(The Shopping List)
10 Winter Boots That Elevate All Of My Leggings Outfits
Dress up your favorite winter basic.
As much as I pride myself on being the kind of girl who loves to get dressed up for all occasions, the reality of winter is that sometimes, I just can’t. I’m already not a morning person, but when it’s cold, dark, and my dry skin feels like it’s been through a winter freeze, I just want to be comfortable and warm— not wrestle with an outfit that requires effort. That’s when I reach for the one basic that makes getting dressed a no-brainer: leggings. They are undeniably practical, but can also feel pretty uninspired and unfitting for a fashion girl. I’ve thought long and hard about the different ways to make leggings feel less blah and more me, and how I can style them to look much cooler than they feel. And honestly, the answer is simple: a fabulous pair of boots.
While I'm all for boots year-round (huge fan of a summer boots situation), winter is of course the prime time for boot lovers and the easiest route to take in dressing up a leggings outfit. Let me explain. First of all, when slush and snow are involved, bulky pants that trail the ground just won’t cut it, and leggings tucked neatly into boots are an easy solution. Plus, boots cover a large portion of your calves, so instantly, they shift the focus away from the leggings and onto the statement footwear. A fabulous pair of boots can handle all the attention, so much so that the leggings aren’t even a passing thought — just a comfy and sleek complement.
Once I have the right boots — whether it’s knee-high, over-the-knee, riding, or a lug-sole ankle boot — the rest of my outfit comes together effortlessly. I’ll pair the look with a chunky oversized sweater for that après-ski chic style or slip into an extra-long fitted turtleneck with a belt layered over it for an elevated snow bunny look. For a more tailored vibe, I love adding a bold, oversized blazer and standout accessories to complete the outfit. Either way, you can top it all off with a beautiful statement coat. The trick is to keep the leggings as just a base layer and build out from there, ensuring the boots and other layers are the stars of the show.
So, if you’re like me and leggings are your winter uniform, the solution is simple: find the right boots. Ahead, I’ve rounded up 10 pairs that will instantly elevate your leggings outfits, making you look polished even when the snow is falling — or, you just can’t bother with putting on anything else — no excuse needed!
These Totême beauties are my go-to for elevating leggings outfits. The wide shaft silhouette beautifully conceals my leggings and allows the boots to take the lead, physically. The rich brown toned croc texture comes off a bit softer than a a black croc would, yet still neutral enough to go with everything. This style will make any outfit feel both sophisticated and on trend—even when wearing the most basic leggings.
I adore an animal print — whether snakeskin, leopard, or anything else — so a statement boot in any such pattern is a must-have. They’re ideal for making an otherwise simple, all-black outfit look effortlessly chic and thought out. Since a printed boot is a bit more fun and less of an everyday staple, I opt for more affordable options to stock my wardrobe with, like this striking pick from Zara.
These fluffy stompers are the epitome of snow bunny chic. With their faux fur trim and sleek white design, they instantly elevate any wintery leggings look, giving off the perfect après-ski vibes. They remind me of my mom's classic Tecnica boots that I borrow whenever I’m in Chicago. I love pairing the style with leggings, a fitted turtleneck, and a belt for that polished ski girl look that’s both cozy and effortlessly chic.
The Coperni Bridge Cowboy Boot takes western style and makes it modern. I’m obsessed with the sleek silhouette and extended pointed toe, which gives the boot a sophisticated and cool-girl edge. I’ve gotten so many compliments when wearing these, and they are an easy and ideal match for dressing up my leggings. They look fabulous when paired with a shearling-trimmed coat to create a winter-ready look. Very Aspen chic.
All of the Chloé boots were incredible this season, but this style is currently top of my wishlist. The wooden block heel adds more practicality for the cold-weather months, and an interesting contrast against the luxe leather. Plus, the rich burgundy hue is right on trend for winter 2025. The dramatic foldover top adds a unique touch and creates dimensions to the silhouette that looks great when paired with leggings.
By Far’s Stevie 42 boots are a must-have for everyone. When I bought my first pair, they were my biggest shoe splurge — but I’ve had them for years and have worn them more than any other boots I own. The silhouette is 10/10, the kitten heel is the perfect height for walking throughout day and night, and they comes in a variety of colors and textures so there is something for everyone. I’m eying this beautiful soft taupe pair to add to my collection. It’s a beautiful neutral tone, and will add a pop to my outfit when paired with black leggings. I’ll throw on a matching toned, oversized turtleneck sweater for an easy everyday look.
Over-the-knee boots can sometimes feel cheesy, but these Aeyde stunners are anything but. They offer a timeless, sophisticated take on the style, with a perfectly proportioned design that pairs beautifully with leggings. These boots will hide your leggings, yet effortlessly stand out no matter what else you wear them with, ensuring you look cool and elevated, without ever trying too hard.
Moon Boots are always a playful choice in snowy or icy weather. With their faux-fur trim, these boots also give off après-ski vibes, but in a sleek, modern way. They’re cozy and warm, and I love that I can throw them on with leggings and a puffer for a cool winter look that just feels fun. Whether I’m actually hitting the slopes or simply running errands in my neighborhood, these boots make me happy!
Moto meets western meets riding with these square-toe Mango boots. They’re a great pick for a more casual outfit when you are going to be running all over the place or stomping around the city in the cold-weather. They’ll look great when the weather warms up a bit too, paired with leggings and an oversized leather jacket.
Go big or go home, right? These Johanna Ortiz metallic leather boots are the coolest statement. Bold and quirky, wearing these gives off main character energy — even when paired with leggings! They’ll demand attention for all the right reasons.
