The Best Boots Steamroll the Rest of Your Shoe Rack

If variety is the spice of life, then you can think about your boot collection as a stylish spice drawer. Curate yours into a Michelin-starred pantry of the best boots for men, and you’ve ensured that every fit will be a feast for the eyes. But like any nascent culinary wizard, it’s can be overwhelming to know exactly what spices to stock. Even with all-spice, or everything-but-the-bagel seasoning, there’s no singular universal herb or flavoring. Same goes for boots.

Even the most adaptable boots aren’t enough sometimes. That’s why you should have a few different boots in your rotation to make sure you’re covered. Maybe that means a beefy work boot for the job site, which you can rock before swapping into a dressy pair of Chelseas for a romantic date night on the town. Or maybe you need some slush-proof snow boots to tackle Nor’Easter as well as a pair of cowboy boots for when you go back home to Austin.

Boots come in many flavors and if you’ve got no idea where to begin, consider this your palate expander. We’ve compiled the ultimate grocery list of the best boots for men right here. So scroll forth and boot up.

Whether you’re spending long hours with a bunch of tools strapped to your belt or you’re spending long hours crawling drive bars with the wind at your back, a pair of high-quality work boots makes sense. The beauty of the best work boots is in their supreme cushioning, comfy and grippy rubber soles (look for that Vibram stamp), and better-when-beaten looks. They’re also sneakily under-the-radar after the Great Menswear Boom of the Aughts left everyone needing a breather. If you’re looking for a pair of boots to actually get some work done (as opposed for strictly flexing), keep your eyes peeled for American craftsmanship and goodyear construction for durability, and a built-in shank for arch support.

If you think the dress boot is the softest of the crew, let us explain just how much heavy lifting it can do. A dress boot can take a suit from fine to f***-yeah by adding a little extra edge. A dress boot, some great jeans, and a sport coat is a go-anywhere hack. A minimalist dress boot, some big jeans, and a slouchy button down is a real fit. Not to mention, a dress boot offers worlds within worlds: cap toes or brogueing or texturally satisfying pebbled leather or a beefy rubber sole for giving the middle finger to long walks and hard rains. Black boots will always be dressier than brown boots, but we wouldn’t get too caught up in color theory.

If you’re hoofing it through woods and traipsing up trails, then an actual pair of hikers is warranted. But you don’t need to be romping around Mother Nature’s playground to get the benefits of boots with great cushioning, heavy-duty water-resistance, plenty of breathability, grippy rubber outsoles. Hell, you’ll probably be more grateful for their survival-ready specs the next time you’re strolling a skyscraper canyon and accidentally step into a sinkhole-deep puddle. Each of these pairs is built to by a brand that knows how to go off-road, but can sync up with your city style, too.

With no laces to tie you up, the best Chelsea boots keep things simple and straightforward. They also run a dauntingly wide gamut from dressy to down-n-dirty, with some styles able to be all things to all people. Sleek leather-soled versions still bring frontman cool to a suit and jeans. Beefy lugged-sole versions are happy to roll up their sleeves and get to work, particularly if your work veers more chore coat than sport coat. In between, you’ve got everything from everyday welted-sole Chelseas to some far out fashion explorations. Which is to say: you may need more than one pair of Chelseas.

Combat Boots

Somewhere between work boots and dress boots are combat boots. They’re usually unadorned leather lace-up boots riding on chunky rubber lug soles, and they appeal to everyone—from the heady avant-garde to vintage-loving thrifters to the Dr. Martens devotees. Our favorites veer more punk than tactical. If they look like they came from the Zero Dark Thirty set, you’ve gone too far. Black is classic. But what’s punk about being classic?

This is a mild take at best: Cowboy boots are the most swaggering of all the boots. Seems obvious, right? It’s all that intricate stitching, the high-rise heels, the sharp toes. And listen, you absolutely don’t need to be clicking your heels down to the local honkey tonk to pull off a pair of western kicks. Hell, they’re more fun if the only lasso you’re familiar with is Ted.

If you’re hooked on sneakers, these boots will be your gateway drug to a life beyond EVA midsoles and loud logos. That’s because desert boots and chukka boots offer maximum comfort without compromising on their essential boot-iness. Suede makes things not only softer but less serious than leather. The difference between the two is more of a technicality: a desert boot originally had a more cushioned crepe sole, while a chukka had a dressier leather sole. The silhouettes are essentially identical and no one’s really following those rules anymore, so ignore the nomenclature and just enjoy your new boots.

When weather app has drops showing—or, god no, the lightning bolt—an umbrella and a raincoat isn’t enough. (Need we remind you how absolutely grody wet socks feel?) The best rain boots are built precisely for this situation: rubber-powered, waterproof, grippy and easy to hose down. Get yourself some all-season rain boots or slush-defying insulated winter boots, and glide through nasty weather with swag.

One man’s winter is another man’s spring and while rain boots might get you through a February in Los Angeles just fine, the boots that have earned the “winter” status are prepared for much worse. Winter boots are more than just waterproof boots. They should be adept at blocking sleet and snow, too, so expect taller boots made with plenty of rubber and Gore-tex. They should be able to plow through snow banks and keep their footing through slippery ice patches, so you’ll want boots with some beefy, lugged soles. And lest you want your little piggies to get frost bite, winter boots should come with insulation like sherpa or wool linings, and down-filled uppers.