It’s tough to find the perfect pair of men’s boots, but once you do it’s even tougher to take them off. We don’t mean literally—boots, despite their rough-and-tumble nature and high-top silhouette, are mercifully easy on your dogs after they break in. We mean stylistically: there might not be a single shoe on the planet that looks just as good with beat-to-hell jeans and your old man’s Barbour jacket as it does with a nubby tweed suit and a slick trench coat. (Our sincere apologies to your derbies, loafers, and sneakers; it had to be said.) The trick, then, is finding the perfect pair of men’s boots for you.
Are you more of razzle-dazzle Chelsea Boot kinda guy or a plainspoken work boot fella? Do you prize functionality above all else, or are you happy to compromise slightly on blizzard-busting prowess when the occasion demands it? And, perhaps most important—are boots really a year-round staple? To help you answer all those impossibly pressing questions, we went deep on every boot style worthy of a spot in your already-crowded front hallway. The latest episode of the GQ Recommends Show is a font of footwear-related information, jam-packed with useful tidbits, practical how-tos, and plenty of styling tips from the experts—namely, us.
For better or for worse (we’d say for better!), there are lots of boots to choose from. So we whittled down the genre into seven key categories you should familiarize yourself with before smashing that buy button—and then rounded up a few excellent options from the biggest names in the biz. Keep scrolling to see how your collection stacks up, and then browse a few of our favorite boots below.
Watch The GQ Recommends Show: 7 Must-Have Boots
1. The Alpine Boot
If the inimitable cool of après-ski style sounds like your cup of hot cocoa, a chunky turtleneck and sturdy cords will only get you so far. But add a pair of rugged, slopes-ready boots to the equation and suddenly you’re an ’80s-era A-lister, slaloming your way to Pinterest glory—or, at the very least, the picturesque lodge at the bottom of the mountain. Danner’s been hand-making its signature stompers in Portland, Oregon for close to a century, and after all these years they still remain the epitome of the form.
2. The Chelsea Boot
Chelsea boots are sleek, smooth, and easy to get into. The pull-on silhouette comes with no laces to trip you up, which gives it a streamlined look perfect for dressier affairs. The Wyatt is an archetypal version of the style, crafted in Italy out of calfskin leather that’s durable but still pliable (crucial for a shoe like this, which you want to look great but also to actually walk in—a lot). Should you find yourself performing in front of thousands at MSG, these are the only boots worth doing it in.
3. The Hiking Boot
Trekking through tough terrain? Making good on a forgotten promise to enjoy the outdoors with your friends? You’ll need an actual pair of hikers to help you survive nature’s playground—boots with great cushioning, heavy-duty water-resistance, plenty of breathability, and, naturally, grippy rubber outsoles. Of course, the raddest options—like Merrell’s “Mother of All Boots”—also take easily to the concrete jungle, where the most grueling demands they’ll be subjected to are that of your own drip.
4. The Dress Boot
Not all boots are designed to help you scale cliffs or slog through the mud. Sometimes, duty calls for a boot that can charm its way through high society and hop from a luncheon during the day to a gala at night. When that time comes, Thom Browne’s brogued pebbled-leather joints will be more than up for the job.
5. The Cowboy Boot
The most surefooted way to get your style point average up is with some rodeo-ready shoes. Cowboy boots come in a grip of silhouettes, often accented by intricate stitching, lofty heels, and sharp toes. We dig Tecovas’ for a few reasons—the impeccable craftsmanship, the authentic yeehaw-ready vibe—but mostly because you’d be hard-pressed to find a better option for the price.
5. The Rain Boot
When the forecast is predicting showers, an umbrella and a raincoat, no matter how good, will only get you so far. (Need we remind you how absolutely grody wet socks feel?) Don’t risk stepping out in sneakers—or boots!—that aren’t built for inclement weather. Get yourself a pair of the Bean’s legendary chain-treaded stompers—introduced in the early 1900s and refined to perfection in the time since—and glide through slippery weather with swag.
7. The Work Boot
Spending long hours on your feet with a bunch of tools strapped to your belt? (Or just want to play up the workwear energy in your daily fits?) A pair of high-quality work boots is what you need. Ideally, you’ll want something with supreme cushioning, comfy and grippy rubber soles (look for that Vibram stamp), and maybe even a steel toe or two. In other words, you’ll want Red Wing’s just-chunky-enough moc-toe boots, a GQ-approved style Ryan Gosling’s been wearing for years—and you will, too.