The 20 Best Dress Shoes for Men in 2023, According to Fashion Editors

An Oxford is the OG dress shoe, with a closed lacing for a streamlined silhouette. If you're looking for a dress shoe that feels like a sneaker, Cole Haan's dress shoes have you covered. This option has a hyper-cushioned rubber sole so your feet feel supported.

Urban dwellers can’t just stick with the same pair of old-school dress shoes when having to splash through the dreary, rainy days that lead the change of seasons. Keep your fine Italian loafers in the closet when inclement weather threatens and go for these solid and waterproof leather wingtips. They still boast loads of polish while offering a tough rubber outsole that absorbs the shock of sprinting through downpours in the concrete jungle.

When mixing up your dress shoes, sometimes no laces is the way to go. Monk Strap shoes are secured by a single strap or a double strap and buckle, like these Beckett Simonon shoes. They are traditionally less formal than an oxford shoe, but can still be a dressy option for work.

The best assortment of dress shoes for anyone's closet includes a pair of derbies that you never have to think twice about. While derbies in general are less formal-looking, these cap-toe model are elevated by a cut than the rest, and can work with any kinds of suiting.

The OG loafer, Bass Weejuns has been around since 1936, and its classic penny loafer style still looks great today. Their craftsman-like construction can hold up even after years of wear, and at under $160, it provides incredible value. An easy addition to your weekday uniform.

If your shoe collection is set with a black and brown pair, you can look to expand what dress shoe actually means to you. Getting a sleek pair of boots can work for the right, less formal occasion.

Chukkas were a staple among World War II soldiers and 20th-century polo players. Now they're a menswear essential since they're durable, easy to slip on, and look great with any business casual outfit. These Chukkas look more sleek than rugged, and use the brand’s signature construction to combine sporty comfort with an elegant style. The cushioned moisture-wicking footbed also provides an all-day performance.

Look no further for the perfect starter dress shoes. Bruno Marc makes a pair you can wear at your standing desk and never feel pain, while looking absolutely classic and dress-code-appropriate—all under $60. If you need some everyday dress shoes for the office, these are a no-brainer.

Want something even dressier? These oxfords boast a textured leather upper to ante up your dressy style by a mile and maybe some more. And the Spanish shoemaker’s craftsmanship and heritage in hand-painted patinas justify the price point.

Just because you have to dress up, doesn’t mean you can’t dress easy. Take these slip-on shoes from Clarks, for instance. Their professional facade feels just right with your best office ensemble, or your best business casual chino pants, all while being the easiest to slide into. No dressy appeal is lost here. Instead, more shock-absorbing and moisture-wicking comfort is added.

Venetian loafer is a style you technically shouldn’t dress down with. It’s known for the elegant simplicity of having an upper embellished with nothing but its own flair of velvet or leather. Peter Millar’s performance take in a supple water-resistant suede looks clean-cut enough for the office, but feels sophisticated enough for some fancy dinners, making the pair one of the most versatile dress shoes you can own.

For occasions whose dress code is more relaxing pr up-to-your-own-discretion, dress sneakers can take precedence over loafers, oxfords, or other hardcore dress shoes. Cole Haan’s star has the dressy, brogue-like perforated upper that you’ve always wanted, but the sneaker sole you’d always prefer to walk in every day. And it’s lined to resist against weather too.

Look, you can never go wrong with any Allen Edmond dress shoe, but this cap toe Oxford is especially solid because specifically, it’s a pair of brogues—with a multi-piece build, decorative leather upper, serration along the edges, all that. It is a timeless shape that will last you years. A little bit old-school but definitely purposeful and versatile enough for it all.

We have a rare breed here—a pair of brogue derbies that’s an absolute stunner. From the classic lace-up to the elegant broguing details to the casual derby form to the supple calf suede, these dress shoes boast a handsome design that speaks for themselves. And they go exceptionally well with any color of suiting—navy, grey, black, anything.

Chelsea boots are worth slipping on anywhere, any day. But they come alive the most as dress shoes. Charles Tyrwhitt makes a pair in a traditional heeled profile that still looks modern, in Goodyear welt construction that can last for years, then be repaired or resoled for even more.

The cap-toe is a sleek, timeless option to have in your dress shoe repertoire. It’s defined by a line of stitching that draws a border between the toe from the rest of the shoe. And this comfortable yet premium pair combines that classic shape with a soft leather upper that gets better with age. At this price, it can last you years and decades, from the most formal events to the most business casual hangouts.

Plain toes, on the other hand, have no line of stitching that separates the toe from the rest, and as such don a smooth, seamless look throughout, for the men who prefer a clean, minimalist style for dressing up. And the shine in these BOSS plain-toe oxfords gives the standard silhouette a refined, sleek update.

Considered to be a staple in every man's shoe wardrobe, lace-up shoes are the cornerstone of dress shoes thanks to their timeless appeal and everyday wearability. Plus, these leather wingtip lace-up dress shoes are made with a cushioned footbed and a treaded Vibram® sole that'll ground your every step.

Here’s a pair of plain-toes you can wear to the office, the mall, the bar, the vacation, the dinner—anything where but the gym or your own home. We’re not saying this just because of its balanced dressy-casual appeal. Its waterproof build, breathability, arch support, and all-day comfort cement it as the dress shoes you can walk anywhere in.

Because dress shoes are such a timeless concept, it only takes a bit of futzing with the details to get something new. M.Gemi's loafer has a little leather twist on the front, making them special but not informal.