Every guy should have a good pair of dress shoes in his closet. The right pair of dress shoes is a workhorse wardrobe addition, the sort of shoes you can pair with a black-tie look or a more casual pant to spruce it up. Dress shoes are high-quality pieces that you buy to keep in your wardrobe for years. They aren’t like sneakers; you aren’t aiming to collect new silhouettes and colorways once a month. The right pair of dress shoes is the one you buy once and don’t have to think about again until years down the line when you get them resoled (and begin the cycle again).
What the Experts Say
When picking out a pair of dress shoes you could take any number of factors into consideration, be it color, detailing, materials, or sole. “For me,” Libero founder and CEO Adam Appugliesi explains, “It comes down to two things: color and how it looks when I look down while wearing it.” Appugliesi says the color of a dress shoe (and the finish, both of which tend to reflect the quality of the materials) often is the difference between looking, “like a finance bro and looking like you have a million in cash on you.” He’s also big on silhouette, telling SPY,“I don’t want to look like I’m in middle school with a long shoe that sticks out 2 or 3 inches past my toes. I want it tidy and sharp.”
Beckett Simonon Dean Oxfords
For under $250 the folks at Beckett Simonon will get you laced up in as classic a pair of dress shoes as you’re going to find. Their simple, sleek black cap-toe oxfords are going to look as good with a suit as they do with a pair of simple straight-cut jeans.
Morjas ‘The Derby’
Menswear heads may know Morjas best for their stellar line of penny loafers but the brand does much more than that, offering a take on almost every kind of classic dress shoe in the game. Their derbies are especially killer, featuring all the right kinds of eye-catching detailing and the same stellar construction that has made the brand a cult classic.
Swedish shoe makers Myrqvist may be the most slept-on dress shoe designer in the business today. They provide some of the most bang for your buck you’ll find in a pair of dress shoes and many of their silhouettes feature quietly innovative and disruptive design. Take the Vadstena for example. Their take on the classic monkstrap dress shoe, it features a pared-down design that feels just left of center when it comes to the tradition of the shoe.
Crockett & Jones ‘The James’
Yes, as in Bond. James Bond. Crockett & Jones are legends of British clothing and outfitted Daniel Craig during his run as the iconic superspy. This silhouette, named after the character, is featured in a number of Craig’s screen appearances. It also happens to be one of the best dressy dress shoes in the world. It’s sleek, elegant, and made to last a lifetime. Throw these on with a tux and you’ll look and feel like the man himself.
Cole Haan Hawthorne
Cole Haan is the most recognizable name in dress shoes for a reason. For decades now the brand has made quality leather shoes accessible and affordable for the masses. Don’t thumb your nose up at them – they know what’s up. Their Hamilton is a simple, classic brown dress shoe at a super affordable price. If you’re aiming to keep your budget tight these will have you going home (or at least clicking ‘confirm order’) happy.
Yves Saint Laurent Army Derbies
Dress shoes don’t have to be stuffy or boring. They can have just as much rock star swagger as a beat-up pair of Chucks or a badass pair of boots. YSL’s derbies are as great a testament to this as anything, swapping out subtlety for swag. With a chunky sole and a matte finish, these will have you turning heads at a wedding or a on a coffee run.
Blackstock & Weber Ellis Penny Loafer
Laces are overrated. Guys looking to sub out classic dress shoes for a perfect pair of penny loafers just hit pay dirt. Blackstock & Weber has become one of the hottest brands in all of menswear for their modernized take on the American classic. They’re available in a wide array of colors that sell out quickly but if you’re looking to keep it simple and dressy, go with the Ellis in black.
John Elliott Derby Creeper
Don’t let the name scare you off. Creepers are dress shoes (often derbies) with a chunky rubber sole, popular in the punk and alternative scenes. They bring an edge to any outfit and if you’re looking to channel some of that energy the next time you lace up a pair of dress shoes, John Elliott has you covered. The brand’s take on the creeper is a chunky joy, made from stellar materials and making for a silhouette unlike anything you have in your closet right now.
Frequently Asked Questions About Dress Shoes
Can I only wear dress shoes with a suit?
No! Go nuts! Dress shoes can be used to pep up some otherwise ordinary looks. Pair them with jeans and a blazer to keep things elevated. Just don’t use them anywhere you’ll scuff them up too much and they can still be used for your next formal affair.
Are dress shoes different from tuxedo shoes?
Yes. While you can wear black dress shoes with a tuxedo, tuxedo shoes often have a shiny gleam to them. Additionally, while not all dress shoes need to be black, all tuxedo shoes are.