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Choosing the right shoes to wear to a wedding can feel like an afterthought, particularly if you invested a decent amount of time in picking out a suit that fits the occasion. Don’t fall for it. The wrong shoe can negate the hard work you did picking the right outfit, with the added indignity of making your feet hurt.
On the other hand, the right wedding shoe can elevate your outfit, enable your celebrations, and generally be the difference between a great time and an OK time. And while you can spend thousands of dollars on custom-cobbled, bespoke, or otherwise extravagant wedding shoes, it’s also possible to get a great pair of handsome dress shoes for less than a mortgage payment, a value that increases every time you get them resoled over the course of a lifetime.
The right wedding shoe for you might depend on your overall fashion sense, the dress code for a particular set of nuptials, and/or the amount of money you have to spend on new footwear. But no matter what the particulars, the next time you hike up a hill for a scenic sunset wedding, spend hours on the dance floor because the band is that good, or have your picture taken a million times by a particularly comprehensive wedding photographer, you’ll be glad that you put some thought and money into the shoes on your feet.
What the Experts Say
Wedding experts are an inherently aesthetically-minded bunch, but even they said that comfort is paramount when shopping for formal wedding shoes. “A good wedding shoe looks good while feeling good,” Dustin Sitar, the CEO of The Groom Club, puts it plainly.
Wedding planner Carissa Kruse of Carissa Kruse Weddings agrees. “The very first thing that I would recommend to any man planning to attend a wedding is comfort. It’s important that your shoes are comfortable enough for hours of standing and dancing, so I would suggest looking for styles that have cushioned insoles and breathable uppers.”
Ryan Mayiras, a veteran wedding photographer and owner of Candid Studios, adds that he recommends shoes with comfort insoles that prioritize comfort and have a non-slip sole. Style-wise, he says you shouldn’t be afraid of a bit of flair. “We recommend a dress show that has unique patterns. These often will subtly stand out, but they stand out just enough to be noticed. A wedding is not a business meeting, so it is okay to have a design that is extravagant.”
John Smith, a textile Designer at Leather Skin Shop, also has some opinions on style. “Classic oxfords or derbies are always a safe bet. While these styles may be considered more traditional, they can be dressed up with the right accents. aIf you want something more modern, try monk straps or slip-ons.”
BEST OVERALL
Allen Edmonds Carlyle Plain Toe Oxford
A classic Oxford is always a safe bet. That’s even truer with a minimally adorned, low-profile shoe like this one from Ted Baker. Its burnished European calfskin leather—available in black, brown, and tan colorways—surrounds CustomCork insoles that mold to the shape of your foot. The 360-degree Goodyear welt construction ensures durability and allows for future resoling to extend the life of the shoe, which makes its $395 price tag (for a shoe that’s made in Wisconsin) an even better deal.
BEST MONK STRAP
Alden for J. Crew Cordovan Monk-Strap Dress Shoes
When the oldest shoemaker in New England collaborates with menswear mainstay J.Crew, take notice. These handcrafted shoes are made of cordovan leather, a thicker and more expensive variety that’s prized for its non-creasing nature, smooth texture, and natural shine. The modern look of the monk strap is balanced nicely by the meticulous stitching and buckle that have more of a classic feel.
BEST CHELSEA BOOT
Allen Edmonds Liverpool Chelsea Boot
In addition to their stylistic versatility, Sitar says that Chelsea boots are “designed for everyday use, meaning they’ll be comfortable enough for an all-day event like a wedding.” This pair has a full-leather upper with rubber sole that can keep you comfortable from the ceremony through the last song of the evening, with more ankle support than a traditional oxford or derby simply can’t compete with.
BEST LOAFER
G.H. Bass Logan Croco Weejuns Loafer
Weejuns, in addition to being a fun word to say, are a classic pair of loafers. There’s the low profile, apron/moc toe, and laceless opening that define the shoe that, in this iteration, are coupled with a naturally textured leather that connotes a certain kind of patrician charm. For a slightly more casual look at a wedding that’s more about a good time than a strict dress code, it’s hard to imagine a better choice in footwear.
BEST PATENT LEATHER
Todd Snyder Loake Patent Leather Dress Shoe
With a long history in military dress uniforms and black tie attire, patent leather is the right choice—some would say the only choice—for black tie and white tie weddings where a different dress shoe would attract the wrong kind of attention. This pair from Loake Bros. features a cemented leather sole and classic patent leather finish that, while far from the most comfortable shoe on this list, is certainly the dressiest.
BEST INSOLE
Dr. Scholl's Custom Fit Orthotic Inserts
Mayiras swears by these orthotics, which come in nearly 40 varieties matched to specific combinations of arch type, foot length, and pressure points calculated from measurements taken online or in an in-store kiosk. If you’re a groomsman who has to wear an uncomfortable shoe or someone who’s always putting form over function, treat yourself to a pair that, according to the experts, can make the difference between a good wedding and a great wedding.
Frequently Asked Questions About Men’s Dress Shoes
What are the most versatile men’s dress shoes?
When you think of a men’s dress shoe, you probably think of an Oxford. Its ubiquity makes it blend in more than more outré choices, which also means it’s easier to wear with a variety of different looks.
What kind of details can make my dress shoes stand out?
You can go all the way and get dress shoes in non-traditional colors, but opting for a pair with some intricate detail work, laces that offer a pop of color, or a particularly striking silhouette can give you a nice balance between fitting in and standing out. As Kruse puts it, “Opt for a shoe with subtle detailing, such as laces or stitching with color. The details should coordinate with the overall look, but give you a unique touch that will make you stand out in a crowd.”
Why can’t I just wear sneakers? Or those dress shoes with the soles of sneakers
You should always err on the side of dressing up for a wedding, and it’s hard to see how wearing the same shoes as a retired football player squawking on one of those miniature fake fields they build in TV studios qualifies.