25 Trendy Fall Outfits with Boots to Try This Season

Fall is the perfect time to showcase your favorite boots. From knee-highs to ankle boots, they’re a versatile and stylish choice for cooler weather. To help you make the most of your boots this season, here are 25 trendy fall outfits that pair perfectly with them.

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1. Chunky Knit Sweater and Leather Leggings

Pair a cozy chunky knit sweater with black leather leggings for an edgy, yet comfortable look. Add knee-high boots with a chunky heel or ankle boots to complete the outfit. Opt for a crossbody bag and simple jewelry to keep it chic.

2. Plaid Mini Skirt and Over-the-Knee Boots

A plaid mini skirt paired with over-the-knee boots creates a stylish, preppy look. Choose a high-waisted skirt and a fitted turtleneck or sweater. Add a pair of opaque tights and a structured handbag to finish the look.

3. Sweater Dress and Ankle Boots

A sweater dress is both cozy and chic. Opt for a long-sleeve sweater dress in a fall color and pair it with ankle boots. Add a belt to cinch the waist and accessorize with a statement necklace or scarf.

4. High-Waisted Jeans and Combat Boots

High-waisted jeans paired with combat boots create a trendy, casual look. Choose a pair of slim-fit jeans and a relaxed sweater or graphic tee. Add a bomber jacket for extra style and warmth.

5. Midi Dress and Knee-High Boots

A midi dress is perfect for fall. Opt for a floral or patterned dress with long sleeves and pair it with knee-high boots. Add a leather jacket for an added layer of warmth and a touch of edge.

6. Turtleneck Sweater and Corduroy Skirt

Pair a fitted turtleneck sweater with a corduroy mini skirt for a retro-inspired look. Add knee-high or over-the-knee boots and a pair of tights if needed. Complete the outfit with a crossbody bag and gold jewelry.

7. Button-Down Shirt Dress and Ankle Boots

A button-down shirt dress is versatile and perfect for fall. Choose one in a plaid or solid color and pair with ankle boots. Add a belt to define the waist and accessorize with a simple clutch or crossbody bag.

8. Denim Jacket and Midi Skirt

Layer a denim jacket over a midi skirt for a casual, layered look. Pair with knee-high boots or heeled ankle boots. Choose a flowy skirt and a fitted top for a balanced silhouette. Finish with a crossbody bag and minimal jewelry.

9. Shacket and Skinny Jeans

A shacket (shirt jacket) paired with skinny jeans is perfect for fall. Choose a shacket in a plaid or neutral color and add heeled ankle boots. Complete the outfit with a structured handbag and layered necklaces.

10. Poncho and Over-the-Knee Boots

A poncho is a stylish and cozy option for fall. Opt for a poncho in a neutral or autumnal color and pair with over-the-knee boots. Add skinny jeans or leggings for a comfortable, chic look.

11. Maxi Dress and Ankle Boots

A flowy maxi dress works well in fall when paired with ankle boots. Choose a dress with long sleeves or a high neckline. Add a belt to cinch the waist and accessorize with a wide-brim hat and a matching clutch.

12. High-Waisted Trousers and Knee-High Boots

Pair high-waisted trousers with knee-high boots for a polished, sophisticated look. Opt for a tailored blazer or a fitted sweater and add a leather handbag. Simple jewelry will complete this elegant outfit.

13. Layered Sweater and Mini Skirt

A layered sweater over a mini skirt creates a trendy fall outfit. Choose a sweater with a high neckline and pair it with a plaid or solid mini skirt. Add knee-high boots and a structured handbag.

14. Sweater Vest and Wide-Leg Pants

Pair a sweater vest with wide-leg pants for a stylish and comfortable look. Choose a fitted turtleneck or long-sleeve shirt under the vest. Add heeled ankle boots and a matching handbag for a chic finish.

15. Leather Skirt and Fitted Top

A leather skirt paired with a fitted top is a bold, fashionable choice. Opt for a midi or mini leather skirt and a turtleneck or long-sleeve top. Add knee-high boots and a crossbody bag to complete the look.

16. Cardigan and Skinny Jeans

Layer a long cardigan over a fitted top and skinny jeans for a relaxed, cozy outfit. Pair with ankle boots and a matching handbag. Simple jewelry and a beanie will add a stylish touch.

17. Cape Coat and Ankle Boots

A cape coat adds a dramatic flair to any fall outfit. Pair it with a simple dress or fitted top and skinny jeans. Add ankle boots and a crossbody bag to complete the look.

18. Hoodie Dress and Combat Boots

A hoodie dress is perfect for a casual, comfy fall outfit. Choose a hoodie dress in a neutral or fall color and pair with combat boots. Add a beanie and a backpack for a laid-back vibe.

19. Blazer and Trousers

Pair a tailored blazer with matching trousers for a chic, office-ready look. Opt for a fitted blouse or turtleneck underneath and add heeled ankle boots. A structured handbag and simple jewelry will finish the outfit.

20. Flannel Shirt and Denim Skirt

A flannel shirt paired with a denim skirt creates a casual, autumnal outfit. Choose a high-waisted denim skirt and add knee-high boots. Accessorize with a beanie and a crossbody bag.

21. Cozy Sweater and Faux Leather Pants

A cozy sweater paired with faux leather pants is perfect for a stylish fall look. Choose a relaxed sweater and add heeled ankle boots. Complete the outfit with a crossbody bag and layered necklaces.

22. Poncho and Skinny Jeans

Layer a poncho over skinny jeans for a cozy, stylish outfit. Choose a poncho in a neutral or autumnal color and add heeled ankle boots. Accessorize with a beanie and a small handbag.

23. Turtleneck and Pleated Skirt

A fitted turtleneck paired with a pleated skirt creates a chic, feminine look. Opt for a high-waisted skirt and add knee-high boots. Accessorize with a structured handbag and minimalistic jewelry.

24. Oversized Sweater and Leggings

An oversized sweater paired with leggings is a comfortable yet stylish option. Choose a cozy sweater in a fall color and add knee-high boots. Complete the look with a crossbody bag and simple jewelry.

25. Plaid Pants and Turtleneck

Plaid pants paired with a fitted turtleneck create a trendy, sophisticated outfit. Opt for high-waisted plaid pants and add heeled ankle boots. Complete the look with a structured handbag and gold jewelry.

Styling Tips for Fall Outfits with Boots

When putting together your fall outfits with boots, keep these styling tips in mind to ensure you look both stylish and comfortable:

1. Mix and Match Textures: Fall is a great time to play with textures. Combine cozy knits, leather, and denim for a fashionable and comfortable look.
2. Play with Proportions: Pair fitted tops with flared or wide-leg bottoms, and vice versa, to create balanced and flattering outfits.
3. Layer Wisely: Layering adds depth and warmth to your outfit. Combine sweaters, cardigans, and jackets for a stylish and practical fall look.
4. Accessorize Thoughtfully: Accessories like scarves, hats, and jewelry can enhance your outfit. Choose pieces that complement your look without overwhelming it.
5. Consider Comfort: Ensure that your boots are comfortable for extended wear, especially if you’ll be standing or walking a lot. Opt for cushioned soles and manageable heels.
6. Choose Fall Colors: Incorporate fall colors like burgundy, mustard, forest green, and burnt orange into your outfits for a seasonal touch.

By incorporating these outfit ideas and styling tips, you’ll be ready to step out in style this fall. Whether you prefer classic elegance or trendy sophistication, there’s an outfit here to suit every occasion and personal style. Enjoy the season and make the most of your favorite boots!