How to Wear Ankle Boots for Women

When you buy a pair of ankle boots, you need a plan for some outfit combos you can make. How to wear ankle boots for women is a broad topic. There are plenty of ways to style everything, from black booties to lace-up rounded toe boot styles. You can build anything from a comfy, casual look to a business-worthy outfit idea. Here are our style tips for creating the ankle boot outfit of your dreams.

A pair of Women's Dalston Vibe 6-Inch Boots in dark brown leather.

How to wear ankle boots with jeans

From your day-to-day looks to a casual night out on the town with friends, there are tons of ways to wear ankle booties with jeans. We'll get to how to wear ankle boots with skinny jeans later, but here's how to pair ankle boots with a variety of wide-leg styles.


How to wear ankle boots with straight-leg jeans

Straight-leg jeans pair the best with tight-ankle booties that can easily sit under the pant leg without causing bulging. Throw on some Women's Dalston Vibe 6-Inch Boots with your straight-leg jeans, and add a white t-shirt and a leather jacket for a cool look that's perfect for going out.


...with boyfriend jeans

​Roll up the cuffs to show off your booties to create a trendy look with some high-waisted boyfriend jeans. Our classic wheat and black Women's Kinsley 6-Inch Waterproof Boots are great for creating a casual look that you can wear to run errands, grab coffee with a friend, or relax on a Saturday. Top off your outfit with a graphic tee and an oversized flannel to complete the lowkey look.

A close-up of an iconic women's Timberland wheat and black boot paired with cropped black skinny jeans.


...with bootcut jeans

Bootcut jeans are made to sit over your boots, so stick to the tighter-ankle styles. They're perfect for casual looks, so a flat ankle boot like our all-black Women's Kinsley 6-Inch Waterproof Boots are perfect for everyday wear. Pair them with anything from a French-tucked button-down to a basic t-shirt.


...with cropped jeans

Cropped jeans are the best when you want to know how to wear short boots with jeans. Show off low-profile boots like our Women's Sutherlin Bay Low Chelsea Boots with skinny and wide-leg cropped pants. Or go high-fashion with Women's Lana Point Buckle Boots, black jeans, and a fashion trench coat.


How to wear ankle boots with dresses and skirts

When it comes down to how to wear boots with dresses, the most important part of your style is going to be confidence. You can pair ankle booties with nearly any skirt; just remember that you're rocking the look, and walk with confidence! Flat ankle boots like our Women's Courmayeur Valley Chelsea Boots pair great with a midi skirt and let you move easily. With a maxi skirt, a block heel boot gives you lift to keep your hemlines from dragging. Try the Women's Lana Point Chunky-Heel Boots with a mini skirt to accentuate your legs. Brown boots pair better with summer and spring fashions, while you can turn towards black ankle boots for fall and winter boots.


How to wear ankle boots with dress pants

Ankle boots are the perfect wardrobe essentials because they're versatile enough to go with nearly any look. Throw on some black leather pointed-toe booties under your slacks and pair it with a blazer for an instant professional look. Going more business casual? Some wide-leg cropped pants paired with a blouse matches with our Women's Sienna High Ankle Boots for a smart take on how to wear ankle boots with pants.


How to wear ankle boots to work

Wearing ankle boots to work but not reaching for your slacks? Luckily, black ankle boots go with just about anything. You can pair suede booties with a professional business dress for a powerful look. Add a heeled boot under your pencil skirt and blouse for a business look that boosts your confidence. With a block heel and no stilettos in sight, you don't have to worry about an unsteady stride.


How to tuck jeans into ankle boots

Circling back to jeans, there's one more fashionable way to style your boots. Read for some wide-mouth ankle booties and tuck skinny jeans into the mouth. The narrower ankle on the jeans helps avoid bunching, and this combo stars on many lists of fall fashion trends, especially when paired with a t-shirt and a chunky cardigan. This tucking technique also applies to how to wear ankle boots with leggings and how to wear tights with dresses and boots, so experiment to your heart's content.


Don't be afraid to mix and match your outfits until you find the look that works for you. Be bold and experiment! And make sure to join our email list or sign up for SMS updates to get all the latest news.