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Jessica Biel Reflects on Her Worst Red Carpet Looks in Crazy About Tiffany’s: ‘I Didn’t Know Any Better!’

Jessica Biel
Jessica Biel Axelle/Bauer-Griffin/FilmMagic

Talk about Flashback Friday!

In Crazy About Tiffany’s, a documentary about the famed jewelry store and its impact on pop culture that was released last month, Jessica Biel and her longtime stylist Estée Stanley choose jewels for the 2014 Oscars. But when Stanley pulls out a book of the Bleeding Heart star’s past red carpet outfits, it unveils quite a few … err … diamonds in the rough.

Biel, 34, laughs out loud — and cringes — at some of her gaudier picks in the film.

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“I was 19, you know,” explains the actress, who is married to Justin Timberlake. “No more high-heeled flip-flops and tan lines and crop tops. I didn’t know any better!”

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Biel may be able to poke fun at herself now, but she admits in the documentary that the business of choosing an iconic carpet ensemble is a serious matter.

“It’s fun, but it is intense,” she says. “It’s not to be taken lightly. You’re presenting yourself in a particular way because it is my business.”

Scroll down for some of Biel’s more laughable looks.

Jessica Biel
Jessica Biel Jim Smeal/WireImage

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She hit the 1998 premiere of Halloween H20 with some serious tan lines … and some questionable arm candy. “Look at my watch!” Biel squeaked in the documentary.

Jessica Biel
Jessica Biel The LIFE Picture Collection/Getty

Seeing it through: Biel’s sheer top left little to the imagination. 

Jessica Biel
Jessica Biel The LIFE Picture Collection/Getty

Biel layered on the leather on the red carpet for Playing by Heart in 1998.

Jessica Biel
Jessica Biel Ron Galella, Ltd./WireImage

A leg up! She rocked platform sandals and a tube top at a WB party in 1998.

Jessica Biel
Jessica Biel Jim Smeal/WireImage

Her flower power was in full effect at a 2003 General Motors fete.

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