The Best Boots of the Season and How to Wear Them

There are few sounds more satisfying than that of a boot crunching down on freshly fallen leaves in late November. To be clear, summer is definitely my preferred time of year in terms of weather—but winter footwear! WINTER FOOTWEAR. It can’t be beat. Ankle boots with a side zipper in a blue suede. Chelsea boots that you slip on—bonus if they have tabs. Glossy knee-high boots worn with a pair of cashmere joggers tucked into them. Edgy moto boots with metal details. Are you salivating? Overwhelmed? A little of both? I’m here to help. Scroll down for a guide to boot shopping this season, broken down by the most important category. (I also threw in some styling tips because I’m an overachiever.)

Combat Boots for Your Walks on the Wild Side

Combat boots can always be counted on to provide durability without shirking on their aesthetic duties. Their utilitarian design means that you can not only walk in them for miles but still maintain your sense of cool  (and joie de vivre) while you do it.

Styling tip: Truly anything (think of them as the boot equivalent of your favorite sneakers), however my favorite way to wear them is with tights and a dress–specifically a full-skirted, super feminine one–for the highest level of contrast.  

Chelsea Boots for When You’re in a Rush

They’re the Shiv Roy vibe in a boot–polished but easy to wear at the same time (thanks to their slip-on design).

Styling tip: I love wearing Chelsea boots with a suit because they’re a great cold-weather alternative to loafers. They also look nice with cropped trousers, so you can just see the top of the boot.

Tall Boots to Keep Your Kneecaps Company

They are the No. 1 boot of fall 2019—and they’ll keep your shins warmer than a chipmunk in a sauna.

Styling tip: Tucked-in joggers (bonus if you add a matching cardigan). Or a dress with a hem that covers the top of the boot. OR, if you’re feeling footloose and fancy free, long shorts because sometimes summer needs to share its spoils with the rest of the seasons.

Platform Boots for Stomping Around Town

They make you want to dance! Such is the power of a platform that is both comfortable and height-boosting at the same time.

Styling tip: Wear with tight pants (perhaps these, which have some sheen) and a blazer or fun jacket or really extra jeans and a lace cami (wear with a warm jacket and gloves while you’re outside).

Pointy Boots for a Quick Polish

You’ve been invited to a nice dinner and you 1.) don’t want to wear heels 2.) do want to look put together 3.) do need to offset the fact that you haven’t been on top of washing your hair this week.

Styling tip: Go for semi-formal pants like these warm, wide-leg, checked wool ones so the boot just peaks out underneath, with a fun shirt. You could also wear a stretch twill slim trouser tucked in or out. Try an embellished v-neck or cardigan sweater on top.

Cozy Boots for Cozy Toes

These are the bear hug of the boot world. They make your feet feel like they’re still in bed even when you’re outside.

Styling tip: Cultivate an après-ski look with these leggings and a sweater like this one with side slits. Alternatively, dress this clog-style version up with a turtleneck-under-dress vibe.

Weather-Resistant Boots for Potential Vortexes

They can take a little water and a little salt without issuing any major complaints.

Styling tip: Pair with a sharp trouser (I suggest a slim onethese have a matching blazer–so the hems don’t get wet). Plus a mug of hot chocolate for morale.

Western Boots for Horse Girls (or, You Know, Whomever!)

They offer a compelling plot twist to the classic tall boot narrative.

Styling tip: Giddy up right into a pair of stirrup trousers or leggings! Oh, and this.

Are you loyal to any particular boot silhouette, or do you love all your children equally? Drop some links in the comment section either way.

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