Overcome The Intimidation Factor Of Tall Boots

A six-step guide.

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At face value, knee-high and over-the-knee boots are tricky. These calf-hugging shoes don’t just blend in with other elements of your look — they command attention. But, intimidation factor aside, these shoe styles can be surprisingly versatile once you find a pair that works for you. Since they’re hero pieces — the type of wardrobe staple that instantly has the power to transform the humblest tee and jeans into a ‘fit — they can make getting dressed up surprisingly low lift. The key is zeroing in on how to wear tall boots in a way that works for your personal style.

According to Agustina Panzoni, Depop's trend and category manager, the coming of fall marks an uptick in interest around the style. In the month of August last year, the e-commerce company saw an 107% increase in searches for knee-high boots as many women begin to build out their seasonal shopping list. But, while interest in the design ticks up every autumn, right now in particular, there’s been renewed buzz in the trend. Tall boots made appearances on a number of major runways — Bottega Veneta, Isabel Marant, and Chloé all included.

“Knee-high and over-the-knee boots started to develop once again as a trend last year,” says Hollie Harding, buying manager for non-apparel at Browns. “This season, the desire for color-pops, glitz, and super-high-heels continues, however the trend is also migrating into daily wear for an everyday work wardrobe. We’re seeing more subtle suedes and leathers increase in popularity, with knee-high boots being the leader in this category.”

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If you’re ready to start exploring the trend again, consider investing in a take that will seamlessly fit your style. Since there is so much versatility in the market, from wider bucket boots to skin-tight iterations, you can test drive what makes the most sense with your current wardrobe. “It can be tough to shop for [tall] boots online, because you want a pair that hits in the right places — and isn't too wide, but isn't too snug on the calves either,” says Alyssa Coscarelli, founder of Infinite. “Especially being quite petite, you're hunting for one that won't swallow the entire length of your legs! Fit is everything with high boots so definitely try a bunch on until you find the pair that clicks.”

Ahead, find six takes on the trend — from romantic to edgy to trend-driven. Try them on for size, and get ready to put your best foot forward for fall.

If Your Style Is Romantic

While you may not first consider styling a tall knee-high boot with a short hemline, Coscarelli notes that the pairing is a simple styling choice that can help usher in your fall wardrobe. “As we make the transition from summer to fall, [tall boots are] great to incorporate with shorter pieces, like skirts and minidresses, to give them a bit of autumn sensibility,” she says. “There's something about the contrast of a powerful OTK boot with something a bit short and flirty that just works so well.”

If Your Style Is Preppy

For those who may not know where to start when it comes to boots, an easy, preppy outfit will always be a winner. “When in doubt, always keep the styling simple and go for comfort,” advises Panzoni. “The great thing about over-the-knee boots is that they are extremely versatile.” Try styling yours with tight jeans or leggings and top with a trench coat.

If Your Style Is Glam

For dressier occasions, knee-height boots play nicely with sleek silhouettes and lots of texture. Coscarelli suggests “anything slinky” when pulling together an evening outfit. Opt for a heeled boot for a fancier feel; Paris Texas is a favorite label of Harding’s if you’re looking for the “perfect statement boot.”

If Your Style Is Trendy

“Western-style over-the knee boots are growing increasingly popular with the rise of cowboy and cowgirl core,” says Panzoni. It’s a sentiment that Harding echoes, adding, “heritage brands such as Isabel Marant and Chloé were front-runners for the trend on the runway last season.” To pull off this of-the-moment style, the trick is to lean just a little bit into the kitsch. Style them tucked into jeans and pair with a western-inspired jacket or shirt for a look that doesn’t skew too costume-y.

If Your Style Is Edgy

“A real stand-out boot moment came from Courrèges on the runway,” says Harding. For fall the label had both a loose iteration with a sharp heel, and a skin-tight over-the-knee design. Both of which happen to pair well with subversive black pieces for a punky Lara-Croft-off-duty look.

If Your Style Is Quirky

Leave it to Copenhagen-based label Ganni to lead the charge on quirky-cool styling when it comes to higher boots. The brand has offered a lug-sole iteration for a few seasons now that offers a welcome contrast to bright, girly pieces like printed tops and ruffled dresses. Try teaming yours with colorful separates for an unexpected twist.

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