Any well-dressed dude or dame will tell you that a great outfit is always built from the ground up. This fall, it’s all about exploring more under-the-radar shoe styles and mixing formal and casual pieces to create your own signature look. If you are one of those guys who only think of grown-up shoes in the context of church, the office or a court case, don’t fret. This fall’s crop of dapper shoe styles is anything but stuffy.

Pro tip: Shopping for the right shoes is all about triangulating the type of weather you will wear them in, the formality of the place you are wearing them to, and of course, your own taste. The best part? All of the shoes included here can easily be styled up or down to fit your needs. And when in doubt, here’s a good rule to remember: The slimmer the shoe, the more formal they will read.


TAKE A HIKE
Forget those wack granola-style hiking boots of your youth. A modern hiking boot needs to be rakish enough to be paired with a cashmere sweater and a thin chain, but also tough enough to make you the best-dressed dude in a blizzard. Our rec? Go with a brand that specializes in these rugged beasts, like Diemme, which has been making them by hand in Veneto, Italy since 1992. As a bonus, you can swap out those bright contrasting laces a few times a year, which will keep your boots looking and feeling as fresh as the day you unboxed them.


BET ON BLUE
Nothing says rock star more than a pair of blue suede shoes. And while these handsome joints from Doc Martens might seem a little flashier than what you are used to sporting, they are actually super-wearable. Pair them with chinos and a white Oxford button collar shirt for an edgy-prep look; or go straight Cobain by rocking them out with a light flannel. Also, we don’t need to tell you this, but these bad boys are just begging to be paired with some bold print socks.


BROGUE UP
Brogues are technically a “country” shoe so think of them the same way you would a fetching tweed jacket—informal but still very elevated. Black brogues are cool because they look as just smart with a grey suit as they do an oversized hoodie. Invest in the best because a great pair, freshly polished, can do triple duty for weddings, meetings and weekends. For our money, there’s no better brogue maker than British footwear master Trickers. Just remember, UK sizes can run a bit big, so be sure to check that you can exchange them if need be.


LOAF AROUND
Tasselled loafers are inherently swaggy because they can make you look both relaxed and refined at the same time. For maximum effect, we recommend finding a pair in deep cherry or oxblood. Not only will your wine-colored dogs pop nicely against jeans and chinos, they will look even more dope once you rough them up and earn your patina. The secret to really breaking them in? Wear them often and style them the same way you would a white sneaker. You will be surprised at how easy they are to work into your rotation.


JODHPUR-FECT
You probably already know that Chelsea boots have been a thing for a few seasons now. And while Chelseas will always be cool, their hipper cousin the Jodhpur is even better, thanks to its slim and elegant silhouette and that nifty strap that goes around the back of the boot. The best part? They look great with pretty much anything: a red flannel, a tweed jacket, a slim-cut blue suit. We like them in suede, but you could also get these in black leather for maximum badass impact.