How to Wear Your Ankle Boots Like a Celebrity

Ways to Style Ankle Booties

If there is one staple your closet needs, it’s the versatile ankle boots. Perfect to wear with dresses, skirts, and jeans, the right ankle boots can make you look incredible and feel comfy, both at the same time.

From exploring the great outdoors to going to an event, I have got the right ankle boot styles to help you pull your look together.

Ankle boots and skirt

Ankle boots are a great way to update a classic skirt outfit. There are many ways to wear ankle boots with skirts, no matter the length. Whether you’re rocking a short skirt on the weekend or a maxi skirt to work, there is an ankle boot that will work with your outfit. Midi or knee-length skirts might be my favorite option to wear with ankle boots, that is because it seems to always work, no matter the shape of your body and height.

If you’re ready to swap in separates for a dress, try your ankle boots with a skirt. You can wear a pair of stiletto ankle boots with a knee-length skirt and a polished button-up shirt. Then add to it a blazer on top or a knitted cardigan. Take a look at these two outfits here.

Keira Knightley at the press conference in Toronto, wearing black ankle boots with a green skirt, white elegant top, and a black blazer. Love the soft smoky eyeshadow makeup that always makes her look stunning.

Larsen Thompson wearing black leather ankle boots, a plaid skirt, a leopard top, and a black knitted cardigan, before a fashion show during Milan Fashion Week

Ankle boots and a short dress

Another trendy way to wear ankle boots is with a dress. You can choose a mini dress, long dress, bohemian style dress or even an elegant dress – they all will look great!

Here are 7 tips to remember when wearing ankle boots with a dress:

Balance top and bottom.
Nude booties elongate the legs.
Cowboy boots make the look casual.
Ankle booties flatter a midi/knee-length dress.
Pointy toe booties are elegant.
stiletto ankle booties are sexy.
Wide cuff booties slim legs.

With this in mind, let’s take a look at these chic dresses and the versatile dark boots that make for great style combinations.

Take a look at Cameron Diaz’s outfit where she is wearing the ankle booties with a blue sexy satin dress on her way out and about for Celebrity Candids, East Village hotel, New York.

Tyra Banks (wearing a Prada dress and black ankle boots) at arrivals for Conde Nast 4th Annual FASHION ROCKS Concert, Radio City Music Hall at Rockefeller Center, New York.

Alexa Chung at arrivals for The Charlotte Ronson and JCPenney’s celebration of I Heart Ronson, The Lighthouse at Chelsea Piers, New York – wearing a short red dress with long sleeves, silver statement necklace, black leather purse bag, rivet bracelet, and black stylish ankle booties. The perfect outfit for going out or for the weekend.

And here is Alexa Chung wearing a vintage dress and carrying a Louis Vuitton bag at arrivals for THE SEPTEMBER ISSUE Premiere, MoMA Museum of Modern Art, New York. In love with this dress!

Ankle boots and jeans

The classic way to wear ankle boots is in jeans. Generally, boots with a taller shaft look best with skinny jeans tucked in, and boots with a lower shaft look better with jeans untucked or cuffed. Take a look at this photograph where pretty Jessica Alba is wearing ankle boots and skinny jeans.

Jessica Alba wearing nude suede ankle boots, skinny jeans, a leather bag, a white top, and a long knitted cardigan, at the TOMS for Target Holiday Partnership celebration, The Bookbindery, Culver City. A stylish casual outfit that can be great to wear also for work.

Ankle boots with legging

Ankle boots can look really chic with leggings, especially black leggings or faux leather leggings. Here is a casual outdoor outfit with black leggings, a blue plaid buttoned shirt, and a stylish mid-length winter coat.

Blake Lively at talk show appearance for The Late Show with David Letterman – TUE, Ed Sullivan Theater, New York

Ankle boots and sportswear

2020’s pandemic made people being stuck in their homes for weeks, which made many people respond by stocking up hoodies, yoga pants, sweatshirts, and other sportswear. Take a look at this blogger’s outfit that best describes 2020-2021’s popular trend, which is actually comfy and quite cool.

To get this effortless look, like you randomly threw a few things on, and just happened to look put-together, you can wear a monochromatic sport suit, ankle boots, and a topcoat or a blazer. Adding dark sunglasses can boost your total chic look!

Ankle boots and suit

Ankle boots look just as great with women’s suits as they go with denim, so step outside your comfort zone and give the style a whirl. Here are a few inspiring outfits for women – street style appearance during Milan Fashion Week.