Named after the swinging central London area where every stylish kid wore them in the early ‘60s, the Chelsea is the dressiest, most elegant boot out there. But don’t go thinking elegant means stuffy; dandies wear ’em, but so does every rebel style god we can think of.
What you need to know: Chelsea boots require slim pants—and that’s it. It’s that simple. The streamlined cut of shoe looks best under a pant leg with a light break (or none at all) and a narrow leg opening like you see here. Those two small-but-crucial details will ensure you look taller, leaner, and ready-to-get-shit-done-er than you would with boots peeking out from under pooling pant legs.
The Office-Ready Combat Boot
Imagine an old Italian cobbler got his hands on some Doc Martens, and you start to get the idea. They’re always black, always shiny, and always ready to make even the most refined suit a little tougher.
What you need to know: There are combat boots, and there are combat boots you can get away with at the office. The above pair is the latter, defined by a less bulbous toe and lug-free sole. Essentially, the right ones have more in common with your dress shoes than actual field-ready boots—they’re just higher and come with a heaping dose of badass-ness. Plus, they have the right proportions (read: not too narrow, not to thin-soled) to handle a cuffed hem.
The Refined Mock-Toe Work Boot
A work boot with an edge—literally. The mock-toe detail—that raised semi-circle at the front of the shoe—is a touch that hasn’t been in style since guys were sporting ancient boots under heavyweight selvedge jeans a decade ago. These are the dressier spin on the workwear staple, ready for a corner office and a commute in shitty weather.
What you need to know:
These boots look like they’ve put in some time on an old-time factory floor, but they’re made with as much care and consideration as any other pair here. Their rugged vibe is the perfect counterbalance to your go-to wavy suit: they’ll ground even the most pumped-up colors and patterns (like, say, a gingham suit).
The High-End Hiking Boot
Just what it sounds like: a hiking boot heavy on the luxury details. The silhouette is pulled straight from old-world mountain trekking shoes, even if all you’re going to do in them is climb the corporate ladder.
What you need to know: Even done up in luxe suede, these boots scream “outdoors.” So when you’re anchoring a suit with them, you want that suit to be the most elegant one you own (i.e. a lightweight wool flannel in dove gray). The contrast of classic tailoring with something so utilitarian—even in its souped-up form—makes these boots eternally wearable—even on the days it’s not a snowy mess outside.