How to Wear Ankle Boots and Booties: 100+ Outfits With Dresses & Jeans

Wondering what the ankle boot trends for women are this fall and winter? If so, look no further. We’ve gathered 33 of this season’s hottest new designer ankle booties from brands including Christian Louboutin and Giuseppe Zanotti.

Just in case you’re on a budget, we’ve included some inexpensive boots from ShoeDazzle and Amazon that you can buy from $9.99.

Scroll down to see what to wear and how celebrities style their ankle boots. Perhaps you’ll get some outfit ideas?

33 Women’s Ankle Boots From $10

Which of the following ankle booties would you like to add to your shoe collection?

1. Buckle Platform Ankle Boots, $64.99 at Public Desire

2. Black Peep Toe Chunky Platform Heels, $39.99 at CiciHot

3. Black Faux Suede Platform Booties, $38.99 at CiciHot

4. Badgley Mischka Meg Ankle Boots, $225 at Amazon

Pure elegance starts and ends with these Badgley Mischka booties featuring a metal overlay encrusted with crystals.

5. Mackenzie Rhinestone Booties, $10 at ShoeDazzle

Everywhere you go, go glam in ‘Mackenzie’. Use this mesmerizing style to add sparkle to a more neutral look, or add her to an already eccentric outfit to complete the ensemble.

6. Giuseppe Zanotti Roxie Ankle Boots, $1,250 at GZ Design

Design featuring an open toe, a high stiletto heel, a high ankle, a back cutout detail, a side zip fastening, a gold-tone buckle fastening, a contrast piped trim, a leather insole, and a leather sole.

7. Sky-High Sheba Ankle Booties, $10 at ShoeDazzle

Sheba is one ridiculously sexy bootie! Her sky-high silhouette is perfect for wearing for all those after-dark date nights and girls’ nights on the dance floor.

8. Lexi Velvet Booties in Navy and Bordeaux, $10 at ShoeDazzle

Velvet is the most luxurious part of fall footwear. Don’t miss out on the trend or on this stunning bootie!

9. Irena Ruffled Ankle Booties, $10 at ShoeDazzle

Irena is a total party girl. Wear this ruffled bootie with cocktail dresses, evening skinnies or tights.

10. Mackie Block Heel Booties, $10 at ShoeDazzle

Block heel booties are one of the most on-trend shoes you could own for fall. The thing is, they’re going to be everywhere, which is why we love Mackie for her amazing embellished details to help you really stand out.

11. Christian Louboutin Crochinetta Booties, $945 at Net-A-Porter and Nordstrom

“Crochinetta” is a svelte new booty this season. Featuring a strong pointed toe and a slender platform, this 100mm ankle boot in black leather is finished with elasticated paneling and a pull loop for a comfortable, slide-on fit.

12. Christian Louboutin May Wong Brocade Fur-Trim Booties, $945 at Bergdorf Goodman

“May Wong” brings Far Eastern beauty to your Fall/Winter wardrobe with an exquisite Chinese inspired floral jacquard and traditional tassel embellishment. This statement boot features a 100mm embossed velvet heel and is topped with the softest ultra rose orylag rabbit fur trim.

13. Passion Booties, $10 at ShoeDazzle

This sexy bootie has a lot to say! Choose the color and the phrase that speaks to you most. For us, they ALL do so we have one of each.

14. Aquazzura Shanty Tasseled Suede Ankle Boots, $1,115 at Net-A-Porter

Aquazzura’s ‘Shanty’ boots have been made in Italy from buttery soft suede and are gathered at the ankle for a slouchy paper bag effect. They’re detailed with cording along with the tasseled ties and have a sharp almond toe.

15. Flashy Imogen Stiletto Booties, $10 at JustFab

Channel your inner ’80s girl with these party-ready stiletto booties featuring a flashy, shiny finish, inner zip closure, and pointed toe.

16. Uber-Fierce Carlita Booties, $10 at JustFab

Strut like it’s nobody’s business in these uber-fierce stiletto booties featuring a lace-up front and inner zip closure.

17. Bijou Diamante Embellished Ankle Boots, $74.99 at Public Desire

Shine bright baes and make a serious statement in these diamante embellished ankle boots. Featuring pointed toe and stiletto heel.

18. Robbi Metal Ring Ankle Boots, $59.99 at Public Desire

Cause a stir in these no so plain Jane ankle boots. Featuring almond-shaped toe, metal ring detail, and block heel.

19. Ellery Velvet Ankle Boots, $1, 765 at Net-A-Porter

Ellery’s statement ankle boots were featured on the label’s Fall ’17 runway. Crafted in Italy from opulent dark-purple velvet, this pair sits on a chunky, curved Perspex heel.

20. Gianvito Rossi Mesh and Patent-Leather Ankle Boots, $1,045 at Net-A-Porter

Gianvito Rossi’s ankle boots give the illusion of pumps teamed with fishnet socks – one of this season’s key trends. Made from sheer mesh, this point-toe pair is trimmed with glossy patent-leather and set on a 105mm stiletto heel.

21. Blue Sequin Peep Toe Calf Length Booties, $42.99 at CiciHot

Make major statements in this flashy pair featuring a sequin detailed material, calf-length, peep toe, single soles, side zipper for closure, and cushioned insoles.

22. Closed-Toe Lace-Up Boots, $29.99 – $40.99 at Amazon

23. Purple Lace-Up Boots, $36.89 – $37.89 at Amazon

24. Chunky Retro Ankle Boots, $36.99 at Amazon

25. Floral Lace Ankle Booties, $29.50 – $37.50 at Amazon

26. Knit Peep-Toe Heels, $55.99 at CiciHot

Keep your feet cozy in this hot style featuring knit material, peep toe cut, single soles, slip-on construction, and cushioned insoles.

27. Nelly Bernal Spotlight Open Peep Toe Glitter Booties, $79.00 – $109.99 at Amazon and eBay

Shine in style in these gorgeous glitter booties featuring a well-made upper covered in sparkling glitter, an open toe, a ruched but structured top, and a side zipper closure.

28. LOVE Moschino Studded Ankle Bootie Stiletto Heel, $350 at Zappos

Break bad in these fierce LOVE Moschino studded ankle booties.

29. Ava Skinny Heel Pointed Toe Sock Boots, $61.99 at Ego

30. Tan Lace Up Chain Strap Platform Booties, $9.99 at ACW

31. Jacquelyn Faux-Fur Hiker Booties, $10 at ShoeDazzle

32. Karina Bow Accent Booties, $10 at ShoeDazzle

With slight ruching detail at the ankle and that exaggerated bow detail, ‘Karina’ is one super feminine bootie. Wear her to give that perfect dose of pretty to a date night outfit.

33. Black Faux Leather Pointed Toe Studded Booties, $49.99 at CiciHot

Match these edgy booties with a leather jacket for the ultimate look!

Celebrities Show What to Wear With Ankle Boots

Considered more versatile than knee-high boots, not to mention thigh-high boots, the following celebrities will show you how to wear ankle boots with jeans, leggings, skirts, and dresses.