The Best Winter Boots to Wear with Everything in Your Closet

For those days when you need all-weather kicks that still look dress-shoe-good, GQ's Best Stuff has you covered.
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Some winter days, when you’re fighting through slush and sleet and old snowmelt, you need tough-as-nails, extra-waterproof, take-a-beating winter boots. We’ve covered those. But there's another pair of boots you need for the rest of winter, too: for unseasonably-warm-but-still-dodging-some-snow-melt days, for days with just a hint of early-morning freezing rain, and for days when, despite the cold, you’ve got to step out for a lunch with Dave from accounting (who always insists on walking). And for those days, you need boots that will hold up to the elements and look dress-shoe-good with a suit.

Our four favorite pairs, gathered below, are tough enough to wear in just about any weather and they all pack a rubber sole that’ll make that schlep to your car, to the office, and to that lunch with Dave a bit more comfortable. And they fit neatly into classic boot categories—Chelsea, hiker, military, and brogue—meaning you could conceivably grab all four and wear them with everything you already own. The weather might suck. Your boots don’t have to.


Joe Strummer Would Approve
Dr. Martens “Vegan 2976” Chelsea Boots

When you think about Docs, you probably think about the classics: the big, black lace-ups that have graced the feet of punks for decades. But Dr. Martens have a dressier side—in this case twice over, thanks to the Chelsea boot silhouette and old-world oxblood color. You still get the signature nonslip AirWair sole, which you can lord over your colleagues wearing stiff, uncomfortable, extra-pricey leather soles. And best of all: no laces. Winter boots have never been so simple.


Winston Churchill Would Approve
Church’s “McFarlane 2” pebble grain wingtip boots

The folks behind one of our favorite wingtips of all time have done us the favor of applying their brogue expertise to boots. Perfectly nubbly pebble-grain leather is a little less dressy than you average calfskin, but in this case, that’s the point: it’s ultra-hardy and goes with everything, meaning you can wear these Monday through casual Friday, and again on the weekend. Take care of 'em right and your son might even wear them to his first job.


Jean-Paul Belmondo Would Approve
AMI lace-up cap-toe boot

Whether you’re preparing a campaign for the corner office or just launching an offensive against a pastrami sandwich, you’re going to want a pair of military-inspired, tough-as-nails, blacker-than-night boots. These mean business, but the high-shine leather adds a level of polish (pun absolutely intended) to your suits—and even a tux, should you be so inclined. Which you should be: rubber soles that don’t look like rubber soles mean you get away with wearing these under your dressiest gear—yes, even that tux.


Tom Ford Definitely Approves
Tom Ford “Cromwell” hiking boots

Tom Ford is good at plenty of things: not buttoning that many buttons on a white dress shirt, making movies, and having an extravagant bathing routine, to name a few. But what he’s best at is taking the basic closet staples we know and love and cranking the luxury knob up to 11. As you’d expect, these are extremely Tom Ford hiking boots—which is to say, the fanciest, extra-est, most supreme possible iteration of hiking boots, complete with fine, hand-burnished calf leather and brushed brass hardware. Your slushy commute cowers in fear.