Chelsea Handler Teams Jason Wu Dress With Thigh-High Boots to Celebrate 50th Birthday in NYC
Chelsea Handler has been making the rounds on the New York City morning show circuit in promoting her seventh book, “I’ll Have What She’s Having.”
The comedian stopped by “Good Morning America” and the “Today” show, where she discussed the book of essays, as well as turning 50 (it happens to be her birthday today), her podcast, and more. In between appearances, she was seen waving to fans on the streets of New York City. Handler wore a chic midi dress with thigh-high boots.
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The former late-night talk show host opted for a tan Jason Wu dress featuring short sleeves and an asymmetrical draped neckline with a contrasting black ribbon detail. It’s currently marked down from its original price of $2,495 on saksfifthavenue.com. The romantic, figure-hugging dress also boasted a steep side slit that drew attention to her black over-the-knee boots.
The boots she reached for appeared to be crafted in velvety suede with stretchy shafts and featured an elongated pointed toe. The style was complete with a medial side zipper and a skinny low heel measuring approximately 3 inches. Many brands on the market offer similar styles, including luxury brands like Gianvito Rossi, Khaite, Paris Texas, Stuart Weitzman, Le Silla, and more.
Thigh-high boots have long been a staple in many celebrities’ wardrobes. Just about everyone has stepped out in a pair, from Rihanna to Princess Beatrice to Heidi Klum. The sultry style comes in a wide range of designs, from slouchy styles to platform versions to crystalized options.
Earlier this month, Handler served as the host of the 2025 Critics Choice Awards, where she had five outfit changes. The “Chelsea Lately” alum first hit the carpet in a cream-colored midi dress featuring an asymmetrical neckline and ruffled accent paired with mesh Betsey Johnson stilettos embellished with pearl studs and rhinestones in a lattice pattern. The pointy d’Orsay style is available to shop on the brand’s site for just $129. See her outfit, and others, at the Critics Choice Awards via the gallery below.
For her “Today” show appearance, she styled a royal blue dress with pointy beige stiletto pumps. “I’ll Have What She’s Having” is out today.
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