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Updated Mar 06, 202512 Most Comfortable Dress Shoes For Men To Wear To Weddings
Form meets function in our menswear expert's dozen faves
Photos, left to right: Cole Haan, Nordstrom Rack, Rockport
Nothing kills the vibe of a great wedding or reception like uncomfortable footwear. You've got to be ready when the DJ plays your song so comfortable dress shoes for men are an absolute wedding essential. Before you grimace, let me assure you that it is indeed possible to look your best for the occasion without sacrificing comfort. The market is teeming with everything from oxfords to slip-ons that offer great support and sneaker-level tech without a clunky, orthopedic look. If you're looking to wear your dress shoes through the end of the night (or well into the morning) and not be nursing shin splints, these are some of the best options around.
In this article:
The Most Comfortable Dress Shoes for Men
The right dress shoe depends on what you're looking for in terms of comfort and style. For you that might mean a dress shoe that can be quickly broken in or one that doesn't need breaking in at all and feels like you've been wearing it for years right out of the box. Other desirable features may include orthopedic soles and extra padding for greater support. Read on for some of our favorites.
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The Best of Both Worlds: Amberjack The Original
Photo: Amberjack
Amberjack specializes in dress shoes that don't skimp on comfort, like the Original style. Available in a wide range of colors, it pairs well with just about any suit and has heat-activated arch support (perfect for when you're tearing up the dance floor at the reception).
The One That Feels Like a Sneaker: Cole Haan 2.ZEROGRAND Laser Wingtip Oxford
Photo: Cole Haan
Cole Haan is under the Nike umbrella, so it's no surprise that they've made a men's dress shoe that feels more like a sneaker. Featuring all of the slick tech and support you'd expect from an athletic shoe in a fashion-forward, suit-ready silhouette, it's a comfy menswear flex for the sartorially bold.
The Loafer You Don't Need to Break In: Myrqvist Mölle
Photo: Myrqvist
Loafers are notoriously tough dress shoes to break in, often requiring any number of home remedies before they're wearable for more than an hour at a time (I'm partial to bunching a couple of pairs of socks into mine). Myrqvist's Mölle tassel loafer is the only pair I've ever been able to wear straight out of the box and they feature soft leather and construction that's sturdy without being constricting.
The Best Bargain: Dr. Scholl's Sync Oxford
Photo: DSW
Dr. Scholl's has long been synonymous with orthopedic inserts and shoes with top-notch support. At under $100, their dress shoes are also one of the best bargains out there.
The Best Comfortable White Dress Shoe: Dr. Martens 1461 Iced Derby
Photo: Nordstrom Rack
You may associate Doc Martens with hipsters and the punk kids you went to high school with, but make no mistake, they're more than just stiff-as-a-board boots. Their entire line is renowned for its orthopedic support (even their boots, once you break them in) and some of their dress shoes can bring an edge to a wedding suit. Take these 1461s in white leather, which are equal parts sartorial swerve and unbeatable comfort.
The Best Slip-On: Florsheim Motion Moc Toe
Photo: Zappos
Florsheim's slip-on moc toe is designed to merge the style of a loafer with the comfort of a house shoe or sneaker. It's loaded with a signature COMFORTECH sole and features a soft leather construction that requires no breaking in to fit and feel great.
The Best Wingtip: Dr. Comfort Men's Wingtip
Photo: Dr. Comfort
Those in search of a wingtip oxford that offers maximum comfort need look no further. The appropriately named Dr. Comfort's features a full-grain leather construction with a roomy toe box and a padded heel.
The Dress Shoe You Won't Have To Break In: Beckett Simonon Dean Oxford
Photo: Beckett Simonon
Beckett Simonon is a favorite shoe brand here at The Knot for their handmade construction and transparency on workplace practices and employee benefits. Their shoes are already some of the best for getting dressed for a wedding, but the unique construction of their signature Dean oxford also makes it one of the easiest dress shoes to break in by utilizing a Blake stitch construction that makes for a far more flexible shoe.
The Most Comfortable Tuxedo Shoe: Ace Marks Carlo
Photo: Ace Marks
Ace Marks has the most comfortable tuxedo shoe on the market these days in their Carlo style. Made from wholecut patent leather, it's a stunner of a shoe that also happens to feature inserts for extra cushioning. Go ahead and write the long version of your vows–if you're wearing these, you won't mind standing at the altar a little bit longer.
The Most Comfortable Brown Dress Shoe: ECCO Cityray Perforated Toe
Photo: Zappos
You may recognize ECCO as one of the most popular brands in hospitals for medical professionals who have to spend upwards of 12 hours on their feet. As it turns out, they can make a pretty great dress shoe, too. The Cityray comes with all of the comfort tech you'd expect from ECCO, plus a perforated construction that makes the shoe both breathable and flexible.
The Softest Penny Loafer: Nordstrom Black Driving Loafer
Photo: Nordstrom
These loafers from Nordstrom blend the style and silhouette of a classic penny loafer with a soft, broken-in construction. The shoe's driver sole also adds to the comfort, making for a loafer that won't leave you sore.
The Best Waterproof Comfy Dress Shoe: Rockport Taylor Cap Toe Oxford
Photo: Rockport
With Rockport's signature truTech sport technology in the sole, their cap toe Taylor oxford is among the best comfortable dress shoes out there. It also features waterproof materials and seam-sealing, which will help grooms and guests alike stay dry in the instance of a little bit of rain the day of a wedding.
Where to Buy Comfortable Dress Shoes for Men
Finding comfortable men's dress shoes has never been easier. These days there are a ton of brands that specialize in fusing fashion with function by engineering classic dress shoes with excellent support. Here are some of the best places to pick up a pair for yourself, no matter your style or budget:
Amberjack: NFL superstar Aaron Rodgers recently invested in this upstart brand that aims to make semi-formal and formal dress shoes with support that lasts throughout the day and night. Their designs are stylish, modern, available in standard and wide sizing and range in price from $175 to $199.
Rockport: Rockport's orthopedic support is tough to beat and the brand is also a go-to source for dress shoes that can hold up to the elements thanks to their many waterproof styles. Available in both wide and standard sizes, Rockports tend to clock in around (and sometimes under) $100.
Florsheim: Loafers are notoriously difficult to break in but with Florsheim, you needn't worry. All of the brand's offerings prioritize comfort, but it's the loafers that stand out. Boasting cushy soles and soft leather construction that doesn't actually require breaking in, they're comfy from the moment you slip them on. Not every style is available in wide fit but they are sized as large as 16 and generally priced between $130 and $140.
Dr Martens: Doc Martens might not strike you as the most traditional dress shoe, but a pair of their oxfords can lend a fashion-forward edge to a wedding suit. Their orthopedic support is also top of the line. Standard sizing tops out around 14 and styles are generally priced anywhere from $110 to $200.
Cole Haan: From shoes featuring athletic support usually seen in sneakers to dress shoes with flexible, feet-friendly builds, Cole Haan has long been one of the most trusted sources for comfortable dress shoes on the market. With a product range that spans classic oxfords as well as more fashion-forward selections, the brand offers up to size 13 (standard width only) and pricing ranges from $110 to $300.
