The 13 Best Stiletto Boots to Dress Up Any Outfit

woman wearing a blazer and stiletto boots

(Image credit: Getty)

published 15 January 2024

I have a boots collection that rivals that of most department stores. I tend to buy a new pair every year before wearing them on repeat for months. And while I love my classic flat Chelsea boots for everyday wear, I have my sights set on finding the perfect pair of stiletto boots. And yes, I do intend on wearing them on nights out with friends or on date nights, because this year is all about getting back into the swing of things when it comes to actually getting dressed again.

My love for stiletto boots wasn't born from a love of walking in high heels, though, which is why I tend to prefer options that have a moderate (or even kitten) style heel height. Comfort is key, even when I'm talking about shoes that come with the skinniest heel in existence. I'm also partial to a knee- or thigh-high boot with a spring-ready midi dress on tricky transitional weather days. And if you do love a very high heel—props to you and your ankles—boots often provide a touch more support, are easier to walk in, and are often way more comfortable than your usual strappy sandal or classic pump would be, which means that you wear them for hours without feeling any pain.

If, like me, you love a good boot and are looking to add a sexier silhouette into your rotation this season, keep scrolling. This list has it all, from thigh-high stiletto boot picks that come in a shiny patent leather to other more simple picks that could totally work for a trip into the office.

Stuart Weitzman Stuart 75 Stretch Bootie

Nothing beats a classic black sock-style bootie. The heel on this pick is also the perfect mid-height for everyday wear, or just for those date nights when you want to amp up your usual jeans-and-a-nice-top outfit.

Mango Squared Toe Leather Ankle Boots

This butter yellow ankle boot from Mango is great for pairing with your winter dresses to make them feel a touch more spring-ready.

SCHUTZ Magalli Knee High Boot

White boots are as spring and summer wardrobe staple. This pair from Schutz works with a dress or overtop of a pair of jeans.

Aeyde Sofie Brandy Nappa Boot

If you need a new work bootie, consider this pair from fashion-insider-approved brand Aeyde.

Jeffrey Cambell Skelter Boot

Jeffrey Cambell knows how to make statement, even when that statement comes in the form of an otherwise classic stiletto knee-high boot!

Larroude Kate Boot

Larroude's Kate Boot has been spotted on celebrities like Vanessa Hudgens, Rita Ora, Mary J. Blige, so it's safe to say that they're worth the investment in this rich chocolate hue.

Reformation Otis Stretch Knee Boot

This low-heeled boot from Reformation offers a slightly chunkier alternative to the classic stiletto boot. Plus, the over-the-knee silhouette is seriously sexy.

Malone Souliers Avis 70mm Boot

Keep these all-white boots clean and they'll become a wear-everywhere staple in your shoe wardrobe. You can't beat the classics!

Steve Madden Viktory Over the Knee Boot

This sky-high heel from affordable favorite Steve Madden has it all. A shiny patent-leather finish, a sleek silhouette, and a perfectly pointed toe. This pair is perfect for when you really want to make a statement.

Wandler Marine Leather Ankle Boots

If you already have a suede bootie in your collection and are looking for something that comes in a leather fabrication, this pair is for you.

Chinese Laundry Elisha Chain Stiletto Bootie

Add some spunk to your boot collection by opting for a pair that features a chain detail, like this one from Chinese Laundry does.

Coach Wynie Bootie

Ruching is trending right now—even on your shoes—which is something that Coach knows all too well.

L'AGENCE Mila Bootie

Think of these booties from L'AGENCE as your favorite sexy lingerie, but for your feet!

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Julia Marzovilla is the Fashion E-Commerce Editor at Marie Claire, where she reviews the latest launches from fashion and beauty brands, finds the best on-sale items around the internet, and interviews experts to find the best products in any category to share with her readers. She also creates shopping guides that span every vertical on the site as an expert in everything from the best laptop bags to the best laser hair removal devices.

In her near decade of experience, Julia has both written for several top outlets in the E-Commerce space and worked at major fashion labels. Prior to joining the Marie Claire team, she contributed similar shopping stories to sites such as Bustle, InStyle, The Zoe Report, Who What Wear, and worked as the Trending Fashion and News Writer STYLECASTER. You can find her across the internet at @JuliaMarzovilla. In real life, you can find her creating shopping guides for her friends, cooking or baking in her too-small kitchen, or buying tickets for the next time Harry Styles is in town.

Julia has a Bachelor’s degree in English with a minor in Journalism from Loyola Marymount University in Los Angeles, California. She lives in New York City, her hometown.