1. Dress and Cardigan

Source: 10 Ways to Style: Knit
This outfit can take you from school to your study group to hanging out with friends. The ankle boots are a nice change from heels, don't you think?

2. Crop Top Sweater and Flared Skirt

Source: Top 10 Ways How To
Now this is a really fun look for fall. The textured tights with the chunky booties will keep you warm while the skirt and sweater allows you to show off your girly side.

3. Leggings and a Military Jacket

Source: 10 Ways to Wear Ankle
Leggings are always a good choice on those days you just don't know what to wear. Tuck those leggings into your ankle boots, throw on a t-shirt and jacket, and off you go!

4. Coat and Khakis

Source: whowhatwera.com
Wear your ankle boots like a street style star and throw a coat over your shoulders and strike a pose!

5. Pencil Skirt and Cardigan

Source: An Ode to Pencil Skirts
The colors and textures of this look is SO fall. This very ladylike and smart look is perfect for class or work.

6. Plaid Scarf and Sweater

Source: 7 ways to style a
Fall accessories are the best. This scarf is so voluminous and really pulls the look together with the distressed denim and gray ankle boots.

7. Cuffed Denim and a Flowy Coat

Source: babble.com
Cuffed skinny jeans and ankle boots together are a must! This look is really balanced from the flowy coat to the slim jeans and boots.

8. Denim on Denim

Source: 17 Ways to Wear Boots
White jeans tucked into ankle boots with a t-shirt and chambray top can in fact work in fall. Swap the t-shirt for a sweater or wear a darker shade of chambray.

9. Plaid Dress

Source: Celebrity Style and Fashion Trend
Lots of great layers going on and the white booties add an unexpected touch.

10. Dark Skinnies and a Coat

Source: Celebrity Style and Fashion Trend
I'm in love with the neutral accessories paired with this black look. This shows that everything doesn't have to be super matchy-matchy to be stylish.

11. Cuffed Jeans and a Sweater

Source: 10 Ways to Wear Ankle
This look is pretty easy to recreate and love. The ankle boots take things up a notch so you look more polished than with sneakers and it looks comfy!

12. Boyfriend Jeans

Source: The One Staple We'd Wear
Jessica Alba paired her military jacket with distressed boyfriend jeans and heeled ankle boots.

13. Cardigan, Coat, and Skinny Jeans

Source: Top 10 Ways to Wear
If you're tired of brown or black boots, go for a daring red! This is another simple, comfy chic look for school or a football game.

14. Layered Top and Striped Skirt

Source: 20 Style Tips On How
Just because it's a little chilly out does't mean you have to put all your skirts away. Rock your skirt with a button-up blouse and sweatshirt and finish it off with ankle boots of course!

15. Belted Dress

Source: A Clothes Horse: Photographic Memory
Super cute look to welcome the fall season. Cinch your dress and cardigan with a vintage belt. Then, throw on some tights to keep your legs warm and ankle boots for a classic look.

16. White Button-up and Coated Denim

Source: 31 Pretty Fashion Images That
Style basics that are far from boring. Coated denim with a simple button-up is timelessly cool.

17. Cable Knit Tights and Skirt

Source: 8 Ways To Wear Tights
A short sleeved sweater, plaid skirt, and cable knit tights with heeled booties is ideal for all those fall outings.

18. Denim Jacket and Tank Dress

Source: Wendy's Lookbook
I know you can't see the dress, but Wendy Nguyen paired a black tank dress with suede ankle boots and a light denim jacket. It's perfect for those not too hot, not too cool days.

19. Frayed Denim and Striped Jacket

Source: Man Repeller
Mixing stripes with animal print? Yes! Channel your inner street style star by mixing prints with some frayed denim.

20. Dark Denim

Source: How to Master Bohemian Style
We've seen a lot of skinny jeans worn with ankle boots and I'm told an important part of the style is to show a sliver of skin to slim the ankles. Give it a try!

21. Long Sweater and Pencil Skirt

Source: How to Wear Ankle Boots
This sleek look plays with proportions. If it's not too cold out, bare those legs with a longer pencil skirt and ankle boots.

22. Floral Dress

Source: Pinterest
This is another fab look for when you want to look good in a hurry. A fun floral dress and ankle boots with some metal detail is polished and pretty.

23. Flowy Skirt and Long Coat

Source: Celebrity Style and Fashion Trend
Don't forget to experiment with fabrics and colors. This outfit combines great colors and textures with shiny, chunky- heeled boots.

24. Blazer and Belts

Source: Celebrity Style and Fashion Trend
I am in love with this gray blazer worn with belted ankle boots. You look like you mean business!

25. Slouchy Jacket and Beanie

Source: How to Master Bohemian Style
This look is so carefree and cool. Beanies are a fashion staple in the fall and winter and the slouchy jacket balances out the look.

26. Long Kimono Jacket and Crop Top

Source: How to do the Boho
So boho chic! For those warmer days, wear that crop top with a long kimono jacket and peep toe booties.

27. Flared Denim on Denim

Source: Celebrity Style and Fashion Trend
Ankle boots with flared denim is a nice break from the sea of skinny jeans. Don't be afraid to experiment with what you wear.

28. Oversized Coat and Cuffed Pants

Source: Celebrity Style and Fashion Trend
Cuffing your jeans or pants is a good alternative to tucking then in your boots. This shorter look with an oversized coat was made for street style stardom.

29. Fitted Denim Top and Skinny Jeans

Source: 15 Things Stylish Women Do
Short ankle boots, cuffed jeans, and a slim top is modern and perfect for running around town.

How do you like to wear your ankle boots? Do you have any style tips on how to wear them?