We probably don’t have to tell you that when the fairer sex sizes you up, one of the first things they check out is footwear. And this time of year, as the temps drop and the leaves turn, one of your best bets in this department is boots. Warm, stylish, durable and versatile, a great boot can really take you places. So here are five pairs we love. Chances are, she will too.

Moral Code Bolton ($228): Remember what we said about boots being versatile? Moral Code’s chukka is a shining example. Not only is it light and flexible enough to keep you comfortable on your feet all day, but it pairs well with just about everything. The distinguished pebbling of the leather is an eye-catching bonus feature.

Nisolo Andres All Weather Boot ($288): When adventure calls, Nisolo’s Andres boot is more than ready to step up. The leather is water resistant, the Vibram sole is equipped with heavy-duty lugs to tackle all types of terrain and the gusseted tongue helps you stand up to the elements with dry and cozy toes. And even if you’re taking it easy, the styling makes a winning impression from office to street to happy hour.

To Boot New York Concord ($450): All Adam Derrick’s To Boot crew does is make incredible footwear. OK, they make belts and shoelaces, too, but as the name suggests, the focus is on brilliant boots, and the Concord is no exception. Every detail—from the burnished brown leather to the inside zipper for easy on/off to the grippy rubber sole—is oriented toward optimal form and function. Try ’em and see.

Harley-Davidson Sinclair ($400): Two brands known for craftsmanship and style are Harley and Wolverine. So it’s no surprise bringing them together in the form of this Garage Collection edition of Wolverine’s famed Evans 1000 Mile Boot works so damn well. With a full-grain leather upper, Goodyear welt construction and a Vibram rubber outsole, these kicks will serve you well whether you’re born to be wild or bored to be filing TPS reports. Though we sincerely hope it’s the former.

Thursday Boots Duke ($199): Don’t let the name fool you; these Chelsea boots are ready to rock any day of the week. The Chrome leather upper looks sharp with everything from jeans to a suit, while the full glove leather lining and cork & Poron footbeds ensure all-day comfort. Last but not least, the flexible elastic goring makes them easy to slip on and, once they’ve sufficiently wowed the object of your affection… off.


Lead photo: iStock/Getty Images Plus/Artem Tryhub