21 Outfits That Prove Ankle Boots Are a Year-Round Trend

Plus, the best ones to shop.

Summer’s in the air and chances are, because of it, you’re planning to trade in your thick, knit sweaters and boots for sundresses and summer sandals. However, before you put away all of your fall and winter shoes, hold on to your ankle boots. These low-rise booties are versatile shoes that you can wear all year—the key is all about how you style them, and there are so many ways to do so.

From pairing them with dresses for a day date or leather bottoms for a fun night out, you can truly make ankle boots work for any occasion, aesthetic, and season. If you don’t believe us, keep scrolling to get ideas on how to wear ankle boots.

1. How to wear ankle boots with skinny jeans:

how to wear ankle boots

Pairing ankle boots with skinny jeans is a classic look that compliments everyone—no matter what Gen Z might think. You can dress them up by wearing them with a blazer or keep it casual with a graphic tee.

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The Regan Boot

$$178.00
Shop it Madewell

2. How to wear ankle boots with mom jeans:

how to wear ankle boots

Loose-fitted mom jeans are having a major moment right now and luckily, you can pair the trend with ankle boots for a laidback look. We recommend going with a pair of boots that have a form-fitting shaft so that it neatly tucks under the loose jeans.

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Steve Madden Betty White Ankle Boots

$99.95
Shop it Steve Madden

3. How to wear ankle boots with flare jeans:

how to wear ankle boots

For the ultimate ’70s-inspired look, style your boots with flare jeans. Since the bottom cut of these jeans are so loose, you can wear them with any kind of ankle boot.

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Vince Camuto Genedy Western Bootie

$69.99
Shop it DSW

4. How to wear ankle boots with straight-leg jeans:

how to wear ankle boots

If you prefer straight-leg jeans, rest assured you can wear your ankle boots under them. We recommend going with a pointed toe, which looks great underneath the cut.

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Marc Fisher Eilise Bootie

$94.99
Shop it DSW

5. How to wear ankle boots with a midi dress:

how to wear ankle boots

Wearing a midi dress with your ankle boots will earn you some style points in our book. This dress length allows your shoes to peek through so they can get the attention they deserve.

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Marc Fisher LTD Jarli Pointy Ankle Boots

$$189.00
Shop it Marc Fisher

6. How to wear cowgirl ankle boots:

how to wear ankle boots

Night gown-inspired dresses are comfortable and lightweight, making them great for the warmer months. Pair your dainty slip-on with an ankle cowgirl boot, which is a fun way to showcase contrasting styles that work great together.

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Roy Western Bootie

$59.99
Shop it DSW

7. How to wear ankle boots with a maxi dress:

how to wear ankle boots

A maxi, floral dress with ankle boots is the free-spirited outfit of our bohemian dreams. The best part is you can comfortably wear it during those cooler summer nights and into the fall. 

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Lucky Brand Basel Boots

$129.00
Shop it Zappos

8. How to wear ankle boots with a T-shirt dress:

how to wear ankle boots

T-shirt dresses make getting dressed so easy and mindless. From running errands to meeting up with friends, you can’t go wrong with a chunky pair of Doc Martens ankle boots, which give it such a cool girl vibe.

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Doc Martens 101 Yellow Stitch Smooth Leather Ankle Boots

$140.00
Shop it Dr Martens

9. How to wear combat ankle boots:

how to wear ankle boots

Something about this balance of femininity from the short, flowy dress and utilitarianism from the structured, combat boot just works. It’s modern, fashionable, and, if you ask us, gives you the perfect excuse to go out on the town to show off your look.

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Steve Madden Latch Bootie

$99.99
Shop it DSW

10. How to wear ankle boots with leggings:

how to wear ankle boots

Leggings aren’t only reserved for dates with your couch and Netflix. You can dress them up to look more elevated while running errands or going for a coffee date. Opt for a monochromatic outfit, including a neutral colored pair of ankle boots.

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Steve Madden Howler Sand Suede Ankle Boots

$99.95
Shop it Steve Madden

11. How to wear ankle boots with patent leather leggings:

how to wear ankle boots

Patent leather leggings are proof you don’t have to sacrifice comfort for style, especially when you throw on a comfy sweater on top or a loose-fitted T-shirt. 

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Donald Pliner Devasp Leather & Suede Studded Booties

$298.00
Shop it Nordstrom Rack

12. How to wear ankle boots with sweatpants:

how to wear ankle boots

If you prioritize comfort over everything else, we’re excited to report that yes, you can wear ankle boots with sweats. Make it look a little more put together by opting for a neutral color and slim fit so that you can neatly tuck the pants into your boots for a comfy and stylish look.

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Erin Booties

$89.95
Shop it Nordstrom

13. How to wear ankle boots with work pants:

how to wear ankle boots

Linen trousers are work friendly pants that can also be worn on the weekends because of their relaxed fit. Pair them with a rounded toe ankle bootie and any blouse of your choosing.

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Mango Leather Heeled Boots

$100.00
Shop it ASOS

14. How to wear ankle boots with high-waisted trousers:

how to wear ankle boots

What’s corporate attire without a blazer? Make it feel a little more fashion-forward by choosing an outfit with a neutral color palette and pairing high-waisted trousers with ankle sock booties.

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Steve Madden Maxwell Blush Ankle Boots

$139.95
Shop it Steve Madden

15. How to wear ankle boots with a midi skirt:

how to wear ankle boots

Silk, mid-length skirts are versatile and work appropriate when spruced up with the right ankle boot and top. If your work environment is more chill, a crew neck T-shirt is a great option.

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Sam Edelman Regaen Ankle Booties

$160.00
Shop it Sam Edelman

16. How to wear ankle boots with a short flowing skirt:

how to wear ankle boots

Chunky knit sweaters, short skirts, and booties are a casual and easy way to get good use out of your shoes for multiple seasons.

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Public Desire Cameo Contrast Panel Boots

$56.00
Shop it ASOS

17. How to wear ankle boots with a mini skirt:

how to wear ankle boots

Show off your legs with a fitted mini skirt, leather ankle boots, and a cropped graphic sweater. It’s a perfect look if your aesthetic is a mix between sporty and edgy.

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The Brava Black Ankle Boots

$435.00
Shop it Bells and Becks

18. How to wear white ankle boots:

how to wear ankle boots

White boots are one of those items you need in your capsule wardrobe. They won’t go out of style and can be paired in multiple ways, including a flowing skirt that will show them off in all of their glory.

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Tessa Vagabond Shoemakers

$175.00
Shop it Zappos

19. How to wear ankle boots with shorts: 

how to wear ankle boots

We’re very big fans of matching tops and bottoms that make you feel put together with very little effort. Pair your sweat shorts with ankle boots for a casual and comfy fit.

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Low Heel Laced Fabric Ankle Boots

$69.90
Shop it Zara

20. How to wear lace-up ankle boots:

how to wear ankle boots

The right pair of ankle boots can transform any outfit. Case in point? Laced-up ankle booties. It takes a simple outfit, such as jean shorts and a button-up, and instantly turns it into a stylish ensemble for a night out.

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ASOS Ricky Pointed Toe Lace Up Boots

$64.00
Shop it ASOS

21. How to wear mesh ankle boots:

how to wear ankle boots

If you have a pair of statement boots that deserve to be in the limelight, like these mesh ones, pair them with shorts so everyone can admire your incredible fashion sense.

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Wide Heel Mesh Ankle Boots

$89.90
Shop it Zara