The Best Winter Boots to Complete Your Look

Shoes and Bags, Style Tips

Bobbi admires a spectacular pair of mid-calf Fendi combat boots.


In search of the perfect winter boot? Look no further!

Those of us who love winter, and all the looks of winter, know how the perfect boot can finish our look. If you’re searching for your perfect pair, you’re in luck. We’ve found some amazing winter boot options for you, and WOW, how much fun are they?! And in terms of keeping you warm, well, what we’ve found for you is definitely the ticket!


Style Overview…

As always, the tall boot is a big shot—and there are some truly gorgeous finds that work with everything from jeans to dresses. They are a staple that takes your look to stunning! And then there are the combat and lug sole boots—both fun and edgy ways to pull your casual looks together.

For dressier moments, you’ll want to keep in mind all the stunning looks you can put together wearing tall boots. A pointy-toe stiletto heel of any height creates a refined, slenderizing, body-lengthening look that will get you miles of chic. The pointy-toe ankle boots do the same, and you will be thrilled to see so many yummy options. And the flat boots you’ll see this season are simply gorgeous. You will see ankle to mid-calf to tall, and each pair is stunning and versatile.

From a practical standpoint, we are also serving up some cozy winter après ski boots. These are perfect for those of you traveling to ski or who simply want to be toasty warm in your footwear. We know you are going to love what you see here!

Since COVID, we have been starved for a wide selection of these treasures, so feast away on all you see here!

Pointy-toe Tall Boots & Ankle Boots—Timeless Treasures

Pointy-toe boots, whether they be knee-high, over-the-knee, ankle, or something in between, along with any of the heeled boots you see here, are both timeless and perfect worn with a wide variety of casual and dressy styles.

For example, you can wear tall boots for casual cocktail with a pair of skinny or wide-leg cropped jeans—or even leggings.

We show over-the-knee boots in a few styles, all of which are fabulous and easy to wear. I have even included a pair of low-heeled, satin, over-the-knee boots that you can wear in so many ways. A “WOW” for sure!

Flat Boots

Another divine style of boot is the flat boot. They are endlessly useful and timelessly chic. We feature options that are considered more classic (with a traditional flat heel), along with some options that are a bit more on the trendy side. Wear them with leggings, skinny jeans tucked in, skirts, and dresses. These are perfect for those who are fans of the flat boot.

We have found some stunning options in riding boots for you, so be sure to check them out. Buy well, and they will last a lifetime.

Après Ski Boots

Another fabulous category of winter boot is the après ski boot. Who doesn’t love their absolute coziness? They are a winter wardrobe must-have, whether you’re wearing them in the city or at a fabulous ski resort.

We have found an assortment of these cozy trending boots for you. Naturally, they are perfect worn with ski pants, and when in town, your skinny jeans will look fabulous worn with the taller options.

If you’re buying the ankle-height variety of this fabulous winter boot, please stay away from your skinny jeans and opt for wide-leg and flare-leg jeans instead. If you look around, you’ll see many options for these jean silhouettes this season.

FASHION ALERT! Please remember that you NEVER want to wear ankle boots of any kind with skinny jeans.

Combat & Lug Sole Boots

Combat and lug sole boots are a hot boot trend. They have been growing in popularity over the last few seasons, and for good reason—they are comfy, trendy, and fun to wear!

These showstoppers are perfect worn with flare-leg and wide-leg jeans unless you are doing the tall lug-soled boots. If you go that route, you can obviously wear them with leggings and skinny jeans and even the ever-so-current knit dresses. What a yummy, edgy combination.

Summing it All Up

Boots are an essential part of your winter wardrobe, and the treasures found here will get you through the season easily, chicly, and warmly.

As with your shoes, your boots will be the first and last thing people will note about what you are wearing. Remember that your footwear is always your first “tell” of chic when people check you out—often doing no more than looking to see how cute you look—and, as we all do, looking for ideas for ourselves. Do we want to copy? Maybe…

That said, selecting the perfect pair of boots to meet your needs is worth taking the time to do, so we urge you to take advantage of what we’ve found for you. Shopping will be a cinch, and your chic will be ensured.

Happy shopping, and remember, we are a mere email away. If you need any assistance, give us a shout at [email protected].

PSSST! Looking for more curated shopping? Check out some of our other recent posts!

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