Nothing wrecks the vibe of a good outfit more effectively than a bad pair of shoes. This is empirically verifiable. You just need to look at a politician wearing a perfectly nice suit with horrible hybrid shoes—you know the ones; sneaker soles but dressy up top—to see the phenomenon for yourself.
Get the right shoes, of course. You can’t screw up a carefully considered suit with a terrible pair of kicks if you’ve jettisoned all the flawed footwear from your rotation and replaced it with a lineup of lace-ups and slip-ons that always look great. Which is exactly why we’ve pulled together this list of the five shoe styles every guy should know and, ideally, own.
You might balk at the declaration that you need five different shoes just to lay the right foundation for your wardrobe, and that’s a reasonable reaction. As you read through the below, you’ll see that we’ve provided some broader context and a few tips for those who can’t—or won’t—get everything at once. The idea here is to give you the necessary guidance for building, over whatever timeline works for you, a collection that can handle pretty much everything life could throw your way, style-wise. (So we’re not including exercise gear, which should be considered from a “function-first” perspective.) Whether you’re busting out the tux for a black-tie gala, trying to impress the in-laws over dinner, or simply popping out for a cup of coffee, these are the five shoe styles that’ll serve you well—and, if you take care of them, for many years to come.
A couple of years ago, in the fall/winter 2024 edition of the Big Black Book, we posited that derbies are the most versatile shoes you can own right now. Rooted in classic menswear but designed for casual use, they’ll pair perfectly with everything from a tweed or corduroy suit to beat-up jeans and a white tee. We know guys love their sneakers, but if you could have just one shoe, we’d heartily recommend the derby.
The problem is, a lot of brands out there call their shoes by all the wrong kinds of names. So we need to get a little bit technical for a moment. You can identify a derby by its “open” lacing system, in which the facings (the parts that have the eyelets) are sewn on top of the vamp (the front part of the shoe).
That’s what differentiates it from its more formal cousin, the oxford, which has a “closed” lacing system in which the facings are sewn into the vamp, creating a dressier and more streamlined look. You can find all sorts of derbies out there—with broguing, with split or moccasin-style toes, with wing tips or cap toes. But our favorite, when it comes to sheer adaptability, is a simple, rounded, plain toe.
Extract — continue reading at the source.
