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. It ain’t great.
So, what’s a guy to do? 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. Let’s get into it.
Derbies
Derbies: wear ‘em anywhere, anytime.
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. This still holds true. 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.
You can get derbies from just about every brand that does proper shoes, which means that the list of labels we’re about to recommend here applies to the rest of the footwear styles we talk about in this article, with the exception of sneakers. (We’ll toss in other notable names where applicable.) Meermin, Beckett Simonon, and Thursday Boot Co. offer solid value near the lower end of the price spectrum, and they all specialize in shoes as opposed to a full “lifestyle” offering, which is a good sign when you’re buying footwear. If we’re talking mall brands, J. Crew is a good spot to look, as is Dr. Martens if you want something less expensive with a little more attitude. Moving up, you’ve got players like Grant Stone, Morjas, Grenson’s G2 line, Vinny’s, and Allen Edmonds (skip the hybrid BS and go for the classics). Stepping over from there you find yourself in the classic English shoemaker space, which covers everything from Cheaney, Loake, and Crockett & Jones to Edward Green, George Cleverley, Tricker’s, Grenson’s G1 line, and John Lobb. If you prefer something Spanish, you can't go wrong with Carmina. French? Paraboot. And for the Americans? Let us never forget good old Alden. We could keep going, but for the sake of all our sanity, let’s consider that incomplete list a solid starting point.
Oxfords
Because of their “closed” lacing system, oxfords are considered more formal than derbies.
You’re going to need a formal shoe at some point, because you’re going to need to wear a business suit—something in dark, slightly sheeny worsted wool, as opposed to a casual suit in cotton or tweed—at some point. The right shoe for a dressier suit is the oxford. As we said before, that’s thanks to the closed lacing system, which makes the silhouette sleeker and sharper. Start with black, because it goes well with navy, gray, and (duh) black. Keep it polished, and remember to use shoe trees after each wear to absorb excess moisture and retain the shape of the shoe. Some folks like a plain toe for an oxford. Some like a little broguing. Some like a wing tip and a lot of broguing. If you ask us, you can’t do better than a cap-toe, sans the perforation.
Wear your oxfords to your next big business meeting or fancy date night if things are going great. Wear them to a funeral or to court if things are going ... not so great. This might offend purists who believe a tux can be worn only with a patent-leather pump, but we think that with a spit polish, you can even wear your oxfords with a tux. Just don’t tell the trads.
Loafers
You can never go wrong with tassels.
Think of loafers as a chilled-out take on the derby. Because they’re slip-ons, they’re just a touch more casual. That means they work very nicely with chinos—crisp or worn in, but we prefer the latter—and oxford-cloth button-downs. Or try yours with fatigue trousers and a chore jacket. And come summer, they’re the best hard-bottom shoe on this list to wear with shorts. But because they have long been a staple of preppy American style, they can—however incongruous some may find this—work very well with a navy suit, preferably from a Waspy institution like J. Press or Brooks Brothers.
As for what type of loafer? Well, the default is a penny loafer. We like the kind with a “beef-roll” detail on each side of the strap. (You can see it on the pair from J. Crew below.) But you can also opt for a more minimalist flat-strap penny loafer. There are also kiltie loafers, tassel loafers, venetian loafers with a totally unadorned vamp, and, of course, the famous horsebit loafer. It’s all a matter of preference, and, really, you can’t go wrong.
Casual Boots
For those days that require something a little more rugged.
Maybe it’s rainy. Maybe you’re walking through the woods. Maybe you revealed that you can’t change a flat tire in front of your partner and you want to look a little more rugged the next time you get dressed. There are many reasons to pull on a pair of boots, and there is no version of life in which at least one of them doesn’t present itself to you in the nearish future.
The question, then, is which pair of boots you need. The answer: not something dressy. Not yet, at least. You’ve already got shoes for any occasion that requires formality. So the boots should be casual. You could opt for bulkier Chelseas from Blundstone, which wear nicely with jeans, feel great underfoot, and have the added benefit of decent weather resistance even though they aren’t billed as rain boots. You could get something like Thursday Boot Co.’s Captain lace-up, which draws from old service boots and looks about as classic as can be. (If you’re looking to invest, Wolverine’s 1000 Mile boot is a nice upgrade. And if you’re looking to splurge, Viberg also does a service boot that is just *chef’s kiss*.) Or you could go the workwear route with something from Red Wing Heritage or Nicks Boots. As with loafers, there’s not necessarily an incorrect choice in the general sense—it’s all about picking what feels right for you.
Simple Sneakers
When in doubt, it’s hard to go wrong with a classic German Army Trainer.
Please, sneakerheads, remember: We’re talking about a pared-down, only-the-necessities list here. If you’re in the culture, a true collector, feel free to hunt down as many limited-edition kicks as you please and let your freak flag fly when it comes to colorways. For the rest of us, a simple pair of sneakers in an easygoing white will do the trick 99.99 percent of the time. Converse makes a great pair. So do Vans, Sperry, Common Projects, Koio, Nike, Adidas, Reebok, New Balance, and just about any other brand you could name. Wear them on a long walk with a friend. Wear them to the park on a sunny day. Wear them for your early-morning coffee runs. Wear them to the office, if your office is cool with it (and most of them are these days).
You don’t need us to tell you what to wear them with. White sneakers go with everything. Well ... almost everything. Unless you want to look as if you’re trapped in 2014—or a European CEO who can’t let go of his youth—don’t wear them with a suit. There may come a day when that look feels fresh again. That day has not yet arrived.
Bonus! (AKA, Some Other Fun Shoes)
Slipper-like slip-ons? Yes, please.
You don’t have to stop at five if you don’t want to. Though the styles above will serve you well in pretty much all aspects of your life, there are plenty of other shoe styles that—while not technically essential—will be welcome additions to your footwear rotation. Some of these styles are more timely, like the ultra-low-profile sneakers that are still showing up on the feet of downtown cool guys who must have very strong arches. Others are perennial, like the much-beloved (if a little weird) Wallabee from our friends across the pond at British brand Clarks. And then there are things like roper boots, engineer boots, and cowboy boots. Clogs and slipper-like slip-ons. Even Mary Janes! Take your pick, man. Just make sure you’ve got enough room to store them all.
