Rachel Roy Really Hopes No One Has Photos of Her Wearing These

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Comedy writer Bonnie Datt once bought a chainmail vest "for clubbing"—a purchase she later came to lament, once she realized that chainmail wasn't particularly slimming. Inspired by this, she now spends her spare time asking famous people to dish about purchases which they initially loved—but ended up regretting, for Buyer's Remorse.

Californian-born designer Rachel Roy is talented, gracious, and—when you see her up close—even more beautiful than any of her models. The former stylist's eponymous line has only been around since 2005, but Roy has already dressed everyone from Oprah Winfrey to First Lady Michelle Obama. Unlike many designers we've spoken to, who insist they've "never" had Buyer's Remorse, Rachel was very forthcoming with a charming story about a teenage fashion choice gone embarrassingly wrong...

Racked: Can you tell us about something you've had Buyer's Remorse about?

Rachel Roy: I'm a fashion girl and I have been since the first kind of cognitive thought that I ever had. So I've bought and tried so many different things. And I've made so many different mistakes.

Racked: Do any early ones stand out?

Rachel Roy: Yes. I've always been tall so I had to wear boys' jeans. So that's what got me into vintage shopping quite quickly, because I didn't literally want to wear new boys' jeans. So I thought I was really cool wearing Levi's 501 Button Flies, and then I saw George Michael doing that in Wham. So I was super happy with that. But even those weren't long enough, so I had to roll them. And then at the time I didn't know it was okay to show ankles, so I would do those socks—those white scrunchy socks. I really hope there's no pictures of those anywhere.

Racked: So you regret the jeans or the socks?

Rachel Roy: It would be the socks. The socks were the mistake, not the jeans. Those are really still the only jeans I wear. I love them.
· All Buyer's Remorse Posts [Racked]
· Rachel Roy [Official Site]