6 Foolproof Skirts, Pants and Dresses to Wear With All Your Ankle Boots

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(Image credit: @aimeesong)

In order to make my stories as helpful as possible, I often reach out to my close friends and colleagues to find out what it is they are struggling with fashion-wise. Sometimes, they need help tracking down the perfect pair of jeans at a certain price point, and other times, they want to know about all the latest trends, but this time, I will admit I was a bit surprised by their current conundrum. It seems that figuring out just the right pieces to style their ankle boots with is proving to be rather difficult, so naturally, I started writing a story on it.

Ankle boots are a wardrobe workhorse, so styling them should be a no-brainer, but the more I thought about it, the more I understood the specific points of confusion that could arise, including flattering hemlines, seasonally appropriate pairings, and everything in between. Ahead, I gathered a handful of outfits that break down the easiest ways to style your ankle boots thanks to some of the industry's most stylish influencers. So sit back, relax, and get ready to take note of the foolproof ankle boot outfits you need to re-create ASAP.

Skirts

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(Image credit: @jen_wonders)

The length of your skirt is everything when it comes to ankle boot styling, and it just so happens that miniskirts will work with any ankle boot style time and again. This season, stay on trend and try a tweed skirt suit and tights to make even your most basic of ankle boots feel forward.

Get the look:

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(Image credit: @alyssainthecity)

Midi skirts might be my favorite option to wear with ankle boots. The duo seems to work on a variety of body types and heights, making it a foolproof seasonal outfit to keep on heavy rotation in your closet. Yes, knee-high boots also look incredible with midi skirts, but ankle boots will also do the trick. 

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Pants

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(Image credit: @ada_oguntodu)

There is nothing sleeker than crisp tailored trousers and cool ankle boots. While more traditional pointed-toe block heels might be your first instinct, we are loving the way chunky lace-up boots look with the classic pant style, especially for winter. 

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Get the look:

Dresses

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(Image credit: @misodam)

Mid-length dresses are always going to be your best bet when it comes to ankle boot styling. To ensure you aren't distracting too much from the dress you're wearing, we suggest opting for a simpler boot shape that skims the natural line of your leg and ankle, creating sleek proportions with your frock of choice. 

Get the look:

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(Image credit: @mariabernard)

Even in the cooler months, minidresses can be one of the most useful pieces in your wardrobe. Throw on an oversize blazer, a pair of tights and platform ankle boots, and instantly, even the most summery dress becomes seasonally appropriate. 

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Editorial Director

Lauren Eggertsen is currently the editorial director of Who What Wear and has worked at the company for over eight years, where she started as an associate editor and has since worked her way up. Lauren has over 10 years of experience in the fashion editorial space, starting her career with internships at Marc Jacobs, Marie Claire, and The Zoe Report, where she was later hired as their editorial assistant. Lauren has worked in the Los Angeles and New York Who What Wear offices but currently calls L.A. home. It is here where she leads and manages Who What Wear's fashion team and oversees all day-to-day editorial content and large tentpole moments. This includes all of the runway, trend, and shopping-driven content that ultimately helps to build a strong brand reputation within the industry. Lauren's role also includes helping to set the fashion direction for all original photo shoots and often styles many of the celebrity cover shoots, including big names like Kaia Gerber, Normani, and Kristen Stewart.

She has also attended multiple fashion weeks, including New York, London, Milan, and Paris, where her personal style has been featured on sites such as Vogue, Harpers Bazaar, and Elle. She prides herself on discovering and supporting small brands and on her knack for a good vintage shopping find. When she isn't working, she enjoys researching and dining at reputable restaurants around both her neighborhood and the globe.