11 Fall Outfits with Boots: Perfect Pairings for the Season (2025 Edition)
Fall Outfits with Boots When the leaves start turning and the air turns crisp, there’s one thing every fashion-forward woman looks forward to: boot season. Whether you’re reaching for sleek ankle boots, chunky platforms, or thigh-high stunners, fall is the perfect time to step up your layering game and your footwear.
This 2025 edition rounds up 11 fall outfit ideas featuring boots, covering everything from casual campus strolls to chic city layering and countryside escapes. Think wearable, versatile, and full of personality all paired flawlessly with the right boot.
1. Turtleneck Midi Dress + Knee-High Boots
A ribbed turtleneck midi dress in taupe or chocolate hugs your silhouette while keeping things cozy. Style with classic knee-high leather boots and a wool coat draped over the shoulders for an elegant, no-fuss look.
Perfect for: Office days or city coffee runs.
2. Oversized Blazer + Mini Skirt + Chunky Ankle Boots
Tap into preppy-meets-edgy with a plaid blazer layered over a neutral knit and mini skirt. Pair with chunky ankle boots and scrunched socks peeking out for that effortless cool-girl vibe.
Perfect for: College campuses or art museum visits.
3. Leather Jacket + Knit Dress + Combat Boots
Balance softness with structure. A cozy knit mini dress gets toughened up with a cropped leather jacket and black lace-up combat boots.
Perfect for: Night strolls or rooftop dinner plans.
4. Shacket + Graphic Tee + Chelsea Boots
Throw a plaid shacket over a band tee and pair with black leggings or skinny jeans. Slide into sleek Chelsea boots for a versatile, low-effort look.
Perfect for: Pumpkin patches or bookstore dates.
5. Sweater Vest + Wide-Leg Jeans + Western Boots
Give your fall style a countryside twist. Pair a chunky sweater vest with wide-leg jeans and embroidered Western boots.
Perfect for: Farmers markets or vintage road trips.
6. Coatigan + Joggers + Lug Sole Boots
A coatigan (coat-cardigan hybrid) layered over a cropped hoodie and matching joggers creates elevated loungewear. Lug sole boots bring in texture and durability.
Perfect for: Lazy weekends or errands with edge.
7. Mock Neck Top + Pleated Skirt + Sock Boots
Create clean lines with a fitted mock neck top tucked into a flowy pleated midi. Add sock boots with a stiletto heel for polish.
Perfect for: Brunch, book signings, or gallery visits.
8. Oversized Knit + Biker Shorts + Ankle Boots
Comfort meets fashion. Oversized cable-knit sweaters over biker shorts with pointed-toe ankle boots create that off-duty model feel.
Perfect for: Casual city strolls or coffee catchups.
9. Long Trench Coat + Slip Dress + Heeled Boots
Style contrast is key: a silky slip dress underneath a structured trench, cinched at the waist with a belt. Add heeled leather boots to lengthen the silhouette.
Perfect for: Date nights or stylish commutes.
10. Teddy Coat + Straight Jeans + Platform Boots
Stay warm and playful with a teddy coat, distressed straight-leg jeans, and chunky platform boots. Add a beanie or baker boy cap for extra flair.
Perfect for: Flea markets or hot cider walks.
11. Sweatshirt Dress + Over-the-Knee Boots
Throw on a cozy oversized sweatshirt dress and pair it with sleek over-the-knee boots. Add a mini crossbody and you’re golden.
Perfect for: Travel days or shopping sprees.
