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It appears that Anne Hathaway has moved so far beyond wearing no bottoms that she’s now pulling out slightly controversial retro pant styles to incorporate into her off-duty looks. Because after parading around in nothing but Valentino tailoring, the actress was spotted in New York City on Monday wearing not one, but two pairs of early aughts styles.

Hathaway’s first daytime look (spoiler: she had three total) for Live With Kelly And Mark! came in the form of a flashy white set from Des Phemmes that was accentuated by statement cargo pants. Their tailored fit was accented by two exposed pockets on either leg. She styled the throwback piece with a silver rhinestone and white tank top as well as a coordinating button down shirt that she left open. And while many would venture to pair the cargo style with a chunky boot or sneaker, Hathaway complimented them with towering silver Jimmy Choo heels. For accessories, the actress opted for Bulgari jewels, tortoise sunglasses, and layers of silver rings.

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Later during her busy day (she’s currently in the middle of promoting her new critically-acclaimed indie film, Eileen) Hathaway switched into a more comfortable style for The Drew Barrymore Show. The 41-year-old continued her pants streak with mid-wash, wide-legged dad jeans that she, naturally, paired with chunky dad sneakers. Up top, the actress kept things simple with a slouchy gray sweater (courtesy of Barrymore) and carried an Hermès Birkin. Things didn’t end there, though. In between her two appearances, Hathaway treated us to a slight switch up where she offered a more leggy look.

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The star went full business chic in a strapless mini dress that she topped off with a cut-to-perfection double-breasted blazer from Anna Quan. Hathaway kept the same Bulgari pieces but changed things slightly via Louboutin pumps and sleek black sunglasses. Hathaway’s varying degrees, and lengths, of pants prove that even as temperatures continue to cool down, she’ll always keep us guessing.

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