Suits get all the attention in men’s formalwear but it’s really the shoes where one can push boundaries or adhere to strict fashion praxis. I tend to lean towards the basic suits – navy, dark blue, grey, charcoal, light black, faded black, and black – while I let my footwear shoe off a bit more personality.
With the warmer days ahead and your betrothed friends playing catch-up on weddings since Covid, I’ve put together a list of 15 dress shoes for any event. Whether you’re looking for something that’s one-off for a special event or a shoe you can integrate into your daily business-casual wardrobe, we’ve got you covered.
What Counts As Dress Shoes These Days?
But first, we need to answer the existential question of “What, exactly, makes a dress shoe?” Well, that’s about as easy to answer as “How long is a piece of string?” Typically speaking, a dress shoe is anything that accompanies or complements formal attire. Now, this may seem like an obvious answer, but so often people get it wrong. One needs to look at the entire ensemble of an outfit to gauge a) the formality and b) the aesthetic and c) the comfort for the evening. For, say, a summer wedding you’ll want to go for airy fabrics and shoes that are a bit less formal and more functional. For a black tie affair, you’d be better off erring on the side of luxury and keeping it simple so the focus is on the ambience of the evening (it’s quite gauche to be too showy at a formal event). And for those types of occasions where a chino will do – well, you’re in luck. You’re able to get away with just about any oxford, boot, or brogue that cross your path. Keeping it simple is key. Everything else tends to fall into place from there.
Best Dress Shoes for Men
Amberjack – The Original
What first intrigued me about Amberjack is their simple (and effective) branding. It’s clean, fun, and young. Just like The Original, which is one of the top picks for dress shoes this season. The tech behind these shoes is almost that of an athletic shoe, including arch support, outsoles, and durable materials for long-term use. If that’s not enough, they’re available in leather and suede options with eight colors to choose from.
Thursday Boots – Scout
Thursday Boot Co’s Scout shoes are toeing the line between Brooklyn and Buckingham, giving us a bit of American ruggedness mixed with a refined posh sensibility. I love the clean lines of this tucked into a nice pair of dark jeans as much as I would in a linen suit for contrast. What’s especially nice is the clean paneling that’s not bogged down by weighty laces. When real estate is this small, every detail counts.
Sabah – Beirut Black
Sabahs remain a mainstay on my list of shoes for 2022. Here, I’m giving you a black option; but really, I’d recommend any of their colorful varieties. These shoes *need* to hit cult status ASAP. They’re the sort of shoe that is so versatile, so easily integrated into one’s wardrobe, you’ll end up buying pairs for any occasion – and, say, a beach wedding is the perfect excuse, in my opinion.
Stubbs & Wootton Venetian Slippers
Stubbs & Wootton has always been my go-to for shoes when I really want to add a flair to my wardrobe. For my 26th birthday celebrations, I bought a pair of loafers with roosters embroidered on them. And last Christmas, I bought a pair of velvet ones as a Christmas present to myself. Now, these Venetian slippers? They’re heaven. Muted but not boring, these dress shoes are a perfect accompaniment for your next black-tie affair.
Steve Madden Nunan Plain Toe Oxford
Steve Madden should get some kind of award for being the go-to shoe for high schoolers going to prom, econ majors at their first big interview, and middle American grooms alike. These shoes transcend generational differences and are usually found at any department store you may find yourself in. I’m partial to the Nunan oxford for its simplicity and price point. You really can’t go wrong with this dress shoe that’s a favorite for, well, anyone, really.
Gucci Jordaan Loafer
Some may consider this the crème de la crème of the dress shoe game and, really, I wouldn’t want to disagree. The Jordaan loafer is a classic whose silhouette was as great in the 1970’s as it is today. Coming in a variety of tones and leathers, this shoe is a versatile staple that will dress up any outfit while maintaining a bit of Italian cool that’s sorely lacking in American dress shoes.
Ralph Lauren Asher Monk Strap
Monk straps are not an easy shoe to pull off, let alone to style appropriately. They’re a bit too Steampunk for some, a bit too hieratic for others. But I tend to find that the less attention one brings to the shoe the better off it is to stand on its own merit. Ralph Lauren does the classics right and so I trust that the Asher Monk Strap is one that can very easily be purchased for a more casual affair – think dark jeans and a nice light sweater.
Crockett & Jones Barrington 2 – Tan Antique Calf
I’d be remiss to not include a Crockett & Jones dress shoe on the list. With its attention to design, the Barrington 2 is the oxford I’d want to wear all through summer and into winter. A rich leather that’s bark-tanned, one can appreciate the craftsmanship that’s been synonymous with the brand since 1878 and the reason they hold a Royal Warrant or two.
Belstaff Longton Leather Chelsea Boots
Another British heritage brand that I’m quite smitten with is Belstaff. While known for their jackets more than their dress shoes, one shouldn’t discount their line of Chelsea boots. The Chelsea boot had its moment during the heyday of Hedi Slimane, but I’d argue that it can work seamlessly from casual to dressy with just a change of a pant. I quite like Belstaff’s for updating a ubiquitous silhouette to be more in line with its other luxury offerings.
Cole Haan Modern Classics Wingtip Oxford
Cole Haan is another one of those ubiquitous brands that makes the rounds for middle-management and literary types alike. A pared-down Oxford, they’re as much about formality as utility, giving nothing more than what the classic design asks for. I think there’s something comforting in that. Plus, the leather has a subtle grain in a honeyed tan that’s perfect for just about any occasion.
Beckett Simonon Yates Oxford
Made from Italian leather with some extra holes thrown in for good measure, these Oxfords are a dreamy blend of formal and fun. I quite like that Beckett Simonon isn’t taking itself too seriously with this shoe, giving us the run-down on how they’ve updated the style for the modern customer while still maintaining a brand identity in formalizing the classics. And, bonus, they’re on sale right now.
Sperry Original Boat Shoe
Add a little prep to your step and get a new pair of Sperry’s for your next dress shoe. It’s a bit cheeky and altogether Ivy, but it’s that self-awareness that makes one able to pull it off. Go all out Vampire Weekend on this one: checkered oxford, Ray-Bans. Hell, throw in a tousled hairstyle and a five o’clock shadow and you could be fronting Coachella in no time.
Brunello Cucinelli Wingtip Brogues
By far the most expensive on this list, I wanted to include a grail item for those looking to really up their shoe game. It’s no surprise that Brunello Cucinelli would take the same design philosophy to his shoes as he does his apparel collections. Known for his timeless staples and cashmere, these white suede brogues are a subtle way to say, “I relate most to Kendall Roy” at your next dinner party.
Mr Porter Mr P. Lucien Suede Derby Shoes
I think Mr Porter’s derbies are just asking to be worn. The suede shell is treated in a waterproof finish, making it one that’s good for stomping down the aisle or in mud puddles this Spring. The interior is made of a soft leather, making these a shoe that only gets better and softens with age.
Doc Martens 1461 Smooth Leather Oxford Shoes
Perhaps the most unconventional on the list, the Doc Marten oxfords are actually one of my favorites. I think they add just the right mix of laissez-faire to the dress code while a sort of punk, “Fuck you” thrown in. Now, me being me, I’m quite the meek rule follower, so I’ll have to live vicariously through you if you buy these, dear Reader.
