A tall boot can often prove difficult when it comes to getting dressed. While some might be scarred from the riding boot and skinny jean styling madness of the 2010s, others are embracing the tucked pant and riding boot revival. Beyond this, tall boots are a versatile wardrobe staple and we’re here to prove that. With so many runways offering inspiration and our favorite it-girls also embracing the trend, we’ve been thinking a lot about tall boots through a modern lens.
Naturally, we turned to a few industry insiders to gauge ideas for how to style ours. Perhaps that entails pairing a white boot beneath a ruched slip dress or tucking straight-leg denim into a heeled black pair. Perhaps it involves throwing on a leather jacket or pairing with extra long shorts. Truly, the options are endless. Are you intrigued yet? Continue scrolling to offer foolproof advice for how to style tall boots with six outfit formulas to get you started.
Slip Dress + Leather Jacket
CENTER COURTESY OF INSTAGRAM/@MECCAJW
Just when you thought this would be an all-black ensemble, stylist Mecca James-Williams switches it up with a pair of white leather boots. She embraces the leather trench coat trend and adds some statement journey for a little pizazz. Then, a statement handbag accentuates everything.
Blazer + Statement Tights + Mini Skirt
CENTER COURTESY OF INSTAGRAM/@GOODWOODX
If the last look was minimal, this one is anything but. Layer on all of your classic staples, then throw everyone off with a pair of crazy statement tights. Suggestion: animal print will always be in style and will always be a foolproof way of adding edge to a look. A slightly chunk boot is the key finishing touch.
Tank + Jeans
Taking a note from Angelica Huston's style book, Diana Bartlett opted for a simple tank and jeans to pair with her heeled boots. The key here is to make sure the leg of the denim isn't too narrow in order to stay modern. Consider adding accessories to take this look from minimal to elevated.
Denim Skirt + Peacoat + Fishnet Tights
Courtesy of Tory Burch
At first glance, this Tory Burch look might seem quite simple, but the magic lies in the details. Beyond the navy-coat-and-denim-skirt combo, you’ll notice fishnets peek out at the knees, and shirt cuffs stick out from beneath the coat’s sleeves. This look is the perfect balance of nostalgic, with '90s and early 2000's elements, and modern. Add a croc bag and a pair of aviators, and you’re ready to go.
Aviator Jacket + Button Down + Long Tailored Shorts
Courtesy of Lemaire
Lemaire stole my heart with their whole Fall ‘23 collection, but this look, in particular, has held a residence in my mind ever since. I love the slinky boots with the wide-leg Bermuda shorts, the aviator jacket with the crisp shirting. With mismatched long and cropped silhouettes, the tall boots balance the look perfectly. You truly can’t go wrong.
Pinstripe Blazer + Floral Skirt
Courtesy of Dries Van Noten
I pretty much love everything Dries Van Noten does, and this look proves no different. The boxy pinstripe blazer perfectly offsets the floral skirt, which uniquely contrasts the sleek platform boots. Add some perfectly wonky modern jewelry to complete the ensemble. This look is evidence that playing with fashion is always a good idea—sometimes the least expected combinations make the best outfits.
