cap-toe shoe. A W-shaped (or wing-shaped) overlay extends the cap-toe stitching along the sides of the shoe and often features a line of decorative perforations, also known as “brogue” detailing.
  • Saddle – This classic two-toned dress shoe was popularized by school uniforms and 1950s preppy stylings. These shoes offer a bold look while retaining a little of their business-casual formality.

As far as versatile style goes, Oxfords are a top contender. With plenty of colors and variations to choose from, you can find a pair to complement nearly every outfit, without sacrificing comfort either.

#2 Derby Shoes

Curious about how to lace dress shoes? The average shoe-wearer might have a difficult time distinguishing between a derby shoe and an Oxford. As the footwear aficionado knows, it mostly comes down to the laces.

Where Oxfords are known for their close-laced design, derby shoes feature an opening lacing style and a slightly roomier fit. 

If you’re considering adding a derby shoe to your collection, consider these key details:

  • Comfort – Bigger feet may find the larger in-step of derby shoes to be a welcome design choice. Whether your arches are a little bit higher or your feet are just a tad wider, a pair of derby shoes might keep you on your feet for longer and with less pain, so you never have to suffer in the name of style.
  • Rounded toe – The silhouette of a derby shoe is often noted for its less formal qualities, due to the rounded toe common in its design. If you’re looking for a more casual shoe that still feels classic, the derby can be a sensible choice.

#3 Chukka Boots

With their versatility and military-inspired style, chukka boots offer a durable choice for a multiseason, business casual shoe.

Frequently, chukka boots are styled in suede or leather, with grippy soles designed to withstand difficult terrain while remaining comfortable and stylish. Men's boots are understated, ankle-high, and usually only feature three or four eyelets.

When determining if chukka boots are right for your wardrobe, consider the following:

  • Indoor vs. outdoor use – Are you commuting on foot, riding the train, or taking your dog for a walk every morning? For those that do a little more walking, these comfortable, rugged business casual shoes can stand up to the elements while still retaining a fashionable look.
  • Colorful simplicity – While chukka boots are typically minimalist in design, featuring few stitching details or embellishments, they do frequently come in a variety of interesting and complementary colors. Choose between wine red, dark blue, or a variation of creamy browns to bring a unique hue to your wardrobe.

#4 Leather Sneakers

While sartorialists of yesterday may have scoffed at wearing sneakers outside of the gym, a contemporary wardrobe wouldn’t be complete without subtle, simple leather sneakers for men that are just formal enough for the modern office.

When looking for leather sneakers that can live up to the title of the best men’s business casual shoes, you’re typically deciding between monochrome options like:

  • Classic white – White sneakers aren’t just for the tennis courts. For years, white sneakers have maintained their place as a smart and understated option to pair with a business casual wardrobe. White sneakers pair best in the summer with pastels and linens, but they can also hold their own as part of any winter ensemble.
  • Essential black – Clean, quiet, and elegant, black leather sneakers can offer pillowy-soft comfort while keeping a tasteful shape and silhouette. 

The business casual leather sneaker is typically a low-top with just enough sophistication to hold up against any dress shoe. Plus, they can take a beating better than most Oxfords or derby shoes.

#5 Chelsea Boots

Dating back to the mid-1800s and the reign of Queen Victoria, Chelsea boots were a revolutionary unisex design fit for royalty. Over 100 years later, the boots were made famous by British rockers, American celebrities, and a generation of ‘60s fashion icons. 

The slick design and lack of laces make for an edgy silhouette that’s instantly recognizable all over the world. Chelsea boots continue to turn heads whether they’re paired with a suit, a pair of jeans, or a rumbling motorcycle.

If you’re curious about adding Chelsea boots to your repertoire, consider the factors that make these boots so iconic:

  • They fit like a glove – Snug but not too tight, Chelsea boots are designed to conform to your foot and create a sleek profile. Because of the lack of laces, Chelseas are manufactured with stretchable elastic material near the ankle and pull tabs on the back for easing them on and off—no relacing and tying necessary.
  • They’re a flattering ankle height – The Chelsea boot was created with horseback riding in mind, therefore offering a little more protection than your average dress shoe. The ankle height that shielded 19th-century riders still makes for a great defense against rain puddles, mud, and other potential hazards.
  • They feature low heels – Chelseas can add a bit of height and a lot of style to any outfit thanks to their heels. Often, the heels are higher than that of traditional dress shoes without being particularly pronounced, so you can enjoy a subtle bit of lift.

#6 Loafers

A slip-on option with plenty of variety, tons of styling options, and even the possibility for sockless comfort, loafers are an enduring footwear option not to be forgotten. 

While loafers don’t typically fit into a black-tie event, they can be worn just about anywhere else—even with a pair of shorts in the summertime. To make things a little more complicated (or more fun, depending on how you look at it), there are more variations of loafer than nearly any other kind of business-casual shoe.

When exploring loafers, consider options like:

  • Tassel – Easily distinguished by their namesake tassel, these loafers are a semi-formal option with some old-school charm. Often designed in suede and considered part of a spring or fall wardrobe, tassel loafers can make a fashion statement while remaining subdued.
  • Kiltie – Kilts aren’t just for the Scottish. These loafers are distinguished by their fringed design and are usually offered in black and brown leather for the fall and winter seasons.
  • Penny – While you may choose to keep your loose change elsewhere, there’s no denying the timeless look of penny loafers, complete with a horizontal strap, deep colors, and slotted detailing.

#7 Monk Straps

The name might recall monasteries of the 15th century, but monk straps are a present-day favorite among menswear enthusiasts. 

Not only do monk strap shoes strike a perfect balance between Oxfords and derbies—in terms of formality—but they also feature a striking look that stands out from the crowd without looking ostentatious.

Monk straps typically come in leather and are offered in two distinct design styles:

  • Single strap – Crisp and sophisticated, the single monk strap is typically thought of as the more formal variation. A wide strap crosses the width of the foot and connects to a single buckle.
  • Double strap – Much the same as the single version but with a little more hardware, the double monk strap is outfitted with two buckles and may feel a bit more ornate, elaborate, and decorative.

Build a Brilliant Wardrobe with Toms

There may be more to business casual shoes than meets the eye, but at the very least, you should be more prepared to take the next step forward. While you’re weighing your options and asking if the shoe fits, there’s one place to check out for all your business casual footwear needs.


At TOMS, we offer more than classic stylings. From slip-ons to boots, we’re reinventing shoe design and redefining comfort with our OrthoLite® insoles. 


Reviewed By Dan Caves

Dan Caves is the Senior Manager of Digital Marketing at TOMS and has been operating in the digital space for 6 years, writing about the latest trends or styles and helping brands make bold statements with innovative tactics and creative concepts. He's determined to go all the places, see all the things, and pet all the dogs.