What To Wear With Your New Winter Boots

If there's a buy out there that needs to count, it's your winter boot. No matter if your walk to work is uphill both ways in 6-foot snowdrifts or a short-but-brutal clip from your car to the heated indoors, if you have to do it in a shoddy pair of boots, you might as well be barefoot. Not only do these babies have to be sturdy, they also have to match with your clothes. Unlike pretty sandals and fun sneakers that allow for skimping on construction, winter boots are made and (literally) broken on their stitching. So, if you're going to spend your money on anything this season, make it a boot made for slogging — not just walking.
But, unless Santa is your neighbor, you probably don't need thigh-high mukluks to get you through. We've got five boots you might want to add to your lineup — for the fall-to-winter days when you still want to look on — and how to work your wardrobe so they really kick.
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The Raining Hard Boot
Unless ladybugs and purple polka dots are really, truly your jam, it might be time to upgrade to a multi-purpose waterproof boot. The thick treads will prove handy, and the heel is solid enough to keep you upright as long as there's no ice around. Plus, you won't have to surreptitiously change out of this pair under your desk.
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Take advantage of this shoe's height by pairing it with a pencil skirt that hits just under the knee. A structured sweatshirt still looks polished (but is way comfier than a blazer). Keep your hands free to carry an umbrella with a crossbody bag, and just watch as a wet, gross day starts feeling a whole lot sunnier.
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The Wintry Mix Boot
In a patent leather, these boots will get you through those spitting, misty, "wintry mix" days. A slimmer-fit shaft will help keep your feet dry, but make sure the shiny exterior is actually waterproof, or you could be sacrificing some nice leather to the elements. You want to show these ankle-grazers off, so think cropped and loose on your lower half.
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Wide, billowy pants are a massive trend this fall, but save those for bone-dry days. Instead, a jogger-style trouser made of thick menswear fabrics like herringbone and tweed give off the fashion-nerd vibe in a more practical-for-real-life way. Balance the look with a feminine shirt and a structured (but soft!) jacket.
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The All-Weather Ankle Bootie
On days when the forecast is wet and chilly, opt for this easy — and waterproof — leather bootie for practical-meets-polished trekking. Slick and icy streets are no match for the rubber lug outsole, which provides great traction to keep you on your feet. The best part? No one will ever mistake it for a rain boot (your secret's safe with us). Advertisement
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While this footwear can work with most ensembles, we like it with a comfy boyfriend jean, a saturated sweater, and a patterned coat. Add a fun beanie and a bright clutch for a quirky mix of daytime and after-hours style staples. Advertisement
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The Cold, But Clear Boot
It's too cold for even tights (though you'll probably wear them under your pants). You need a boot that can accommodate thick socks without creating a bulky silhouette. A chunky heeled boot gives your legs some lift, and a lace-up version gives you the wiggle room to change the thickness of your socks without worrying about losing circulation in your toes.
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Boyfriend jeans work perfectly with boots like this (protect that inch-or-so ankle gap with a pair of thick socks). This sweater-and-oxford combo maintains a long line, while the shorter vest adds a hint more coverage.
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The Party Time, Excellent Boot
Anything open-toed or open-heeled is a no-no in winter, so look for a full-coverage boot with a slimmer heel that's meant for the dance floor.
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Wear it with a long-sleeved dress, tights (obviously), a wide belt, and blingy accessories that give your boot a Marie Antoinette spin.
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The I'm Freezing Boot
A knee-length boot is your answer to really cold days (when paired with insulated socks, that is). A proper waterproof seal is super important to preserve the supple pebbled leather. And, when it comes to styling them beyond that tired leggings-and-tunic combo, you've got options for days.
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You could wear your high pair with skinny jeans, but we love the idea of a just-to-the knee shift dress. Recall '70s vibes with a faux fur leopard car coat and don't forget the tights.