How to Wear Ankle Boots, According to a Stylist
Now that the weather is getting cooler and fall is just around the corner, it’s time for all of us to put down our sandals and unpack our very best boots. Boots are my personal favorite type of shoe and when it comes to the most versatile style for everyday life and the transition to autumn, I always go for ankle boots. I’m not alone: Fashion stylist Sarah Nearis also loves good ankle boots, calling them her “personal favourites” and defining the style as one that “covers the entire foot and reaches to or just above the ankle”.
Nearis also says that ankle boots are one of the easiest types of boots to wear and that there are endless fashion options to mix and match them. “Ankle boots are so versatile depending on style and design,” she says, adding, “there are so many ways to style them.”
If you need more outfit inspiration, read on for our stylist-recommended tips and tricks for taking your ankle boot ensembles to the next level.
With trousers
For an elegant look, Nearis recommends styling your ankle boots with a pair of quality trousers. “I love pairing pointy heeled boots with a great pair of trousers or a suit,” she says. I love this look too and find the short height of the ankle boots lend themselves to being worn with tailored pants.
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Farm Rio Spotted Macaw Organic Cotton Bodysuit
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Athleta Nolita Wide Leg Pants
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Open wide leg edit suit pants
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Alfani Step N’ Flex Women’s Jacklynne Pointed Toe Booties
With a suit
As Nearis said, ankle boots look fabulous with pants or with a suit. Finally, if you’re committed to this Abbey Road-inspired look, why not go all the way? Nearis recommends a pointed-toe boot, but is also happy to opt for a “classic heel” to give you more height and add a feminine touch to a potentially androgynous look.
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Ann Taylor The notched blazer with two button cross tie
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Ann Taylor – The slim fitting, high waist, ankle length cross fabric pant
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Victoria Beckham woven blazer
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Victoria Beckham woven straight leg pants
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Sam Edelman Wrenley bootie heel
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Kelly & Katie Aveya Booties
With a slip dress
A slip is one of the ultimate fall essentials, no matter the season. Its simplicity allows it to be combined with a range of accessories and shoe styles, including the ankle boot. Nearis says she especially loves pairing her western boots with slip dresses. Personally, I’m a fan of the lace-up ankle boot and like to embellish the slip dress with a touch of yellow gold jewelry.
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Intimissimi silk midi briefs
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Bebe Solid satin bias dress
Isa Noy Coco Lover hand chain
Child of Wild Star Dust CZ Necklace
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Isabel Marant Dewina western boots
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dr Martens 1460 Boots – Ladies
With leather
Many ankle boots are already made out of leather, but Nearis says you should consider adding leather elements or accessories to make your boots stand out or elevate an otherwise ultra-feminine outfit. For example, she says she loves to throw a leather jacket over her slip when she wears it with boots. You can also combine the boots with leather trousers, jewelery or hair accessories – the possibilities are endless.
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Levi’s Dad women’s faux leather bomber jacket
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Gap High Rise Faux Leather Vintage Slim Pants
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We are Chimmi vegan leather hair tie
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Tory Burch Roxanne woven chain bracelet
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Toms Women’s Everly Cutout Block Heel Booties
Thursday Boots Downtown Bootie for women
Meet the expert
Sarah Nearis is a fashion stylist and creative director. She lives in Los Angeles and Nashville.