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Cowboy Boots for Winter

Boots are ubiquitous for winter, and while quality snow boots are worth the investment for the harshest weather, a person can’t live on snow boots alone during these colder months. And why should one deprive oneself of a robust boot season when there are so many types of boots out there? You got your rain boots, Chelsea boots, duck boots, Timberland boots, combat boots, knee-high boots, over-the-knee boots; really, there’s a boot for everyone. This winter, I’m thinking of trying a boot I’ve never tried before. Just to shake things up a bit here over the holidays and into the new year, she’s thinking of stepping out in cowboy boots!

I know it’s a shocker that there’s a shoe I haven’t at least tried on, but it’s true. I know, I’m a fabulous, stylishly adventurous, thriving 40-something-year-old woman, and I’ve never worn cowboy boots; hard to imagine! Well, I’ve been seeing cowboy boots popping up in trend forecasts, magazines, and online, and I’ve noticed that western boots have taken on new forms, shapes, and colors. Plus, there are so many ways to style cowboys; they’re not just for jeans and work shirts anymore. Here are a few pairs I’m considering and what to wear with them.

First, the Coconuts Telluride Western Cowboy Boot from DSW in taupe and ivory is a neutral two-toned, classically embroidered pair with a 2.5” slanted stacked heel. Going with a more minimalist color allows for more versatility in the styling. A lighter, as opposed to a darker pair, can bring a bit of vibrancy to an otherwise standard outfit. A starkly toned western boot is also a great complement to holiday outfitting. I can see a pair like this with a corduroy skirt and a festive sweater. Or, to contrast, an all-black look of leggings and a turtleneck topped with a long dress coat.

Next are the Leena Cowboy Boots from Urban Outfitters that have more of a hipster vibe, with the dark green color and a mid-calf shaft. This pair can be worn with a cropped wool trouser or a plaid or tweedy pant paired with a blouse and blazer to create a bit of contrast in a workwear look. For something more casual, you could tuck in a slouchy pant leg, then layer a striped tee and cardigan to give a weekend look a bit of cowboy twist.

For a more traditional take, there are the Heritage R Toe StretchFit boots from Ariat rendered in full-grain leather with beautiful stitching that come in classic colors of distressed brown, black deer tan, or rosy red. Play off the rugged style of a more traditional boot and wear it with something flirty and feminine. A floral maxi dress with tights is a fun contrast to the menswear-inspired western boot, and you can lean into the western feel with a shearling suede style coat to keep toasty and look lovely. Or wear this boot like you would knee-high boots with skinny jeans or above-the-knee skirts and dresses.

On the flip side of tradition is the Public Desire Rodeo Ruched Cowboy boot available on Asos. This graphic, black and white, knee-high shoe definitely makes a statement with its wing-like emborder shaft and higher heel. Even though it’s named for the rodeo, these are not the boots to go mucking about the stock pens. Instead, play up the edgy aesthetic with faux-leather pants, a long-sleeved fitted tee, or bodysuit topped with a plaid shacket or blanket-style coat.

These are just four of the boots that have piqued my interest for the winter. There are so many great versions of cowboy boots out there in various colors, materials, and heights. Whether you are traditional or more modern, western style boots are versatile enough to pair with everything from dresses to jeans to trousers and slouchy sweaters in the colder months ahead. Yeehaw!