Chelsea Boots
With no laces to tie you up, 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-ups 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?
Cowboy Boots
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 cowboy boots. Hell, they're more fun if the only lasso you're familiar with is Ted.
Tecovas "Johnny" boot
Desert Boots and Chukka Boots
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.
Crockett & Jones
Chiltern Suede Chukka Boot
Dress Boots
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.
Hiking Boots
If you're hoofing it through woods and traipsing up trails, then an actual pair of hikers tis 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.
Rain 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.
Work Boots
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.
