From 2006 to 2020, Ashley Benson Critiques Her Fashion Evolution

"Oh God!” Ashley Benson nearly falls backward when we show her a red carpet photo from 2006. It’s the summer premiere of Monster House and she is wearing a black lace camisole, pleated mini skirt, and black pumps. A long knotted pearl necklace and marbled pink resin cuff finish the look. It’s a far cry from the elevated style we’ve come to know and love of Benson in recent years, but hey, it was 2006 and what was considered "in fashion” was very different back then, so let’s cut her some slack. 

I'm playing one of my favorite Who What Wear games with the actress, Would You Wear It Now, via Zoom and getting the back story on some of her favorite (a gorgeous Hugo Boss coat worn as a dress) and not-so-favorite (a button-down chambray Zara number) looks from the past 14 years. And while she’s had quite the fashion evolution, one thing that has never changed for Benson is her impeccable taste in eyewear. Whether it’s a classic aviator, something more modern, or a sleek round style, she knows good sunnies. So much so, in fact, she became a founding partner of the eyewear brand Privé Revaux. And she, along with fellow actor Matt Bomer, are the brains behind Privé’s latest capsule collection, a gender-neutral line featuring five new designs. 

The first-time collaboration is available online now and just in time to take a fun walk down fashion memory lane with the Pretty Little Liars star, so check out the video below and shop the Bomer x Benzo collection.

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Shop the Privé Revaux Bomer x Benson Collection.

Next Up: Hilarie Burton Takes the Would You Wear It Now Challenge

Executive Director, Entertainment

Jessica Baker is Who What Wear’s Executive Director, Entertainment, where she ideates, books, writes, and edits celebrity and entertainment features.