The 16 Best Dress Shoes for Men, According to Style Experts

You’ve probably noticed a steady relaxation of dress codes over the past several years, yet there are still many situations and social obligations that necessitate  slipping out of slippers and into some elevated footwear. Whether this arises from a professional obligation or a festive invite, one thing’s for certain: Shoes are required.

We asked professional stylists and fashion insiders for the lace-ups, boots and sneakers they wear and suggest to clients for dressed-up occasions. These are the pairs they recommend.

Traditional monk straps

Versatility is the No. 1 factor Huntington Beach, Calif.-based Jim O’Brien, co-founder of Cleobella, considers with his formal shoes. He likes that this single monk strap style “can be dressed up or down” for different events, from weddings to dinners out. They’re “super comfortable as well, especially for a stiffer shoe,” he adds.

Sleek sneakers

The key to dressed-up sneakers is finding a leather pair free of busy accents or logos. The style is “acceptable to wear with dress clothes,” confirms Los Angeles-based personal stylist Rayne Parvis, who advises people to wear these sneakers in place of brown lace-up dress shoes. Clients have told her this pair is “super comfortable” and can be made even better for dancing the night away if you “remove the insert cushioning and put your own orthotics in.”

Durable double buckles

These double-strap shoes have the same antiqued leather treatment that O’Brien prefers, with darker dye deposits at the toe and heel (the spots where a shoe would naturally begin showing its age first), offering more durability. “I love the variation in color from light to dark,” he says, adding that the mixture of light and dark brown makes them “great for all occasions.”

Business casual

Brazilian brand Cariuma’s collection includes a variety of stylish leather lace-up and slip-on sneakers. If you’re looking for a dressed-up pair of kicks to pair with jeans and a blazer, consider either of these pebbled pairs, which come in brown, black and white. They also feature memory foam insoles for comfort and non-slip rubber soles.

Bold derby shoes

“I love a classic shoe with a twist,” says Wes Sharpton, lead brand educator and stylist at Hairstory, who splits his time between Catskill, N.Y. and New York City. He calls this leather lug sole style “visually intriguing without being in your face” and likes the extra height the 1.75-inch rubber soles add.

Waterproof lug soles

This under-$100 find from a popular brand known for comfort has a lug sole that’s slightly subtler than others. The laces and classic body shape are characteristic of traditional men’s dress shoes, while the rugged rubber soles still make a statement with any formal outfit.

Vegan minimalist

For a classic look without leather, this vegan pair has clean lines without using any animal products. Nolan Beck-Rivera, a Richmond, Va.-based interior designer and owner of the home goods shop Jolene, praises Matt & Nat’s footwear, noting that his favorite shoes from the brand are “timeless and go with everything”. His similar lace-up oxfords are “comfortable” and “wonderful because no animals were harmed in their making.” The Montreal-based brand is popular for using a range of earth-friendly materials like the biodegradable polyurethane used here.

Craftsmanship in suede

Mix up the classic leather look with a pair of suede dress shoes, such as this pair from Gordon Rush. The wingtip derby-style features decorative perforations, known as ​​broguing, that add subtle flair to a suit or other formal attire. They come in neutral tan, as well as navy with contrast stitching.

Leather chukka boots

Dress boots featuring the same body as derby shoes but with a higher rise at the ankle are another favored silhouette of antiques dealer Cole Myers, who splits his time between Paris and Kansas City, Mo., and one that he regularly gets compliments on. He says wearing a pair is “a hack” for looking “remarkable even if you’ve just thrown something on and darted out the door.” This pair features leather uppers for a sleek look with cushioned insoles for comfort.

Heeled style

“One of my clients refers to me as ‘Boots’,” Beck-Rivera explains regarding his devotion to this designer pair. “They make me feel like Johnny Cash, and I’ve almost walked the soles off them.” The almond toe and smooth black leather are both characteristics of traditionally formal footwear, while the stacked heel adds a rockstar vibe. Plus an interior zipper makes slipping them on and off easy.

Classic Chelsea boot

If you’re looking for a boot that you can dress up for the office or evenings out, a classic Chelsea style is a smart pick. This Nisolo pair is a Buy Side favorite; the boots are made with water-resistant leather (a suede option is also available if you’re not as concerned with rain and snow) and have slip-resistant rubber soles. For a sleek, monochromatic look, try this Blundstone pair, which features rubber soles and water-resistant leather uppers. Consider our list of the best winter boots for men for more options.

Versatile boots

O’Brien counts this pair as his “super versatile, daily go-to” for years, wearing them for more dressed-up occasions and with casual daytime outfits. They’re “durable work boots” in a pinch, too, thanks to rubber outsoles, steel shank construction and treated leather that’s intended to look better as it ages. They come in 13 colors and finishes, and the style can easily be adapted for different wardrobing needs. O’Brien’s matte black pick is one of the more formal options, while hues like the Dark Charcoal and Olive would pair easily with casual clothing.

Dressed-up sandals

For formal occasions with a looser dress code, like beachside celebrations or a stepped-up backyard soiree, a woven slide is a solid option. “I picked up a handmade pair of huaraches in Mexico last summer when I was there for a wedding, and they became my go-to footwear for events of all formalities for the rest of the season,” says Beck-Rivera. He likes this “lovely tobacco color” from Nisolo for wearing with creamy linen or other light-colored clothing.

Luxe lace-ups

Parvis says this “leveled-up sneaker” is a favorite with her fellow stylists and clients, calling it “understated and dapper.” In lieu of a logo, there’s a string of numbers on the side of the leather low-tops that Parvis calls “the equivalent of Christian Louboutin’s red bottoms.” In other words, if you know, you know.