Winter is here, and with it comes the usual conundrum of styling cute boots in volatile weather. In fact, discovering how to style brown boots with jeans for the season has become our highest priority. That’s because the unexpected summer and fall 2025 trend has carried over into winter 2026 and proven to be extremely versatile and wearable.
Yes, we know that chunky loafers are comfortable, black boots go with everything, and sneakers are the most reliable shoe in any season. But there’s something so enigmatic and intentional about wearing brown boots. Maybe it’s the “wrong shoe theory” at work, but they seem to strike the right balance between neutrality and drama.
They play especially well with another closet staple: denim. Not as soft as a beige loafer, nor as fierce as a black heel, brown boots provide a perfect middle ground that brings a defined silhouette and relaxed sophistication to your look.
Convinced? Here’s our advice on how to style brown boots with jeans this winter. These outfit ideas don’t have to remain with the cold weather, either. Once spring approaches, simply switch your wool overcoat to a blazer or a light jacket for the perfect transitional outfit.
With capri jeans, or extra-long jorts, brown boots can work as a visual counterbalance. Because the pants end above or just below the knee, leaving skin exposed, the boots help elongate the figure and dramatize the look. (And keep you warm in colder weather.) We recommend taller boots in a structured or cowboy style over ankle booties here for that reason. Keep the top light—like a favorite T-shirt or a romantic blouse—and layered over a classic turtleneck or button-down shirt. Choose a bag that’s as fun and playful as the rest of this brown boots outfit.
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The combo of a white top and jeans always looks crisp, and with dark brown boots the whole ensemble becomes a lesson in clean modernism. No frills here; just a well-executed look ideal for drinks, leisurely strolls through museums, and any other plans the weekend offers up. Add a suede jacket to further bring out the warm tones of the shoes.
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The volume of the baggy jean demands direction, and a brown suede boots can provide a visual anchor that prevents the outfit from totally overflowing. A simple white T-shirt, tank top, or turtleneck adds a necessary pause, while a structured bag and blazer offers a perfect contrast to the relaxed fit of the pants. This street-style-approved formula is all about balancing proportions.
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Straight-leg jeans are all about clean lines and effortless, uncomplicated attitude, and brown ankle boots feel like a natural fit with them. So it’s best to style both with similarly unfussy pieces, like a simple sweater or top and classic sunglasses. As for layering, the suede jacket trend works well here for an understated elegance that will fit in at creative offices, casual dinners, or anywhere that calls for poise without pretension.
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A classic denim dress is a wonderful base for a pair of tall knee-high boots. The leather boots add texture and drama to the timeless denim dress, and together they create a vibe that spans decades: It feels a little bit ’70s, a little bit ’90s, and a lot of now. It’s what we’d wear to a dinner that seems destined to end in a long night of drinks out.
Good style is often about creating tension, and combining a pair of brown boots with a jean skirt is a great example. While everyone else might run to the obvious winter outfits—black tights, black boots, miniskirt—wearing brown boots with a light blue maxiskirt feels more intentional and offers a casual elegance that is unmatched.
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Forget the “rule” that you can't mix brown with black. Style mocha ankle boots with black or gray skinny jeans for an unexpectedly chic combo. Keep the rest of the look minimal and focused to match the sleek aesthetic of your heeled boots. A gray crewneck sweater and black leather bag are all you truly need to look polished here.
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Is there anything as timeless as a pair of riding boots? Yes, a denim jacket! Together, the two are the perfect match to instantly elevate any outfit. It doesn’t matter what shade of brown the boots are—everything from chocolate brown to light caramel will work—just make sure to keep the accessories modern for a fresher approach to this classic ensemble.
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A version of this article was previously published in Glamour Mexico and Latin America.
