Chokers
Courteney Cox was way ahead of the curve at the 1995 Emmys in a lavender gown paired with a matching choker. Who could have known that necklace trend would have made such a major comeback over a decade later?
Velvet
Sarah Michelle Gellar proved velvet could still be stylish in a slinky, one-shoulder number at the 1997 Emmys. Va-va-voom!
Off the Shoulder
Angelina Jolie wowed in a nude, off-the-shoulder Randolph Drake dress at the 1998 Emmy Awards. Between the gown's low-cut neckline and the high slit, Angie was the talk of the red carpet that year.
Sexy Bed Head
It wouldn't be a proper '90s roundup if we didn't mention Jennifer Aniston and that hair at least once! The Friends beauty skipped sleek and chic at the 1999 Emmys and boasted a head full of perfectly-undone twists and waves that was oh-so-hot.
Sexy Bed Head
Curl power! Sarah Jessica Parker truly let her luscious locks flourish for her first appearance on the Emmys red carpet in 1999 and we can't get enough. What deep conditioner do you use, girl?
Strapless Slip Dress
Keri Russell didn't need any bells and whistles to make a statement at the 1999 Emmys. The actress kept it sweet and simple in a strapless Armani dress.
Strapless Slip Dress
Debra Messing also jumped on the bandwagon at the 1999 Emmys in a clean, minimal dress that skimmed over her figure.
Crop Top
Whoa, mama! Halle Berry has never been one to shy away from taking a risk and she did just that at the 1999 Emmys while flaunting her curves in a flirty, two-piece ensemble.
Crop Top
Calista Flockhart exudes cool vibes at the 1999 Emmys in a yellow skirt and improvised crop top. Not many stars could make a white button-down look this bad-ass on the red carpet.
Metallic
Helen Hunt looked like a walking disco ball at the 1997 Emmys in a metallic-sequined Gucci gown—and we mean that in the best way possible. The actress was a showstopper in the enchanting silver design.