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On Point! 5 Pointed-Toed Boots That Are Fashion-Forward and Pain-Free

pointed-toe boots

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Now that it’s almost November, it’s time to gear up for the colder weather ahead. We need to bundle up from head to toe! That means switching up our shoe style — ballet flats, mules and clogs are no longer cutting it. But just because we’ll be living in boots for the foreseeable future doesn’t mean we have to sacrifice fashion for warmth. On the contrary! The right boot can instantly elevate your ensemble. Our favorite silhouette? Pointed-toed boots.

We know what you’re thinking — pointed-toe boots can pinch your feet, making any movement painful. But we tracked down five options from Zappos that are just as comfortable as they are flattering and fashionable! We even included reviews as proof. Elongate your legs and upgrade your winter wardrobe with these pointy picks!

Mark Fisher LTD Ankle Booties

Mark Fisher booties

This Chelsea-style ankle bootie is your new everyday essential! Featuring a pointed toe with a metal cap for extra elegance and a lightly padded footbed for extra comfort, this leather boot is the best of both worlds. Even the 1.5-inch block heel gives you a slight lift without throwing you off balance. According to satisfied shopper, “These boots are AMAZING. I think they may be the best boots I’ve ever owned, no joke. The inside is slightly padded and they’re really easy to get on and off.”

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FARYL by Farylrobin Suede Tall Boots


Crafted from suede leather, these tall boots are the epitome of sophistication. One reviewer gushed, “These boots are perfect! The heel is comfortable but dressy-looking. The suede is butter soft.” And another customer shared, “Fit was perfect for me and that is saying something because of bunion issues. Very comfortable and great style also. Look more expensive than they cost.” Style these pointed-toe boots with flowy maxi dresses and mini sweater dresses all season long!

Was $190You Save 8%
On Sale: $175
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Steve Madden Western Booties

Steve Madden booties

If you want to try the western trend without going full cowboy boot, these heeled booties are a good place to start. Available in five neutral shades, these Steve Madden shoes will match almost any outfit. Team these pointed-toe boots with skinny jeans for the office, and then dress them up with a mini skirt on a night out! One shopper declared, “Great quality and are comfortable despite the heel height!”

Was $140You Save 26%
On Sale: $104
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Sam Edelman Stiletto Booties

Sam Edelman stiletto heels

Step up your shoe game (literally) with these sky-high stiletto booties! Featuring a four-inch heel and pointed toes, these boots are made for strutting! One customer called these Sam Edelman shoes “beautiful, sexy, and comfortable! I could wear these all day with no break-in time and be fine.”

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Schutz Embossed Tall Boots

Schutz snakeskin boots

Shoot! We may just need to splurge on these Schutz boots. Available in black or green crocodile print and snakeskin, these tall boots are sexy and stylish. “BEST BOOTS EVER!!!!” one reviewer raved. “I am SO HAPPY that I bought these. They’re gorgeous in person, and so so comfortable.” Team these tall boots with a little black dress for date night!

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fall boots

Related: Fall Fashion Forecast: These Boots Are Made for Walkin’

Looking for additional boot recommendations? Check out more picks below:

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