Confession from a shopping editor who’s spent over eight years in the fashion industry: Come winter, I’d rather live in a sweat set and UGGs every single day than throw on something objectively presentable. Sadly, my style-obsessed conscience won’t let me get away with that, which means I actually have to think through cold-weather outfits. As someone with a street-style aesthetic, who gravitates toward oversized bottoms, I’ve been zeroing in on baggy pants-and-boots outfits—aka the most practical solution for what I already own. The goal? Looks like a walking Pinterest Pin and has no skin exposed in New York City’s brutally cold temps.
But beyond practicality, loose-fitting pants and boots are a natural pairing simply because they’re so versatile. You can let the boots peek out from beneath the hem for a subtle vibe, or—my personal favorite—tuck the pant legs into the boots for a cooler, more intentional style that lets both pieces shine. Either way, it’s a foolproof formula that’ll easily make you look so much more put-together with minimal effort. Now, I’ll let these 11 baggy pants-and-boots outfit inspo pics do the talking.
Cropped jeans and studded boots
With cropped jeans, you take the guesswork out of styling boots—aka you don’t have to decide whether to hide them or tuck them in. I love the edgy, Y2K energy here, and it’s the metal details and the cohesiveness of the dark hues with different textures that really make it pop: studded boots, a chunky chain, and a grommet belt all come together for that rocker-chic vibe.
High-waisted tailored pants and suede knee-high boots
When I think of trousers, my mind usually goes straight to office-siren heels or loafers—very corporate, very conference room. But this camel monochrome moment has me rethinking everything. It still carries that powerful, businesswoman energy, yet feels equally at home on a runway. The contrast between the structured tailoring and soft suede creates an elevated juxtaposition that makes the whole look fresh.
Light-wash jeans and square-toe boots
A chunky square-toe boot adds a rugged, utilitarian edge that stands out against soft, faded denim. Lean into the relaxed vibe with an oversized knit sweater and jacket, or sharpen the look with a fitted top and cropped cardigan.
Corduroy pants and shiny, burgundy boots
Now this is what I call texture mixing done right. The tactile feel of corduroy paired with sleek boots proves that opposites really do work together. Don’t be afraid to play with color and pattern, too, to really take it up a notch!
Utility pants and slouchy boots
In my head, utility pants warrant sneakers or chunky combat boots. But this slouchy-boot moment? I’m into it. It softens the look and dresses things up just enough, while still keeping that laid-back look intact.
Satin cargo pants and stiletto boots
Long live the sexy stiletto boot! The sharp, slightly witchy heel peeking out from wide-leg satin cargos is such a power move. It’s an unconventional combo I can’t get enough of.
Dark denim jeans and lace-up combat boots
Proportion is doing the work here. The oversized denim tucked into lace-up, knee-high boots makes a statement, while a collared shirt, graphic sweater, and leather jacket ground the look.
White pants and split-toe block boots
Split-toe shoes have been everywhere lately (shout-out to the OG, Maison Margiela), and they always make a statement no matter how you style them. I’m loving how they peek out from under wide white pants—they still command attention without stealing the spotlight.
Wide-legged denim jeans and western boots
This mash-up of aesthetics has my full attention. It’s giving urban, downtown cowboy core—low-slung jeans, a hoodie, and a puffer vest styled with giant sunglasses and western boots. It’s out there in the best way and a combo I didn’t know I needed.
Pinstripe pants and pointed-toe boots
Lately, I’ve been loving the trend of mixing stripes. Pairing roomy pinstripe pants with a bright, horizontally striped button-up—and finishing with pointed-toe boots—brings a fresh twist to a classic power outfit.
Cropped silk trousers and snake-print boots
Personally, I’ve always seen silk trousers as lingerie-adjacent but totally public-friendly—the fabric keeps them flirty and light, yet completely polished. Pair them with snake-print boots, and the personality factor goes through the roof. I’m obsessed!
Megan Uy is an associate shopping editor at Cosmopolitan, where she searches for the best products in all things fashion, home, beauty, sex, gifts, and more, so you don’t have to. When she’s not writing for the site, she’s whipping up some cool and trendy content for the fashion section of the print magazine. She’s been with the brand since 2019 (when she was an itty-bitty editorial fellow), and she’s also written for Delish, House Beautiful, and People. Follow her on Instagram to get some BTS of the editor life and chaotic NYC content. Also, feel free to hit her up if you ever wanna discuss the madness that is TikTok.
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