--- title: "29 Stylish Options to Rock Your Ankle Boots This Fall ..." description: "Dress and Cardigan; Crop Top Sweater and Flared Skirt; Leggings and a Military Jacket; Coat and Khakis; Pencil Skirt and Cardigan; More ..." url: "https://shoes.allwomenstalk.com/stylish-options-to-rock-your-ankle-boots-this-fall/" category: "shoes" last_updated: "2026-06-07" --- # 29 Stylish Options to Rock Your Ankle Boots This Fall ... Break out those ankle booties, it's time to start thinking about ways to style them for fall! I think ankle boots are a simple and stylish staple in any wardrobe. They're so chic and you can wear them so many different ways. Check out some of these trendy ways to wear ankle boots this season ## 1. Dress and Cardigan ![Dress and Cardigan](https://resize.allw.mn/1028x0/filters:format(webp)/filters:quality(70)/content/tq/u2/r6ijkrpy55ff6a2256fc1654353477_533x800.jpg) Source: [10 Ways to Style: Knit](https://goo.gl/HokWss) 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 ![Crop Top Sweater and Flared Skirt](https://resize.allw.mn/1028x0/filters:format(webp)/filters:quality(70)/content/tf/d3/svfhjzk055ff6a24303a2080106432_600x1538.jpg) Source: [Top 10 Ways How To](https://www.topinspired.com/how-to-wear-a-crop-top/) 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 ![Leggings and a Military Jacket](https://resize.allw.mn/1028x0/filters:format(webp)/filters:quality(70)/content/pn/ov/mkjhwwqa55ff6a23ac019695809341_434x651.jpg) Source: [10 Ways to Wear Ankle](https://goo.gl/DKxNvX) 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 ![Coat and Khakis](https://resize.allw.mn/1028x0/filters:format(webp)/filters:quality(70)/content/n6/v5/u89k1d8b55ff6a2491a87137991416_585x878.jpg) Source: [whowhatwera.com](https://goo.gl/ZWGuXv) 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 ![Pencil Skirt and Cardigan](https://resize.allw.mn/1028x0/filters:format(webp)/filters:quality(70)/content/vm/u6/kua2g17v55ff6a24a3cf2021093860_600x900.jpg) Source: [An Ode to Pencil Skirts](http://offbeatandinspired.com/) 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 ![Plaid Scarf and Sweater](https://resize.allw.mn/1028x0/filters:format(webp)/filters:quality(70)/content/cr/kh/r7shvjj255ff6a2480bc1190765025_400x600.jpg) Source: [7 ways to style a](https://goo.gl/GwJo7Q) 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 ![Cuffed Denim and a Flowy Coat](https://resize.allw.mn/1028x0/filters:format(webp)/filters:quality(70)/content/qq/zz/pbh7pv0y55ff6a24c4aac170185107_480x640.jpg) Source: [babble.com](https://goo.gl/Pz1CyE) 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 ![Plaid Dress](https://resize.allw.mn/1028x0/filters:format(webp)/filters:quality(70)/content/tx/uz/w2grsats55ff6a25caf74559884371_585x799.jpg) Source: [Celebrity Style and Fashion Trend](https://www.whowhatwear.com/) Lots of great layers going on and the white booties add an unexpected touch. ## 10. Dark Skinnies and a Coat ![Dark Skinnies and a Coat](https://resize.allw.mn/1028x0/filters:format(webp)/filters:quality(70)/content/b5/hh/sg7rx5g655ff6a26178b7259635608_585x893.jpg) Source: [Celebrity Style and Fashion Trend](https://www.whowhatwear.com/) 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 ![Cuffed Jeans and a Sweater](https://resize.allw.mn/1028x0/filters:format(webp)/filters:quality(70)/content/zr/ie/ncuoc3gj55ff6a25cba1c743459098_550x827.jpg) Source: [10 Ways to Wear Ankle](https://goo.gl/DKxNvX) 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 ![Boyfriend Jeans](https://resize.allw.mn/1028x0/filters:format(webp)/filters:quality(70)/content/cg/c1/vwa6vpat55ff6a261f7fc701625261_550x846.jpg) Source: [The One Staple We'd Wear](https://www.popsugar.com/fashion/Celebrities-Boyfriend-Jeans-32761244?slide=6&image_nid=32761252) Jessica Alba paired her military jacket with distressed boyfriend jeans and heeled ankle boots. ## 13. Cardigan, Coat, and Skinny Jeans ![Cardigan, Coat, and Skinny Jeans](https://resize.allw.mn/1028x0/filters:format(webp)/filters:quality(70)/content/su/a6/x4l2c3wl55ff6a264c487846079252_600x1105.jpg) Source: [Top 10 Ways to Wear](https://www.topinspired.com/top-10-ways-to-wear-leggings/) 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 ![Belted Dress](https://resize.allw.mn/1028x0/filters:format(webp)/filters:quality(70)/content/hx/nc/katrdm5b55ff6a2772cc8758362982_600x848.jpg) Source: [A Clothes Horse: Photographic Memory](http://www.aclotheshorse.co.uk/2010/07/photographic-memory.html?utm_source=feedburner&utm_medium=feed&utm_campaign=Feed:) 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 ![Denim Jacket and Tank Dress](https://resize.allw.mn/1028x0/filters:format(webp)/filters:quality(70)/content/tw/ua/z8uo57rs55ff6a27b707e115344160_433x650.jpg) Source: [Wendy's Lookbook](https://www.wendyslookbook.com/) 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 ![Frayed Denim and Striped Jacket](https://resize.allw.mn/1028x0/filters:format(webp)/filters:quality(70)/content/qx/ys/qpepjvmz55ff6a2809da1643529312_600x900.jpg) Source: [Man Repeller](https://repeller.com/) Mixing stripes with animal print? Yes! Channel your inner street style star by mixing prints with some frayed denim. ## 20. Dark Denim ![Dark Denim](https://resize.allw.mn/1028x0/filters:format(webp)/filters:quality(70)/content/ga/nn/wnzyb76y55ff6a2880057210191255_600x900.jpg) Source: [How to Master Bohemian Style](https://stylecaster.com/bohemian-style-ideas/) 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 ![Long Sweater and Pencil Skirt](https://resize.allw.mn/1028x0/filters:format(webp)/filters:quality(70)/content/qr/t3/uxq305nl55ff6a283379b127660068_585x878.jpg) Source: [How to Wear Ankle Boots](https://www.whowhatwear.com/ankle-boots-for-fall/slide8) 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 ![Floral Dress](https://resize.allw.mn/1028x0/filters:format(webp)/filters:quality(70)/content/f5/vn/d05r3x0x55ff6a2b288dd201375733_600x900.jpg) Source: [Pinterest](https://www.pinterest.com/) 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 ![Flowy Skirt and Long Coat](https://resize.allw.mn/1028x0/filters:format(webp)/filters:quality(70)/content/zz/zy/p4qyrt4o55ff6a2946d5a421000563_585x826.jpg) Source: [Celebrity Style and Fashion Trend](https://www.whowhatwear.com/) 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 ![Blazer and Belts](https://resize.allw.mn/1028x0/filters:format(webp)/filters:quality(70)/content/xt/us/jf5y9skd55ff6a2952d57011602914_585x878.jpg) Source: [Celebrity Style and Fashion Trend](https://www.whowhatwear.com/) I am in love with this gray blazer worn with belted ankle boots. You look like you mean business! ## 25. Slouchy Jacket and Beanie ![Slouchy Jacket and Beanie](https://resize.allw.mn/1028x0/filters:format(webp)/filters:quality(70)/content/ie/mn/hjpx4u1x55ff6a2956d2d080845167_600x899.jpg) Source: [How to Master Bohemian Style](https://stylecaster.com/bohemian-style-ideas/) 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 ![Long Kimono Jacket and Crop Top](https://resize.allw.mn/1028x0/filters:format(webp)/filters:quality(70)/content/ok/is/lpxz16im55ff6a296c8f7512543142_463x1136.jpg) Source: [How to do the Boho](https://glamradar.com/how-to-do-the-boho-chic-look-for-fall-glam-radar/) 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 ![Flared Denim on Denim](https://resize.allw.mn/1028x0/filters:format(webp)/filters:quality(70)/content/r4/nf/z5j180th55ff6a2a38cbb996116309_585x807.jpg) Source: [Celebrity Style and Fashion Trend](https://www.whowhatwear.com/) 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 ![Oversized Coat and Cuffed Pants](https://resize.allw.mn/1028x0/filters:format(webp)/filters:quality(70)/content/lr/er/eiiigd6p55ff6a2a65b46628476045_585x874.jpg) Source: [Celebrity Style and Fashion Trend](https://www.whowhatwear.com/) 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 ![Fitted Denim Top and Skinny Jeans](https://resize.allw.mn/1028x0/filters:format(webp)/filters:quality(70)/content/xs/bh/yltorfzm55ff6a2b1b464173004487_600x900.jpg) Source: [15 Things Stylish Women Do](https://www.popsugar.com/fashion/Habits-Stylish-Women-37115440) 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? 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