8 Outfits With Booties to Rock for Every Season

Model wearing Dakota boot.

Can you wear ankle boots year-round? You betcha! Booties for women come in a variety of designs, heel heights, and silhouettes, offering endless styling opportunities throughout the winter, spring, summer, and fall.

Fall Outfits With Booties

If you are stuck asking yourself how to wear ankle boots, we’ve gotcha. When dressing for autumn, think simple, cozy, and comfy. Find our favorite fall outfits to wear with ankle booties below.

Skinny Jeans and a Button-Down

Nothing says fall fashion quite like the casual outfit consisting of skinny jeans and a flannel shirt. But if flannel's not your forte, you can go with a solid or otherwise printed button-down. Tuck it into the front of your straight leg jeans, tie the bottom into a knot, or leave it open with a cami or basic tee underneath the casual outfit.

Chelsea boots are great for fall because they can be dressed up with a floral dress or down with a pair of boyfriend jeans, and they are often weather-resistant. We're big fans of lugged outsoles and chunkier heels.

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Leggings and an Oversized Sweater

Leggings and black leather ankle boots are an effortlessly flattering pair. This heeled ankle boot combo is comfortable, undeniably cozy, and perfect for fall.

Other options to pair with leggings could be a flannel, denim jacket, a drapey blouse, sweater dress, a slouchy cable-knit cardigan, or an oversized crew-neck sweatshirt. A pair of weather-resistant combat-style boots or Chelseas will finish the look.

Winter Outfits With Booties

In the winter, you'll want to prioritize staying dry and warm—but that doesn't mean you have to sacrifice style. Check out our best-loved bootie looks for cold weather below.

Black Jeans and a Trench Coat

Like a little black sweater dress, you can always fall back on black straight leg jeans when you feel like you have nothing else to wear. To look put-together while staying plenty warm, slip on a long trench coat and maybe a beanie for good measure. A pair of stacked-heel ankle booties will elevate this look, making it work-ready and going out-approved.

Head-to-Toe Athleisure

Staying warm in the winter is crucial, but your comfort is important too. That's why we love a head-to-toe athleisure look on casual days.

Whether you're partial to yoga pants, half-zip jackets, or coordinating sweatsuits, a pair of sneaker booties are the cherry on top (or bottom) of this cold-weather ensemble—extra points if they're weather-resistant.

Model wearing the Everly boot.


Spring Outfits With Booties

The spring season is a great time to freshen up your wardrobe. However, you don't have to say farewell to your beloved heeled ankle boots. Find our go-to spring outfits with heeled booties below.

Wide-Leg Jeans and a Tee

Wondering how to wear ankle boots with jeans? Wide-leg jeans are laid-back and versatile with an on-trend appeal. With that said, you don't need to go all out with your top—a simple T-shirt is an excellent choice.

We recommend a fitted tee or a short-sleeve crop top. As for your shoes, low ankle booties offer an air of sophistication while aligning with the spring weather.

Flowy Skirt and a Fitted Shirt

We also love the look of a flowy midi skirt for spring—asymmetrical and pleated midi skirts work well too. To balance out the fullness of your midi skirt, opt for a fitted shirt, such as a bodysuit or a plain stretchy t-shirt.

With spring in full bloom, wedges are a wardrobe staple—but your options don't end at sandals and espadrilles. Stacked-heel wedge booties are a practical, elegant choice.

Summer Outfits With Booties

If you think you have to phase out your heeled booties come summer, think again. Check out these warm-weather ensembles to wear with booties.

White Jeans and Nautical Stripes

White jeans and nautical stripes are a classic combo—and the stripes don't have to be on your shirt either. Consider white wide-leg jeans with a navy tee and a gauzy striped neck scarf. Finish the look with low leather ankle boots in taupe, brown, or camel.

Maxi Dress and Wedge Booties

Flattering on all figures and exceedingly comfy, maxi dresses are a go-to in the summertime. Aside from footwear, you don't need much else for this one-and-done outfit. We recommend suede wedge booties with cutout detailing on the sides, or try a chunky heeled closed toe sandal for a similar look with added breathability.

Seasonless Ankle Boots from TOMS

Inspired by these looks? TOMS carries a wide selection of women's footwear that can be worn year after year, season after season. Shop our women’s boots and booties today!

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Reviewed By Kendall Pilgrim 

Kendall Pilgrim is an LA-based writer and editor determined to go all the places and see all the things. She’s been operating in the footwear space for 3 years, writing about the latest trends or styles and helping brands make bold statements through innovative copy.