7 Oscars Dresses from the Late 90s and Early 2000s Worth Revisiting

We often remember the show-stopping dresses, but these 7 Oscars dresses from the late 90s and early 2000s (Y2K as Gen Z calls it) deserve to be appreciated too. They may not have led to a “moment” like Michelle Williams in canary-yellow Vera Wang at the 2006 Academy Awards, and they may not have been caught in a “moment,” like Jennifer Lawrence’s Dior Haute Couture gown at the 2013 awards when she fell on the stairs, but the dresses that don’t make retrospective Best Oscars Dresses lists aren’t all forgettable. In fact, many were ahead of their time, and you can see that the seeds for future iconic looks were planted in the less outrageous designs.

These Late 90s and Early 2000s Gowns From Oscars Past May Make You Rethink Your Favorites.


Kate Winslett in 1996 wearing a Vivienne Westwood dress that is pink with a corset top and wrapped fabric in a Grecian statue style

1. Kate Winslet, 1996

At the Oscars where 20 year-old Winslet celebrated her first nomination for Sense and Sensibility, she wore a bright pink gown by Vivienne Westwood, in the signature corset.

Reese Witherspoon in a vintage Dior dress that's champagne colored with sparkle embellishments in an A-Line cut

2. Reese Witherspoon, 2006

Witherspoon wore a Christian Dior gown from 1955 to the 2006 awards, proving that she was ahead of the vintage dress trend that stars like Zendaya often rock today.

Halle Berry in 1996 wearing a lavender Valentino gown that has satin overlaying a fitted dress as if draped on it.

3. Halle Berry, 1996

During the same year that Winselt wore a bubblegum gown, Berry embraced a solid color dress designed by Valentino. Rather than mixing colors, this dress mixed fabrics, which paid off considering how gorgeous Berry looked.

Cate Blanchett showing her back on the red carpet which is bare with gold chains draped down and around it, attached to a strappy tight black dress.

4. Cate Blanchett, 2000

The epitome of Y2K fashion, Blanchett wore the era’s most defining designer: Jean Paul Gaultier. It wasn’t a mesh graffiti-designed top though, as she stunned in this back-bearing bedazzled beauty.

Nicole Kidman wearing a layered silk chiffon light pink/white Chanel gown

5. Nicole Kidman, 2002

The best Nicole Kidman worn at the Academy Awards dress was this Chanel frock in 2002. While the bright red dress Kidman wore to the 2007 Oscar Awards is widely celebrated still today, this more muted gown shows such delicate detail, and paired with her gorgeous strawberry blonde hair it’s simply too good to forget.

Keira Knightley wearing a dark brownish-red (like a cabernet) trumpet wrapped Vera Wang gown

6. Keira Knightley, 2006

In a custom cabernet dress by Vera Wang, Knightley makes a solid case for the importance of picking the right color rather than cut. The latter may not boast much creativity, but Knightley chose a color unique enough to make this gown ultra-chic.

Renee Zellweger with her back turned to us wearing a white gown with a big ornate bow on the lower back.

7. Renee Zellweger, 2004

Zellweger primarily wears dresses by Carolina Herrera, but this one takes the cake. The elegance of the train combined with the extravagance of the bow makes for a delightful gown. The level of sophistication displayed clearly surpasses most Best Dress guides’ radars.


Whether or not these dresses — and the celebs wearing them — make Best Dressed lists, they each vary so much from one another that revisiting them should have provided some sense of satisfaction. Not every gown has to be ginormous to have an impact, and some of them don’t even need to bear any embellishments; these 7 prove that.

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