Long a product of the highest craftsmanship and design, shoes are your connection to the ground and a sign that you care about the small details (or you don’t). If you invest in a quality pair and take good care of them — by cleaning, polishing and storing them on a cedar tree — they’ll last for years, with the occasional repair.
While there are strict guidelines in some circles as to what qualifies as formal footwear, we take a more holistic approach: if they look good and you like wearing them, well, then wear them. But it's best to start your search for your next dress shoe by type — beginning with the pillars and making your way out toward something more statement-making with time. Be practical: Try an Oxford or Brogue off the bat, but set your sights on a loafer or mule next. We've made the work of finding all of these easy, though. Find three options for every type of dress shoe — Oxfords, Brogues, Bluchers, Derbies, Loafers, Mules and Monk Straps — below.
The oxford is characterized by lace eyelets that are attached below the vamp, as opposed to open flaps as with the derby. This leads to a closed seam above the tongue, and a sharp, neat look.
An all-black Oxford that works as well with jeans as it does a black suit.
The Park Avenue Oxford is a classic — and for good reason. Can't you tell?
Tezo's Derby isn't super wild, but it does have a wedge sole, which makes it stand it in a sea of similar dress shoes.
Pebbled leather has a polished appearance but also lots of texture — a two-for-one, in my opinion.
Not your usual derbies, Paraboot does its with a unique toe and a higher, tighter lace construction.
Decorative and elaborate meets sturdy and traditional with the brogue. It’s primarily characterized by its low heel and multi-piece construction, which gives it a layered and detailed look. The perforations may not work to drain water on a stomp across the marsh as they were originally intended, but they will certainly catch the eye.
When I think of Brogues, these by Tricker's come to mind: classic, simple and made from soft (yet sturdy) suede.
This shade of suede will match any suit: brown, blue, patterned tweed, textured cord; your call.
From Blackstock & Weber's FW21 collection, these two-tone Horse Bit Loafers are traditional luxury with contemporary flair.
Sleek and simple, these loafers from upstart brand Vinny's aren't too stiff to seem cool.
Viberg calls this a slipper, but it counts as a loafer in my eyes.
Named after a late-18th-century Prussian field marshal general who commissioned the first boot of this style for his troops, the blucher is fit for war. Or, more appropriately, a business-casual event. Don’t confuse it with the more formal oxford, which has a closed connection between the vamp and laces.
Orangish-brown Longwing Bluchers from Alden, available only at J.Crew.
The Plain Toe Blucher from Grant Stone gives you the look of an Oxford without the bulk.
These Alden Bluchers come unlined, meaning they'll lighter, more flexible and more breathable in warmer settings.
Rich, chocolate brown double monk strap shoes by John Lobb. Say that six times fast.
These squeaky clean dress shoes by Church's will make a statement with a matte suit and pair super well with a tuxedo.
Santoni fuses two types of footwear here: loafers and double monk strap dress shoes. The result is an interesting, incredibly sophisticated hybrid.
Mules are having a moment. The slipper-like style was born from the habit of crushing the heel of your shoe, whether because it made them easier to take on and off or they gave you blisters. But it's been around, and especially so since Gucci launched its fur-lined slipper in 2015. Brands nowadays are adding bigger, more durable soles to their mules, making them something you can wear all day without fear you'll burn through the outsole.
The Ellis pays homage to our collective bad habit. You can wear it with the heel down or up, and I found even after a few up-downs it still held its shape.
These Ferragamo slippers have a significant sole, even though the shoe as a whole is rather understated.
Viberg gives its Dublin Mule as a boot-like tread and a sturdy, all-leather upper.