16 Pointed-Toe Boots To Make The Sidewalk Your Catwalk

Photo: Courtesy of Irina Grechko.
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Sorry, but it might be time to boot all your shoes to the curb. Pointed-toe boots are in, and they are all we want to wear this season. From knee-high to ankle boots, the timeless shoe is a wardrobe staple for its ability to elevate any look, taking it from relaxed 'fit to NYFW-ready.
Find the best pointed-toe boots ahead, whether it's a luxe editor favorite or a modern Western silhouette. We've uncovered a wide range of footwear from reader-favorite brands like Reformation and Sam Edelman to lavish designers like Khaite, Larroudé, and Paris Texas. Below, shop the best pointed-toe boots for winter (and beyond).

The Best Pointed-Toe Ankle Boots

Bid your worn-out booties adieu with a new pair of pointed-toe ankle boots. The short height makes it a comfy shoe for professional events and laid-back occasions year-round. If you're in the market for a worthy investment, consider our team's quiet luxury queen's pick: Khaite The Marfa Ankle Boot.
"Hear me out, I know these are wildly expensive, but there are a few reasons why these boots are personally worth the investment," says Senior Affiliate Strategist Kate Spencer. "First, I am a baggy jean and trouser girl, and these immediately elevate any casual look. Second, a black ankle boot is guaranteed to never go out of style. And finally, there’s some sort of magic worked into the silhouette of this shoe because they’re flat boots (perfect for an NYC dweller) but elongated because of the slightly squared pointed toe. If you pair them with the right pant, they make you look like you’re wearing a heel! Magic, I tell you."

The Best Pointed-Toe Knee-High Boots

We know knee-high boots are trending, but we recommend not settling for anything other than knee-high pointed-toe boots. The model-esque shoe will instantly upgrade casual 'fits to sophisticated looks. Our fashion director's favorite? Larroudé's Kate Boots.
"Larroudé makes some of the most comfortable heels I have ever worn, and these boots — which come in a bunch of different colors and fabrications — are no exception," raves Fashion Director Irina Grechko. "The toe is sharp enough without being too pointed (a hazard for New York City's cobblestone streets), while the knee-high length is versatile enough to go with everything from midi skirts and dresses to jeans and pants."

The Best Over-The-Knee Pointed-Toe Boot

Whether you're in the mood to try out a show-stopping over-the-knee boot in glistening gold or minimalistic black, we've got styles that'll make a statement with every step. You'll likely only need one of these special-occasion shoes, so shop for the best kind from our list. There are slouchy over-the-knee styles, more fitted ones designed for date nights or GNOs, and comfy wide-leg kinds from brands like Vince Camuto and H&M. Don't be afraid to step out of your comfort zone and into a wildly fun pair of pointed-toe boots.

The Best Pointed-Toe Cowboy Boots

Make it Western but with a modern twist. We're talking about pointed-toe cowboy boots in leather, suede, and mixed fabrics — this isn't any ol' rodeo. These booties have eye-catching details that'll make you want to throw on an oversized jean jacket or your favorite jeans and dance. Select pairs are decorated with intricate floral embroidery and stitching while others have luxe embossed patterns.

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