The Timeless Boot Trend I’ll Never Quit

I’m never one to knock a good trend — I give the season’s current cut-outs, chunky loafers, and slouchy suits an emphatic yes. But it’s the classics for me, in the clothes and shoe department a lot of the time, which brings me to one of my favorites: styling my outfits with tall boots. Yes, über hefty boots are in, and another drift I don’t at all oppose. But when I’m craving a more timeless look, it’s all about knee-grazing silhouettes, which are irrefutable wardrobe heroes in smooth leather or suede. Theresa Ebagua, the founder of Chelsea Paris, tells me, “Heeled or flat, tall boots are an essential in every wardrobe due to their versatility. Depending on your mood, you’ll always find a way to style them, either slouched down with jeans, a simple T-shirt, and an oversized blazer for an understated cool look, or with an amazing strappy silk dress for a night out.”

If basics aren’t your usual MO, realize this: just because something’s timeless doesn’t mean it can’t look fresh. Take the ’90s and ‘00s-style minis skirts and bodycon dresses that have made a strong comeback, for example — they’re remarkably well-balanced with a knee-high boot in the mix. “I love the contrast of tall boots with shorter hems in early fall,” says Hannah Spinelli, founder and creative director of the footwear brand Inez. “Of course, they hold their own through the season next to chunky knits and heavier fabrics.” Great for those fine knit polos and oversize sweaters you’ve been stockpiling until sweater weather properly hits — both are quintessentially autumn with tall boots, whether styled with floaty skirts or a slim pair of jeans.

Similarly, knee-high boots are flawless with au courant ribbed midi or maxi dresses or a top-and-skirt set, ideally with a slit to reveal a beautifully designed shaft or a unique detail in all cases. But, to me, there’s no better formula than a tall boot with a midi dress. The combination looks polished as ever and “elongates your silhouette,” as Marina Larroudé, founder of her namesake line, Larroudé, explains. Plus, they work with dress silhouettes of all kinds — A-line, tiered, fitted, flared, asymmetric, and beyond.

No matter how you wear tall boots, Spinelli notes, “tall boots are statement pieces that both ground and elevate an outfit. Like a blazer or a piece of jewelry, a high shaft in supple calf or embossed leather brings a high-end attitude to any look.” Ready to get your tall boot outfits in order? Keep scrolling to discover five chic formulas you’ll love rotating through this fall.

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Peeking From A Midi Skirt

Tall boots and a midi skirt read classic and feminine — one of my and Spinelli’s go-to looks. “[I love] our mocha croco Paloma peeking out from under a full midi skirt, paired with a fitted top to balance the proportions.” A pleated skirt always feels modern and fresh, not to mention a must-have this season. For more of a Y2K vibe, opt for a lower-slung skirt or a design with ties or cut-outs.

With A Long Dress

“I tend to wear long dresses all the time, and I love to pair them with a tall boot,” says Larroudé. Same. My favorite combination is a printed midi with a boot in a color that picks up accents from the motif. To finish, I frequently go for a sleek bag and polished gold jewelry (usually piled on).

Try A Print

“Boots allow one to bring a personal twist, either with a soft sexy classic Nappa leather, or a statement print like our Vann Zebra black and white boot, or the Queen boot in camel zebra print,” Ebagua says, both of which are soon to be available. “It’s that ‘je ne sais quoi’ that elevates the look, showcasing your confidence and individuality as you turn heads.”

Make It A Mini

“When I’m [going] for a sexier look, I wear tall boots over jeans or with a mini skirt,” Larroudé tells me. When taking the leg-baring route, lean into nostalgia á la Cher Horowitz by pairing knee-high boots with a chocolate leather brown skirt, plaid top, and small bag.

Layered Over Jeans

More of a jeans gal? You can’t go wrong tucking a slim-fitting pair into tall boots with a button-down shirt or sweater to top it all off. Again, balance is the key to mastering this combo — aim for an oversize fit on top to avoid tight, head to toe. To liven up this casual combo with versatile black boots at the crux, try combining graphic prints together in black and white.