The Best Dress Boots For Men, Selected By Our Editors

Sizes: 6 to 14.5 | Width: Narrow, Regular, Wide | Colors: 3, including Chestnut (shown here) | Special Feature: Rubber Welt Sole

• What’s notable: It’s a sleek boot with hidden comfort features, and it comes in three widths.
• What could be better: It’s on the expensive side.

R.M. Williams boots are worn by stylish, well-traveled men who need a shoe that’s dressy enough for work but still cool and casual enough to wear with jeans. These boots are handcrafted using a single piece of leather at the company’s Adelaide, Australia workshop, and they feature a chisel square toe and Chelsea styling—plus a comfortable rubber sole, cozy insoles and a padded heel lining. The double tugs are also key; they make it fast and easy to get the boots on and off in airport security lines, or when you’re in a hurry.

Sizes: 7 to 16 | Width: Medium | Colors: 2, including Woodbury Dark Roast (shown here) | Special Feature: Waterproof leather material

• What’s notable: They are loaded with comfort features to cushion feet.
• What could be better: Some may not like the look of the thick crepe sole.

Cole Haan reimagined their popular desert boots to make them more comfortable and rugged enough to tackle wet weather. For starters, they traded the traditional stiff crepe soles for a cushioned “FlowerFoam” midsole (FlowerFoam is a lightweight compound that gets its name because it’s partially made from dandelion rubber)—and the layers of cushioning give the boots a bouncy feel. Cole Haan constructed the boots using waterproof leather that’s meticulously sealed to prevent moisture from creeping in, and they added a high-traction outsole and rubber inserts in the heel and toe areas. Even with all of these comfort elements, the boots still feel dressy enough for work and going out at night.

What the reviews say: These boots are comfortable and functional, but reviewers also lauded them for their looks: They’re “light and elegant, a pleasure to wear them all day,” says a customer.

Sizes: 7 to 15 | Width: Medium | Colors: 4, including Tan (shown here) | Special Feature: Ergonomic footbed

• What’s notable: They are handcrafted using premium leather, and they are reasonably priced for such a high-quality boot.
• What could be better: The boots only come in full sizes—if you’re in between sizes, the company suggests sizing down.

Handmade in a Northern Italian workshop by a family that’s been crafting high-quality boots for six generations, these boots represent everything a good Chelsea boot should be: They are made from soft leather, have elastic inserts and are easy to put on and pull off. What’s more, they also have an ergonomic footbed and a soft crepe sole for comfort. Astorflex uses environmentally friendly construction, so these boots are kind to both your feet and the planet. 

What the reviews say: Customers love the versatility of these boots: “I wear them to work, on the weekends, and to church,” says one reviewer. Another commented how “slipping [them] on and off in the airports” makes them a good choice for travel. And several reviewers praised the boots for their comfort. “Super comfy out of the box,” sums up one reviewer.

Sizes: 7 to 14 | Width: Medium | Colors: 5, including Black (shown here) | Special feature: Vachetta leather lining that controls temperature and odor

• What’s notable: They are expertly crafted, polished, and very comfortable plus supportive.
• What could be better: Slim in the ankle, they might feel snug on guys with larger legs.

Beckett Simonon shoes are made to order in small batches in their workshop in Columbia, and shipped directly to consumers, which cuts out the middle man and keeps prices reasonable. The company also uses leather from a LWG Gold Rated tannery. These handcrafted equestrian-inspired boots are a perfect example of high-quality craftsmanship. Made of full-grain leather, the boots offer excellent arch support, a roomy almond-shaped toe box that won’t pinch toes and a Vachetta leather lining that controls temperature and odor. They have rubber heel caps for extra traction and a steel shank sandwiched between the insole and outsole for support. A carnauba wax and shea butter finish provides rich color and a hint of luster.

What the reviews say: Several customers reported that they get compliments on these boots whenever they wear them, and reviewers rave about the excellent craftsmanship. “The boots look beautiful and feel great on my feet—outstanding value and construction,” says one. “These are high quality, fit great, are very comfortable and look fantastic,” echoes another. 

Sizes: European sizes 40 to 46 | Width: Medium | Colors: 1 (but they are also available in taupe suede)| Special Feature: Pull-on tabs

• What’s notable: These boots are edgy and fashionable and have a comfortable rubber sole.
• What could be better: They are very expensive.

Think of these as a more polished and grown-up version of a combat boot. Edgy but still buttoned up enough for work, they are handcrafted in Italy from full-grain leather, have comfortable, flexible rubber soles that don’t look clunky and they have pull tabs which makes them easy to get on and off. If you prefer a slightly more casual look, opt for the taupe brown suede version.

Sizes: 4 to 14 | Width: Medium (but they run wide) | Colors: 8, including Brown (shown here): Special feature: TPU outsole

• What’s notable: They are waterproof and have a rugged sole.
• What could be better:  These boots aren’t as dressy as some of the others on this list.

These iconic boots are immensely popular for a few key reasons: They are made of premium water-resistant leather and have a durable Thermoplastic Polyurethane (TPU) outsole, a cushioned midsole, a SPS Max Comfort system for shock absorption and a removable comfort footbed (plus an extra set of footbeds). Blundstones are rugged enough to wear in snowy and rainy conditions (the tread offers excellent traction and prevents slipping), yet still look professional enough to wear to the office. 

What the reviews say: Customers note that these boots take a few weeks to break in, but after that, it’s smooth sailing (or at least walking.) “Now, my boots fit like a glove and I wear them practically every day,” says a reviewer. Another reviewer says: “[They] are ultra comfy, and they go with pretty much any outfit.”

Sizes: 8.5 to 13| Width: Medium | Colors: 2, including Black Full Grain (shown here)| Special Feature: Memory foam insole

• What’s notable: These boots are reasonably priced and look as stylish as more expensive options.
• What could be better: Some people find the fit a little off.

At $129, these aren’t necessarily cheap, but they are well-priced for high-quality leather dress boots. Made in Brazil, they have a hidden side zip for a sleek, refined look, and a removable memory foam insole keeps feet comfortable. The tread has been updated to be quieter and smoother to walk in (no clanking across the floor), and the style is dressy enough for any occasion.

What the reviews say: A few customers struggled with the fit, but overall reviews are extremely positive. “These boots fit perfectly and are very comfortable out of the box. They look great, too,” comments a reviewer. Another says, “[They] are very comfortable for walking around the office.” A reviewer who works as an airline pilot says, “This boot feels like I am wearing a slipper. If you are [looking] for a stylish boot that you can wear for hours on end look no further.”

Sizes: 5 to 16 | Width: AAAA to EEE | Colors: 5, including Dark Chili Leather (show here)| Special Feature: CustomCork insoles 

• What’s notable: These are impeccably constructed in the US (in Port Washington, Wisconsin) and the traditional style is appropriate for buttoned-up environments. Plus, they come in a wide range of widths.
• What could be better: While the custom insoles provide comfort, these boots aren’t going to feel as cushy as some other shoes on this list.

This dress boot is a spin-off of Allen Edmonds’ popular Park Avenue Oxford, which was first introduced back in 1982. The boot has the polish of the Oxford thanks to the sturdy bench-welt construction, classic cap-toe shape and single-layer, vegetable-tanned leather soles. Made of calfskin leather, these boots may look stiff, but the brand’s CustomCork insoles mold to your foot and keep the boot feeling comfortable as you walk across the office—or town.

Sizes: 7 to 15 | Width: Medium| Colors: 10, including Cola Suede (shown here)| Special Feature: Pebble crepe rubber outsole

• What’s notable: The paired-down look is simple and chic.
• What could be better: Some may not care for the Clarks Originals fobs threaded through the laces.

As the story goes, Nathan Clark, great-grandson of Clarks founder James Clark, came home from serving on the staff of the West African Brigade in Burma and India during WWII with an idea for a new shoe. He had seen officers wearing suede boots with crepe soles that were made at the bazaar in Cairo— and was instantly inspired. Clarks Desert Boots weren’t available in the US until 1950, but they’ve been selling like gangbusters ever since. These iconic lace-up boots are a version of a Chukka boot, with two eyelets on each side, a pebble crepe rubber outsole and a comfortable and versatile ankle height.  

What the reviews say: A couple of reviewers claimed the Cola Suede color was not exactly the same shade that was pictured. But overall, viewers are fans of these old-school boots and have been buying them for years: “[They’re] comfortable, stylish and despite their simple appearance, rugged and long-lasting,” says one reviewer. Another was impressed by the fact that you can literally wear them everywhere: “I actually got them for a funeral.”