1 / 17

Britney Spears and Justin Timberlake wearing matching denim looks to the 28th annual American Music Awards in 2001.

(Photo: Frank Trapper/Corbis via Getty Images)

From Daisy Duke to Britney Spears, the Best Denim Fashion Moments of All Time

Denim Week is almost over, and to close it out, here’s a look back at the most noteworthy denim pop-culture moments.

Some are more cringe-worthy than others. For starters, there’s that time Justin Timberlake and Britney Spears showed up on the red carpet of the 2001 American Music Awards wearing head-to-toe matching denim looks.

Over on the small screen, the casts of Beverly Hills, 90210 and Saved by the Bell favored baggy, light-washed, tapered-style jeans. What seems retro today was high-style at the time.

As for some majorly sexy moments, there’s Daisy Duke from the The Dukes of Hazzard, who wore a pair of very low-cut denim shorts, as did Cindy Crawford in an iconic Super Bowl TV ad for Pepsi in 1992.

Click ahead in the gallery above to scope out the greatest denim moments of all time.

Read more from Yahoo Style + Beauty:

The Top 5 Favorite Denim Brands in the Fashion Industry
6 Crazy Denim Styles to Know About This Summer
Priyanka Chopra, Yara Shahidi, Wiz Khalifa, and Friends Star in New Gap Video

Follow us on Instagram, Facebook, and Pinterest for nonstop inspiration delivered fresh to your feed, every day. For Twitter updates, follow @YahooStyle and @YahooBeauty.