Jessica Biel says she wasn't always a red carpet rock star: "I didn't know any better!"

By catherinekast
Updated March 22, 2016 01:00 PM

If it seems like wearing high-fashion gowns and dazzling diamonds comes second nature to Jessica Biel these days, that wasn’t always the case. In the new documentary Crazy About Tiffany’s (available on demand now), Biel looks back at some of her ensembles from the late ’90s while trying on gorgeous jewels for the 2014 Oscars.

In the days before she worked with her stylist Estée Stanley, Biel rocked all sorts of outfits on the red carpet: We’re talking flared jeans with super-chunky platforms and, to Stanley’s chagrin, a hair elastic around her wrist. “I was 19, you know,” Biel says in the film. “No more high-heeled flip-flops and tan lines and crop tops [now]. I didn’t know any better!”

These days, Biel is one of Tiffany & Co.’s go-to gals on the red carpet. Says the brand’s design director Francesca Amfitheatrof, “Jessica’s amazing. She has that mixture of glamour, which can go back to another time, but she’s also very contemporary.” Check out three of her most memorable Tiffany Blue Book collection moments below.

Dimitrios Kambouris/Getty

The dramatic set she ended up picking out in that scene was for the 2014 Oscars (above). With her Chanel Haute Couture gown, she wore Art Deco-inspired platinum-and-diamond earrings, a necklace and three bracelets, including one featuring her own birthstone, aquamarine. But even though the end result is flawless, the process of picking out the jewels for big events isn’t always like playing dress-up. “It’s fun, but it is intense because it’s not to be taken lightly,” she says. And that’s because “presenting yourself in a particular way” is her job.

We think she’s doing pretty well! At the 2013 Blue Book Ball in New York City she wore a brooch as a hairpiece. It’s worth $115,000 and is inspired by a piece from the French Crown Jewels in the Tiffany archives.

Dimitrios Kambouris/Getty

At the New York City Blue Book launch party in 2014 (below), Biel told us that her knowledge of fancy jewelry didn’t come until recently. “I didn’t really have anything of value for a long time. I bought myself my first pair of diamond earrings when I was a freshman in college,” she said. “That was a big deal. Before that, I grew up wearing lots of friendship bracelets. That was my favorite accessory!” That night she wore a Tiffany Art Deco-Inspired line necklace of round brilliant and baguette diamonds in platinum (below).

Dimitrios Kambouris/Getty

So yes, Biel has come a long way from tube tops and tan lines. Check out the full documentary here, and tell us: Which jewelry ensemble is your favorite on Biel? Are you a fan of the iconic brand?

–Catherine Kast