Most Comfortable Men’s Dress Shoes 2025

Sizes: 7 to 15 | Widths: Standard, wide | Colors: 13 total, including Honey and Obsidian | Upper material: Full-grain leather | Sole material: Rubber

• What’s notable: A perforated calfskin lining encourages airflow to keep your foot cool. 
• What could be better: These shoes are on the heavier side.

The Amberjack Original earns the top spot on our list, thanks to its host of comfort-enhancing features: The shoes are designed with heat-activated arch support that molds to your foot, along with a perforated calfskin liner that increases airflow. “These surprised me,” says Flood. “I didn’t think I would be the biggest fan but I like the silhouette of the shoe and it’s very easy to dress it up and down.” The Original has a full-grain leather or suede upper (sourced from Leather Working Group tanneries) that feels broken-in straight out of the box, and a grippy rubber outsole provides excellent traction on multiple surfaces. Flood mentions that he struggled to keep his heel locked in the shoe without tying it really tight, but that the heel is “very comfy” otherwise. There are 13 shades to pick from, and a wide option for those who need the extra room.

Sizes: 5 to 16 | Widths: AAAA to EEE | Colors: 9 total, including Black and Walnut | Upper material: Calfskin | Sole material: Leather

• What’s notable: There are 10 different width options, making this shoe suitable for many foot types. 
• What could be better: The leather upper requires a bit of time to break in at first.

Wisconsin-based Allen Edmonds uses premium European calfskin leather to craft the Park Avenue Cap Toe Oxford—a crowd favorite since 1982—and that quality is apparent right off the bat. “You can tell these things are made well,” says Flood. The soles are made of a single layer of vegetable tanned leather, with a rubberized heel for extra traction. You’ll also find the brand’s signature CustomCork insole inside each shoe for molded support. Flood notes that the shoes fit true to size—and since there are 10 width options to pick from, you can get a fine-tuned fit. He also notes that the leather material “does require some break-in time,” so keep this in mind if you’re planning on wearing these shoes to a specific event.

Sizes: 8 to 15 | Widths: Medium | Colors: 2 total, including Gale Grey and Navy | Upper material: Textile | Sole material: Rubber

• What’s notable: A breathable textile upper keeps feet ventilated and cool.
• What could be better: The Gale Grey shade easily shows dirt and markings.

If you’re in the market for a slightly more casual dress shoe, the Peter Millar Drift V2 offers plenty of comfort, courtesy of a breathable textile upper in lieu of leather. “The uppers remind me of Nike Flyknit material, making them easy to put on and fit well to your foot,” Flood says. These shoes are designed to slip on with a set of elastic laces that don’t require any tying, although conventional laces are included if you prefer them. Flood also mentions that the lightweight, three-part sole “has a good amount of squish,” and that the shoe is solidly constructed despite its lack of traditional leather elements. After wearing these shoes for a few weeks, Flood reports that they’ve held up well. Just keep in mind: Scuffs and dirt will show up more easily on the Gale Grey color than the Navy hue. 

Sizes: 6.5 to 16 | Widths: Medium, wide | Colors: 18 total, including British Tan/Ivory and Black Leather/White | Upper material: Leather, textile | Sole material: Rubber

• What’s notable: These shoes have a sneaker-like, flexible sole that makes them comfortable enough for all-day wear.
• What could be better: The lighter-colored soles are more likely to gain scuff marks than dark ones.  

For those who spend long periods of time on their feet, the Cole Haan ØriginalGrand Wingtip Oxford is a smart choice. The ultra-light, flexible outsole won’t weigh down your foot, while the cushy EVA midsole adds an extra layer of support. “They’re a good everyday dressier work shoe option, especially if you stand for long periods of time,” says Flood. The uppers are made of premium, Leather Working Group-sourced leather. After testing them out for a few weeks, Flood’s one concern with these shoes is their longevity: “Since they’re so light, the sole might wear quickly,” he says.

Sizes: 8 to 13 | Widths: Medium | Colors: 3 total, including Pebble and Chestnut | Upper material: Suede | Sole material: Leather and rubber

• What’s notable: The water-resistant suede uppers pair with the light EVA outsole to create a shoe that’s durable enough for outdoor environments.
• What could be better: The color selection is limited, and there are no wide options available.

The Peter Millar Excursionist Penny Loafer is our top suede pick on our list of the best loafers for men; if the occasion allows, this style serves as a smart dress shoe. “These penny loafers are a great warm weather or summer option,” says Flood. While the water-resistant suede upper reads a bit less formal than traditional leather, the sharp, tailored details lend an air of easy sophistication. The lightweight EVA outsoles provide all-day comfort, while a textured bottom ensures good traction on a variety of surfaces. Additionally, Flood appreciates the convenience of slipping these loafers on and off without having to tie them.

Sizes: 7 to 14 | Widths: Medium (D), wide (3E) | Colors: 3 total, including Gray and Navy | Upper material: Nubuck leather | Sole material: Rubber

• What’s notable: This Oxford shoe from Florsheim has a perforated upper that boosts ventilation. 
• What could be better: It has a wider-than-average toe box, so it can be easy to order one size too large.

The Oxford is a classic type of lace-up dress shoe, and this version from Florsheim earns extra points for its perforated nubuck leather upper that increases airflow and a neoprene lining that wicks away excess moisture. “I like the breathability of the Frenzi,” says Flood. The high-rebound EVA sole is similar to ones found on athletic shoes, providing plenty of cushioned support. Flood notes that the the toe box is a little wider than some of the other options he tested, which may make finding your correct size a bit less straightforward.

Sizes: 6 to 15 | Widths: Medium | Colors: 6 total, including Maple and Black | Upper material: Calfskin leather | Sole material: Rubber

• What’s notable: This dress shoe-sneaker hybrid has a removable memory foam footbed.
• What could be better: The contrasting white outsole may read too casual for formal events.

On days when you need to look sharp and cover some distance on foot, the Wolf & Shepherd Crossover Longwing Hybrid is an excellent choice. The full-grain Italian calfskin leather upper is paired with a sneaker-like TPU (thermoplastic polyurethane) sole that offers great traction over uneven surfaces. “These were the most comfortable of all the shoes I tested,” says Flood. “The sole is firm with some give to it, but what surprised me most is how plush and breathable the inside is for it being a leather shoe.” While these shoes only come in one width, the memory foam insoles are removable and come in wide and narrow options. 

Sizes: 7 to 14 | Widths: Medium | Colors: 5 total, including Black and Tan | Upper material: Full-grain leather | Sole material: Leather, rubber

• What’s notable: These Oxfords have a tapered footbed that enhances arch support. 
• What could be better: The leather, while high-quality, has a bit of a break-in period.

While some of the styles on our list skew more business casual, the Beckett Simonon Dean Oxford is truly a dress shoe in every sense of the word. With a full-grain leather upper, almond-shaped toe box and tapered footbed for optimal arch support, it excels in both sophisticated style and ergonomic comfort. “These shoes fit perfectly and are my favorite shoe out of all the options I tested,” says Flood. He notes that they feel solid and have the “best construction” out of all the shoes he tried—courtesy of a steel shank riveted to the insole and outsole that provides extra balance and support. 

Sizes: 7 to 15 | Widths: Medium | Colors: 5 total, including Stone and Dark Chestnut | Upper material: Leather, nubuck | Sole material: Rubber

• What’s notable: The natural crepe rubber sole found on this Chelsea boot is eco-friendly.
• What could be better: The crepe rubber soles wear down more quickly than synthetic rubber soles, especially if worn frequently on rough surfaces.

The Astorflex Bitflex is featured on our roundup of the best dress boots for men as our pick for the best Chelsea dress boots. Each pair is handmade in Northern Italy by a family that’s been making boots for six generations, and the attention to detail is immediately apparent upon first wear. When Flood put them to the test, he was impressed with how seamlessly they fit into his wardrobe. “I’ve been grabbing this dress boot over and over as a daily option,” he says. “The crepe sole is extremely comfortable and the boot has almost no break-in period.” Plus, the boot features a crepe rubber outsole that’s more eco-friendly than synthetic rubber options. Choose from leather or nubuck uppers in rich, versatile shades; just keep in mind that nubuck is softer and requires more maintenance than leather.

Sizes: 8 to 14 | Widths: Medium (D) | Colors: 3 total, including Tan and Black | Upper material: Full grain leather | Sole material: Leather and rubber

• What’s notable: These shoes have memory foam insoles that make them comfortable for long periods of time.
• What could be better: At this price point, the leather quality is lower than the other options on our list.

The Johnston & Murphy Lewis Plain Toe is a great option for those who don’t mind swapping premium leather for an affordable price tag. Like some of its more expensive counterparts, it has a cushioned memory foam insole and a grippy rubber outsole. You won’t find many ergonomic features like a perforated upper or EVA midsole, but if these aren’t a priority to you, then we recommend this pick. “It’s not the flashiest shoe, but it’s straightforward and gets the job done,” says Flood. He mentions that the leather is of lower quality than the other picks on this list, but that it’s fair considering the price.