Ariana Grande vs. Khloé Kardashian: Who Rocked Tom Ford Over-the-Knee Boots Better?

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Back in 2014, Ariana Grande made a daring statement at the MTV Video Music Awards in an exceptionally hot pair of Tom Ford over-the-knee boots.

Just a year earlier, Khloé Kardashian had stepped out in another striking pair from the same designer, proving Tom Ford’s bold boots were a must-have among Hollywood’s style-setters of the era.

Ariana Grande Rocks Tom Ford Over-the-Knee Boots at the 2014 MTV Video Music Awards

Judging by the look of her skintight black leather ensemble at the 2014 MTV Video Music Awards, the red carpet wasn’t the only thing Ariana Grande was working.

With her hair slicked into a long, high ponytail, the pop star — who opened the show alongside Jessie J and Nicki Minaj (wardrobe drama and all) before performing “Break Free” in yet another pair of towering boots — leaned fully into biker-chic glamour.

Ariana Grande turned heads at the 2014 MTV VMAs in a strapless Moschino leather mini dress paired with Tom Ford over-the-knee bootsAriana Grande turned heads at the 2014 MTV VMAs in a strapless Moschino leather mini dress paired with Tom Ford over-the-knee boots

She hit the red carpet in a strapless bustier and matching mini skirt from Moschino’s Resort 2015 collection, cinched with a chunky logo belt, and grounded the daring look with Tom Ford’s $2,950 nappa stretch leather metal stiletto over-the-knee boots.

Finishing touches came courtesy of Borgioni’s 18K black rhodium gold, black diamond fleur-de-lis stud earrings, her now-signature half-up ponytail, and a matte red lip that sealed the tough-girl punch.

Ariana Grande completed her edgy look with a Moschino logo belt, bold zippers, and sleek straight hair tied in her signature high ponytail at the 2014 MTV Video Music AwardsAriana Grande completed her edgy look with a Moschino logo belt, bold zippers, and sleek straight hair tied in her signature high ponytail at the 2014 MTV Video Music Awards held at The Forum in Inglewood on August 24, 2014 (Credit: Joel Ginsburg / DJDM / Judy Eddy / WENN / FayesVision)

Khloé Kardashian’s Bold Tom Ford Boots at Kim Kardashian’s 33rd Birthday Party

Standing tall at 5 feet 8.5 inches (174 cm), Khloé Kardashian towered over her 5-foot (152.4 cm) sister Kourtney as she paired Tom Ford’s geometric patchwork over-the-knee boots with a curve-hugging Hervé Léger bandage mini skirt.

Khloé Kardashian posed alongside sister Kourtney at Tao Nightclub, wearing a plunging black mini dress with Tom Ford geometric patchwork boots at Kim’s 33rd birthday party at TAO NightclubKhloé Kardashian posed alongside sister Kourtney at Tao Nightclub, wearing a plunging black mini dress with Tom Ford geometric patchwork boots at Kim’s 33rd birthday party at TAO Nightclub in Las Vegas on October 25, 2013

The reality star amped up her look with layered gold necklaces and voluminous wavesThe reality star amped up her look with layered gold necklaces and voluminous waves

Tom Ford’s Geometric Patchwork Fur Over-the-Knee Boots, originally retailing for $3,450, featured luxe suede and pony hair panelsTom Ford’s Geometric Patchwork Fur Over-the-Knee Boots, originally retailing for $3,450, featured luxe suede and pony hair panels

Why Celebrities Love Tom Ford Boots

Rather than asking who wore them best, it’s clear that Tom Ford’s over-the-knee boots have become a red-carpet staple for stars like Ariana Grande, Khloé Kardashian, Rihanna, and Gigi Hadid.

Celebrities gravitate toward Tom Ford footwear because it blends prestige, distinctive design, and unmatched craftsmanship — making every pair a symbol of modern luxury and sophistication.

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