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How to Wear Boots this Winter

Boots are a ubiquitous part of winter. Whether it’s snow-boots and sweats for shoveling the driveway, knee-high boots worn over skinny jeans for a night out, or duck-boots peeking out from under dress pants as you commute to the office, wearing boots is more often a functional rather than fashionable choice during these colder months. However, it doesn’t have to be. There are a variety of stylish winter boots out there that will keep your socks dry and also keep your style fresh as we slog through the snow, sleet, wind, and rain. Here are a few cold-weather outfit formulas featuring fashionable — while still being practical — footwear to keep you looking your best this winter.

Not all waterproof boots are rubbery pull-on wellies. In fact, many of your favorite shoe silhouettes now come in a winterized version. Sorel’s Joan of Arctic Wedge is a Chelsea style boot in waterproof leather, synthetic lining, comfort footbed, and rubber outsole. You can pair this wedge boot with opaque tights and an A-line skirt, then top it off with a patterned blouse layered under a V-neck or cable-knit sweater. This boot style will also work great with mini to mid-length dresses. Just be sure to keep those legs warm with tights, knee-socks, legwarmers, or a combination of all three to really play with texture and pattern.

Dresses also wear well with cozy lace-up boots, like LL Bean’s Signature Tumbled-Leather Shearling-Lined boot. The broken-in leather will contrast well with a more feminine maxi-dress for a romantic, yet weather-appropriate look, while the shearling will keep your feet, calves, and shins warm and cozy. Pull on an oversized cardigan for even more coziness, perfect for a winter evening out and about. You can also pair this boot type with sweater dresses or a knit shift for a daytime look.

For a casual day, either at work on running errands, try a performance-based boot, like Columbia Sportswear’s Newton Ridge Hiking boot. Built with waterproof suede in a classic mountaineering shoe style, this boot will play into the outdoorsy feel of corduroys and a turtleneck sweater, while keeping your foot supported when trudging over icy terrain. You can also wear a hiking boot with black, cropped jeans, graphic tee, and hoodie for a more rustic take on streetwear.

Of course, not every stylish boot is rustic and clunky. Sam Edelman’s Jaclyn Chelsea Bootie tends more toward the chic end of the style spectrum in both black and dark taupe suede. This waterproof boot with exaggerated tread and easy to slip-on gore insets pairs perfectly with work-wear staples like blazers, cropped chinos, and wool culottes. And depending on the length of your pant hem, this cold-weather footwear can also work with formal business suits just as well as it does with frilly party dresses.

Lastly, there are the go-to duck boots. I really love the Sherpa Lined, Dark Caramel Houndstooth version from Lands’ End. They are quite the leader of the quack in terms of fashionable yet functional footwear this winter with a waterproof rubber shell, Thermolite insulation, and a patterned shaft. These boots bring a bit of quirkiness to your standard sweater and jeans ensemble, as well as when you pair them with a shirtdress and fleece-lined leggings.

Sales are going strong from all of these brands, so now is the time to invest in a quality, stylish boot to see you through the rest of winter.

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