And in the event that you’d like to trek into the territory of finishing your buttoned-up look with some ruggedness from the ankles down, we’ve rounded up the 12 best hiking boots for the job. (Do the math.)
Take a close look at this snap just in from the Listen Up Philip premiere at Sundance.
You’ll notice that Jason Schwartzman is wearing hiking boots with his otherwise normal-looking suit and tie instead of a pair of hard bottoms. It’s an advanced move that we’ve seen pop up a few times over the years—and like most sartorial affectations, it looks better on the Internet. But we do see a few rare situations in which a stylish gentleman might find it appropriate to wear his hiking boots with a suit. And yes, premiering at Sundance is one of them.
Consider the monk strap. Holy. Strappy. Fits nicely on your feet.
They’re the jack-of-all-trades of footwear: a dressed-up high shine for your company’s holiday party, a casual snuff suede for a Sunday stroll in the park, maybe a middle-of-the-road cap toe for the boardroom.
With so many options/so many occasions, navigating these waters can be tricky—so we went ahead and compiled the essential guide to monk-strapage.
There are few things more autumnally satisfying than the sound of the first brittle fallen leaf crunching underfoot.
Especially when that foot is handsomely leather-clad...
Chances are, you’ve already got a go-to pair of respectably worn-in boots ready for just the occasion. But in case you’re in the market for an update, we’ve taken a moment to round up the best heavy-trodders new for this fall—from the trail-worthy to those suited for more urbane purposes—ensuring that, no matter where you are when the time comes, you’ll be handsomely prepared for some freshly raked destruction.
But if you’re in the market for some handsome shell cordovan leather wingtip cowboy boots, look no further than these Wingtip Ropers from Yuketen that have recently arrived at Context Clothing. Here’s what else you should know about them:
The Story: Yuki Matsuda has been heading up the Japanese-led Americana revival for nearly three decades, while making some incredible American-made shoes along the way. But for these boots, he’s leaned on the ranchero expertise of Mexico—where they’ve been meticulously crafted from Horween shell cordovan #8 in a limited run.
Who to Channel: Whatever a dandified British-Texan oil baron rancher might look like—perhaps a mashup of Prince Charles and George W. Bush.
Or Spend Your $1,114 On: 12.9 barrels of crude oil, an old pickup truck or a shell cordovan leather wallet to hold your remaining $1,000 in.
And here’s a good curious addition: the 4553 Tartan Panel Boot. It’s a collaboration between Red Wing Heritage and Brooks Brothers that replaces some leather with a plaid oilcloth panel—so you shouldn’t be sacrificing any waterproofing—and will land you somewhere on the boot spectrum between Americana and trad. (Perfect for the sort of boot wearer who leaves very long and personal comments on A Continuous Lean as well as Ivy Style.) It’s a limited-edition style only available in Brooks Brothers shops, so keep an eye out on your next stop in for some pinpoint button-down oxfords.
And here’s a late-breaking addition: these boxer boots from Tod’s capsule collection No_Code (inspired by legendary editor Jefferson Hack). They’ve taken the classic shape of boxing boots but cut them in the same buttery-soft leather their driving shoes have become famous for—resulting in the most comfortable-looking boots we’ve seen this side of a sneaker hybrid. Plus the zipper down the back means you won’t even have to spend time lacing them—or fiddling with a shoehorn.