29 Super Chic Fall Outfits With Boots

By: Avatar photo Andy Jones Updated: Mar 10, 2024


Fall is such a beautiful time of year and you can reflect that beauty wearing fall outfits with boots that will certainly draw their attention. From the sweet ankle boots to the daring thigh high leather styles, they will know you are a seasonal fashionista when you appear in these fall flavored designs. Sweaters, jackets, jeans, leggings, and dresses can be mixed and matched to create fall outfits with boots that give you a twinkle in your eye and a swing in your step. Check out these looks that will make them fall for you.

Fall Into Style With These 29 Booted Beauties

29 Super Chic Fall Outfits With Boots

1. Steppin’ Out Black Ankle Boot Outfit

This should be one of your fall outfits with boots. By having a block high heel design, these cute boots will dress up any pair of pants or jeans. The black jacket can keep you styling while you stroll down the avenue. Oh yes, did I mention this outfit will put a swing in your step?

2. Riding High Knee Pull-On Boot Ensemble

A classic knee length riding boot that will add to this work or play outfit without breaking stride. This late season ensemble has it all including skirt, scarf, jacket, and handbag. You don’t need to be a horse lover to find these wardrobe pieces in your closet.

3. Grand Dame Knee High Boots Apparel

You will be thought of royally when you go out wearing these knee high beauties. Wear this flirty dress and boot combo anytime you feel the need for a little bowing and hand kissing.

4. Take The Platform Black Boots Outfit

You will dominate any social scene when you wear these gorgeous thigh-high, pull-on, tall heel, platform boots over jeans. This bold plaid top just pulls them to you. Everyone will succumb to your wishes where ever you go in this fun outfit.

5. Dress-It-Up Knee Boot Ensemble

Source: zappos.com

A knee boot ensemble that will dress you up any day for an either work or casual outing. Take note that you will want this pair of boots as a wardrobe staple. This long sleeve, flirty, above the knee dress should be a day or night staple also.

6. Here Kitty-Kitty Thigh Highs Weekender

These sweet thigh high boot may look innocent but they can evoke the tigress in you. Yet, they are just purrfect for your fall outfit with boots when wanting to cat- around. This weekender set will look good anywhere.

7. Welly-Done All Weather Boot Outfit

Source: amazon.com

You need an all season Wellington style rain boot will keep your toes nice and dry in rain or snow. A must have for days that are not all sunny and bright. This layered look will keep you looking good and feeling warm during the fall’s darker days.

8. Tally Ho Knee Riding Boot Ensemble

Source: bmodish.com

Let the hunt begin when wearing this low heel riding boot with a top strap accent. It doesn’t matter what you are hunting for, this boot and jeans ensemble will meet the challenge. Long layered hair is a fantastic choice for this look.

9. Walkin’ The Beat Over The Knee Boot Look

Source: debiflue.com

This black over the knee low heel boot will let you trek wherever you want to go in style. Let’s get that sweater and flirty skirt on and go shopping.

10. Dressy Black Delight Heeled Boot Outfit

Your fall dress outfit is not complete without a flirty pair of mid-calf boots to give it an extra flair. Time to shine while on the go!

11. For Gray Days Knee Boot Ensemble

Take the chill off when outfitted with these gray knee high boots and woven tunic sweater. Add the large carry-all bag to carry anything.

12. On The Go In Early Snow Apparel

These knee high boots will keep your legs warm when wearing this sweater over blouse layered look with jeans. So bring on that early first snow.

13. Cape Nod Thigh High Boot Outfit

And nod they will, when you appear in this black thigh boots over jeans with this fabulous buckle closure cape. Humility can be a challenge at times.

14. Looking For Studs Riding Boot Ensemble

Source: polyvore.com

These studded riding boots are the focal point of this sweater and jeans ensemble. Even the lovely accessories won’t distract from these classy boots. Plan on getting some attention when you step out to run your errands.

15. In A Furry With Thigh Highs

What a fall statement you will make in these sexy disappearing thigh high boots and lovely tunic multi-fur jacket vest. They may just try to make you let them rub you the right way.

16. Continuous Rad Knee Boot Outfit

They will know just how fun you are when you appear in these knee high boots and continuous plaid scarf. The cable knit sweater and jeans are a great back drop to complete this outfit.

17. Not a Rote Coat With Knee Boots

Source: hapatime.com

These over the knee boots set the stage for this great green light weight coat with a basic black dress. You are ready for office or class looking classy and casual at the same time.

18. Keepin’ The Chill Off Tall Boots Outfit

Time to put on these over the knee boots and this lovely tan coat when the fall winds begin to blow. The wrap skirt just adds a bit of tease when the winds begin to kick up.

19. Sock It To Me Dressy Boots

Source: zappos.com

Knee high boots with a tease of socks showing just lends itself to the asymmetrical hem on this flirty little dress. This outfit is warm and a winner.

20. Steal Your Heart Pirate Boot Ensemble

Source: noholita.fr

Take no prisoners when wearing these laced-top thigh highs with a mini skirt and bulky knit sweater. You will look like a million dollars as you steal the hearts around you.

21. Take It To The Bank Ankle Boot Outfit

This is no risk, sure to win, attention-getter garb with a leather and fur focus. From the ankle boots to the sleeveless tunic sweater jacket, this says you are ready for fall.

22. Collar And Cuff Thigh High Togs

Just being warm is not enough when you select this fall outfit featuring thigh high boots with a sleeveless collared jacket and cuffed woven sweater. You can add “provocative” to this look.

23. Classy And Sassy Hat To Boot Ensemble

They will know this is not your first fashion rodeo when you step out in this head to toe fashion eye candy treat. Knee high riding boots and a wide brim hat encase the plaid scarf and “down under” style riding coat.

24. That’s The Stuff Cuffed Boot Outfit

Time to fall into these over the knee cuffed boots that look great with leggings and a belted tunic sweater. The fall leaves are not the only attraction this time of year.

25. Glad It’s Plaid Tall Boot Wardrobe

Fall can’t start too soon to wear this navy short sleeve plaid top with leggings and over the knee gray boots. A great casual combo for shopping or school.

26. Waitin’ At The Station Booted Ensemble

You will be a welcome sight when you appear in this high neck sweater mini dress with thigh high boots and collared coat. It will make them want to come home more often.

27. Pretty As A Pea Boot Outfit

From the knee high leather boot to the sweet pea style jacket, you are dressed for a fall adventure as the leaves turn. It just keeps the look casual with the striped turtleneck and comfy jeans.

28. Tribal Fall Travel Booted Garb

Traveling in the fall can be so much fun while you look so chic in this tribal patterned jacket offset by handsome knee high leather boots. Basic black top and pants make this outfit POP!

29. Sweater Weather Thigh High Dress-Up

Woven mini sweater dresses are beautifully accented with thigh high leather boots and both will keep the fall chill at bay. Time to look forward to those upcoming shorter days.

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About the AuthorAvatar photo
Andy Jones

Andy focuses on getting readers familiar with the latest and trendiest hairstyles. There’s pretty much no style she has yet to try, and her mission is to help everyone find the perfect look they seek. When Andy is not gushing about hairstyles, she spends most of her time reading through her giant collection of sci-fi books or watching old Star Trek shows. See all articles from Andy.