Out of Fall 2023’s Biggest Fashion Trends, This Is the One I Can’t Stop Wearing

Eva Thomas

Thu, November 2, 2023 at 2:00 AM UTC

4 min read

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Once you try tall black boots, you’ll never go back.

While it’s hard to pick my favorite season — because I’m indecisive and because I love them all, okay! — if I had to pick just one, I would say fall. I grew up in Minnesota, and while autumn always meant that the brutal winter was coming (brrr!), it was also among the most beautiful times of year, with leaves changing colors from green to mixes of red, yellow, and orange. Lightweight summer clothes were replaced with cozy, cuddly sweaters, and sandals (which TBH, I never really like wearing anyways) were packed away in lieu of more practical shoes, like boots, which are easily my favorite seasonal staple. Minnesota winters obviously call for durable, shearling-lined styles, because it can get as cold as minus 32 degrees Fahrenheit, but I always had a thing for the more, well, trendy options, which I could only really wear when I moved to New York. Milder weather equals more freedom with fashion, duh!

That said, I’ve worn plenty of boot styles over my time working in fashion in the Big Apple. I’ve worn Uggs (which will always have a place in my heart); I’ve trudged around in chunky combat boots, some of which weigh more than my sister’s cat; I’ve slipped into cowboy boots, which sure, I like a lot, but they aren’t the easiest to style if you’re lacking sartorial creativity. But out of all the ones I’ve tried, I’ve reached for my trusty black knee-high boots more than any other, and considering the sheer number of boots I have, that’s saying a lot.

Tall black boots are having a major resurgence in fall 2023 — but just because they’re in the midst of a comeback doesn’t mean they ever really went away. The boot style is perhaps the most timeless of all, and when you think back on fashion history, the trusty footwear was always there. Some of Carolyn Bessette-Kennedy’s most memorable looks included tall black boots, and Julia Roberts’ iconic Pretty Woman character rocked them like it was nobody's business. To this day, it’s those ensembles minimalists strive to recreate, with the footwear being the grounding component

Steve Madden Lavan Pointed-Toe Knee-High Boot

$170

Open Edit Erik Wedge Tall Boot

$130

The tall black boot can be whatever you want it to be; it can be classy, it can be sassy, and it can be a little daring, and that’s exactly why I’ve been wearing it nonstop. But even though it’s so multi-faceted, it’s inherently timeless, which is why it’s so appealing.

Just take it from celebrity stylist Neil J. Rodgers, the designer behind his eponymous shoe label that crafts boots out of the finest Italian leather. “Tall black boots are a modern classic. Chic, versatile and timeless, they're as essential to fall dressing as sandals are to summer,” he tells InStyle over email. He adds that a good pair of tall black boots is a key wardrobe investment, suggesting, “choose quality and style over a trending detail such as a heavy metal work or embellishment.”

I hard second that statement — the tall black boots I wear the most often are the ones with the least bells and whistles. I love my Inez Paloma Boots because of the timeless silhouette and sleek, buttery-soft leather upper; they pair well with everything, from skirts to dresses to jeans, and that’s exactly what makes them worth the $495 price tag. Versatility is at the heart of a really good investment piece, and nothing is more versatile in the shoe world than black knee-highs.

Ready to see what tall black boots are all about? Shop some go-to styles below, and yes, you already know I’ll be adding a new pair to my rotation as well.