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Brown boots are having a moment again, and honestly, they never should've left. There's something about pulling on a good pair of tall boots when the air finally cools down that just feels like fall clicked into place. If your boots have been sitting in the closet since spring, consider this your sign to bring them back out, because I've got 18 ways to wear them that don't involve the same skinny jeans and sweater combo you've done a hundred times.
Skirts That Play Well With Brown Boots
A skirt and boots combo is basically the backbone of fall dressing, and this year the skirts themselves are doing more of the talking.
1. Plaid mini skirt, cream sweater, tall chestnut boots.
A plaid mini in a rust and camel colorway paired with an oversized cream sweater keeps this one feeling collegiate without trying too hard. Tuck the sweater in loosely, don't overthink it.
2. Tan midi skirt, ivory sweater, tall cognac boots.
This one leans elevated. A column midi skirt in warm tan with a fitted ivory sweater and cognac boots reads polished enough for a coffee date or a work-from-anywhere afternoon.
3. Leopard mini skirt, chunky knit, espresso ankle boots.
Leopard print is one of those prints that somehow reads neutral, and pairing it with a deep espresso ankle boot and a chunky oatmeal knit keeps the whole look grounded instead of loud.
4. Corduroy button-front skirt, burnt sienna sweater, espresso ankle boots.
Corduroy is back in a big way this fall. A button-front cord skirt in camel with a burnt sienna sweater on top and espresso ankle boots underneath is the kind of outfit that photographs well against actual falling leaves, not just Pinterest ones.
Denim and Brown Boots, Reworked
Denim and boots is the easiest pairing there is, IMO, but the details make it feel new.
5. Wide-leg dark wash denim, cropped moto jacket, chestnut ankle boots.
Wide-leg denim tucked into ankle boots creates a silhouette that's flattering on basically everyone. Add a cropped moto jacket in a warm brown, not black, and the whole thing feels less predictable.
6. Straight-leg jeans, teddy coat, tall cognac boots.
A teddy coat in camel over straight jeans and tall cognac boots is giving cozy without giving sloppy. This is your errand-day outfit that still looks intentional.
7. Boyfriend jeans, oversized blazer, chestnut ankle boots.
Relaxed boyfriend jeans with an oversized blazer in a deep plum or espresso tone and ankle boots strikes that off-duty-but-put-together balance perfectly.
8. Wide-leg jeans, cropped cardigan, tall chestnut boots.
Wide-leg denim tucked into tall boots with a cropped rust-colored cardigan layered over a fitted tank keeps things relaxed but still shows off the boot. It's the kind of outfit you throw on when you want to look like you tried without actually trying.
Dresses Made for Boot Season
Don't put the dresses away just because it's cold. Layer them.
9. Rugby-style collared dress, tall cognac boots.
A collared, oversized dress with a varsity feel paired with tall cognac boots is unexpectedly one of the chicest combos out there right now. Add a crossbody bag and you're done.
10. Floral wrap dress, leather jacket, espresso ankle boots.
A wrap dress in a deep burgundy floral with a black or espresso leather jacket thrown over it and ankle boots underneath takes a summer piece straight into fall territory.
11. Sweater dress, tall chestnut boots.
A ribbed sweater dress in a rich plum or espresso shade with tall boots is basically a one-and-done outfit. Minimal effort, maximum payoff.
Trousers and Leggings, Elevated
12. Black leggings, oversized cinnamon sweater, espresso Chelsea boots.
Leggings get a bad rap for being lazy, but an oversized sweater in a warm cinnamon tone and Chelsea boots turns this into an actual outfit, not just loungewear that left the house.
13. Wide-leg trousers, fitted turtleneck, chestnut ankle boots.
Wide-leg trousers in a deep olive or espresso with a fitted turtleneck and ankle boots is a look that works for nearly any setting, IMO the most versatile combo on this whole list.
14. Cropped straight-leg pants, knee-high chestnut boots.
Cropped pants show off the boot, which is honestly the whole point some days. Keep the top simple so the boots stay the star.
Outerwear-Forward Looks
15. Long wool coat, ribbed turtleneck, tall chestnut boots.
A camel or espresso wool coat over a fitted turtleneck with tall boots underneath is effortless in the way that actually takes a little effort to plan.
16. Trench coat, dark denim, cognac ankle boots.
A trench in a deeper caramel tone (not the classic beige everyone already owns) paired with dark denim and ankle boots feels fresh without straying too far from the classic formula.
Polished Enough for the Office
17. Blazer, tailored trousers, chestnut boots.
A structured blazer in deep plum or espresso with tailored trousers and boots is proof that boots don't have to be casual. This one goes straight from desk to dinner.
18. Sweater vest, button-down, burgundy corduroy mini skirt, cognac boots.
Layer a sweater vest over a button-down, add a burgundy corduroy mini, and finish with cognac boots. It's giving preppy, but the rich colorway keeps it from feeling costume-y.
Brown boots are one of those investments that pay off every single fall, and this season's color palette (think chestnut, cognac, and espresso instead of a flat tan) makes them easier than ever to style. Pick two or three combos from this list, build the rest of your closet around them, and you've basically solved fall dressing before September even starts.
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