20 Fall Outfits with Boots Perfect Pairings for the Season 2026

Boot season is here, Fall Outfits with Boots Perfect Pairings and it’s time to enjoy wearing boots without sweaty feet. A fashion stylist shares stylish fall outfits focused on boots. Working with a group of fashion lovers, they created a list of boot looks that range from ankle boots to over-the-knee styles. These outfits are made to be fun, trendy, and perfect for fall.

1. Classic Jeans and Ankle Boots

Wearing skinny jeans with sleek ankle boots creates a simple but stylish outfit. It’s perfect for everyday wear or a trip to the pumpkin patch.

2. Sweater Dress and Knee-High Boots

Wearing a sweater dress with knee-high boots gives a relaxed “I woke up like this” look. It helps you look put-together while still feeling like you’re in pajamas.

3. Leather Jacket and Combat Boots

This edgy outfit gives you a rock star vibe. It might even make you feel like starting a garage band.

4. Midi Skirt and Ankle Boots

This outfit shows that boots can be feminine too. It’s so pretty that even the falling leaves would be jealous.

5. Oversized Blazer and Chelsea Boots

This outfit looks polished on top and fun with the boots. It gives the vibe that you have your life together, even if your place is a mess.

6. Maxi Dress and Cowboy Boots

This boho-chic outfit is great for fall days when you can’t decide between a flower child or a cowgirl vibe. It mixes both styles in a fun and stylish way.

7. Leggings and Over-the-Knee Boots

This outfit is for when you want to be comfortable but still look ready to star in a music video.

8. Denim Skirt and Ankle Boots

This retro outfit brings back a sexy 90s vibe. It’s so nostalgic that it might make you start quoting “Friends.”

9. Plaid Shirt and Hiking Boots

This outfit is for when you want to look ready for a hike, but you’re really just heading to the coffee shop.

10. Slip Dress and Combat Boots

This outfit mixes grunge and glam styles. It’s edgy and stylish—Kurt Cobain would be proud.

11. Corduroy Pants and Chelsea Boots

Wearing corduroy creates a 70s-inspired outfit. It’s stylish and nostalgic enough to make you feel groovy.

12. Sweater and Slouchy Boots

This outfit is perfect for days when you want to look like you’re starring in a rom-com, cozying up in a cute reading nook.

13. Leather Pants and Ankle Boots

Wearing dainty florals with tough boots creates a look that’s both soft and strong, showing off your mix of styles.

15. Jumpsuit and Ankle Boots

Wearing a stylish one-piece outfit with statement shoes creates a bold, fashionable look—like a superhero costume for everyday life.

16. Trench Coat and Rain Boots

This outfit is perfect for unpredictable weather. It keeps you stylish while you splash through puddles.

17. Midi Sweater Dress and Knee-High Boots

This sleek and chic outfit creates a sophisticated, standout look without needing to say a word.

18. Cargo Pants and Combat Boots

This outfit channels a Lara Croft–inspired, adventure-ready vibe. Tomb raiding is optional, but looking fabulous is a must.

19. Turtleneck Sweater and Over-the-Knee Boots

This outfit gives a sexy librarian vibe while keeping you warm on chilly days.

20. Joggers and Sneaker Boots

This outfit looks like you’re heading to the gym, but is perfect for Netflix and chill instead. Altogether, these twenty fall outfits are fun, stylish, and perfect for expressing yourself. Mix, match, and strut your stuff like the autumn queen you are—after all, if the boots fit, wear ’em!