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
Marco II Monk Strap Shoe
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.
Durable double buckles
Johnston & Murphy
Danridge Double Buckle Monk Dress Shoes
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.”
Premium Leather Slip-On
Premium Leather Oca Low
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
Monolith Brushed Leather Lace-Up 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.
Crockett & Jones
Highbury Plain-Toe Shoe
This upscale option is ideal for people who prefer a traditional style, and it’s a top pick for antiques dealer Cole Myers, who splits his time between Paris and Kansas City, Mo.; the latter is where his shop Myers & Monroe is located. “Good leather shoes are not an arena in which it pays to cut costs,” he says, recommending investing in “the pair of a decade” from this made-in-England favorite. (Crockett & Jones has regal and Hollywood credentials: the brand received a Royal Warrant of Appointment in 2017, and this is the style of dress shoes worn by Daniel Craig’s James Bond). “Even on a budget, one is well served by quality over quantity in the shoe department,” he says. “Polish them a few times a year, and they’ll still turn heads five or 10 years after you bought them.”
Matt & Nat
Itoki Vegan Oxford
For a classic look without leather, this vegan option has clean lines without using any animal products. “They’re timeless and go with everything,” says Nolan Beck-Rivera, a Richmond, Va.-based interior designer and owner of the home goods shop Jolene. He says this pair of lace-up oxfords is “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
Suede Goodyear Welt Derbys
Myers describes Heschung as “a boutique French brand” that’s still under the radar for many American shoppers. Each pair of shoes is handcrafted in the Alsace region and made with a reverse-welt construction where the sole is carefully stitched rather than glued. “There’s an artistic side to wearing shoes that are that beautiful,” he says, adding that “the soles are leather and conceived to be replaced by a cobbler every couple of years.”
Leather chukka boots
Austin Chukka Boots
Dress boots featuring the same body as derby shoes but with a higher rise at the ankle are another favored silhouette of Myers 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.
Wyatt 40 Leather Zip Ankle Boots
“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.
Heeled Chelsea Boots with Pointed Toes
This pair has a similar look to Beck-Rivera’s Saint Laurent favorites and are a smart way to try out the look before investing. “They’re just as stylish and shiny but won’t destroy your bank account,” he says of the block-heeled boots with pointed toes and side zippers.
Thursday Boot Co.
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.
Leather Chelsea boots
Sharpton’s work in the beauty industry means his outfits can push sartorial boundaries, and he “loves footwear with some personality,” especially “shoes that slip on but don’t look like I’ve given up on life.” He calls these boots “amazing” and vouches for their comfort, thanks to the rubber Vibram soles. They’re also available in black, but the white hue is Sharpton’s preferred version since it “adds some attitude” to a look.
Original Achilles Sneaker
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.
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.
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.”
The advice, recommendations or rankings expressed in this article are those of the Buy Side from WSJ editorial team, and have not been reviewed or endorsed by our commercial partners.