The Winter Reboot

By Sharon Mosley

January 28, 2020 4 min read

Look down at your feet. It's winter, and chances are you're wearing a pair of boots. Whether it's a pair of thigh-highs or wedges, boots are one of the fastest ways to step up the style in your wardrobe this winter. Do some fancy footwork and slip into one or more of these trends right now. You might even find some of them on sale! Time to reboot.

— The thigh-high boot. Yes, it may be going to extremes, but the taller boots have sky-high style. These over-the-knee boots (they're best with a little stretch built in) can be worn over slim pants or skinny jeans, or paired with shorter dresses and skirts. Wear them like tights.

— The lace-up boot. This is not your traditional granny boot. Think a little more equestrian-inspired with a boho folkloric twist. Find lace-ups in all kinds of boots, from funky flats to dramatic thigh-highs.

The extra touch this winter? Lots of fuzzy faux fur trim. How's that for cozy?

— The Chelsea boot, also known as the Beatle boot. Vogue calls this the only boot you'll need this year. A rock 'n' roll favorite, this flat ankle boot may be one of the most comfortable ways to put some cool back into your wardrobe. Go for the pointed toe and a few buckles for even more of a rocker look. Wear them with cropped pants or shorter skirts and bare legs (if you dare) for an updated vibe.

— The biker boot. The punk-inspired boot that rides into winter comes in all shapes and sizes. From chunky-soled work boots with lots of metal hardware to combat styles with lace-ups, these boots have lots of rough-and-tough style that give your outfits attitude. Wear them with miniskirts and dresses, and team them with lace socks for even more punky pop.

— The wedge: another favorite boot this winter. Wedge heels are making big strides into the colder months with platforms reminiscent of the '70s. When you need comfort, this is the boot that you will come to rely on day in and night out. Wear them to give you a little lift with flared pants, long skirts and tailored suits.

— Slithering snakes. Snakeskin may also qualify as the boot of the winter season. Snakeskin, the fashion favorite, shows off in slinky knee-highs or fun ankle booties. Dress up your casual outfits, and give them an edgy vibe. These boots are definitely eye-catching accessories and will up the style factor on any outfit.

— Snow boots. And of course, what would winter be without cold-weather boots? For rain or snow, a pair of waterproof boots is one of the season's necessities, especially if you live in a region that gets a lot of icy precipitation. While function is very important, snow or rain boots can also be fashion forward with decorative linings, fur trim, fun soles and lace-up details. Ditto for hiking boots. When you try them on, always remember to leave room for socks!

Hike down the city streets in style with plaid boots by Jessica Simpson.
Hike down the city streets in style with plaid boots by Jessica Simpson.

To find out more about Sharon Mosley and read features by other Creators Syndicate writers and cartoonists, visit the Creators Syndicate website at

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