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

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.


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:

Mango Tweed Miniskirt (£36)

H&M+ Jersey Top (£10)

By Far Este Leather Ankle Boots (£410)

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.

Get the look:

& Other Stories Relaxed Mock Neck Sweater (£75)

Ganni Ruffled Printed Stretch-Mesh Wrap Skirt (£180)

Topshop Maile Black Point Boots (£59)


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.

Get the look:

ASOS Curve Oversize Dad Suit (£98)

Nobody Denim Luxe Rib Long Sleeve (£124)

Off-White Hiking Boots (£712)

Jeans can sometimes be the trickiest item to pair with your ankle boots due to varying hems and shaft heights. To ensure your pants always hit your ankle boots just right, opt for a longer pair of jeans that will cover most of the boot, leaving out just the tip of the toe. Trust me.

Get the look:

Pixie Market Leather Sleeve Tie Jacket (£150)

Goldsign High-Rise Wide-leg Jeans (£360)

Miista Zelie Lace Up Booties (£283)


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:

H&M Fine-Knit Turtleneck Jumper (£18)

Zara Asymmetric Poplin Dress (£30)

Reike Nen Patent 60mm Ankle Boots (£445)

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.

Get the look:

H&M Double-Breasted Belted Hacket ($40)

Jacquemus Murano Floral-Print Cotton and Linen-Blend Mini Dress (£715)

Simon Miller High Raid Boots (£520)

Next up, shop the designer items that are about to go viral in 2020.

This article originally appeared on Who What Wear

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