1999 Emmy Awards fashion flashback

By Gena Oppenheim 8:17am PDT, Sep 3, 2019

We're gonna party like it's 1999… at the Emmys, that is! In honor of the 2019 Emmy Awards on Sept. 22, Wonderwall.com is going back in time to check out what the stars wore on TV's biggest night two decades ago, starting with then-Hollywood power couple Brad Pitt and Jennifer Aniston. Brad looked sexy and laid back in a black suit with his dress shirt unbuttoned at the top, while Jen (who was nominated for her work on the hit sitcom "Friends" that year) dazzled in a brown Randolph Duke gown with a sheer beaded bodice. Keep reading for more fashion flashbacks from the 1999 Emmys!

Calista Flockhart took a risk with a casual-formal combo ensemble at the 1999 Emmys — and it paid off. Her now-iconic Ralph Lauren look featured a simple white button-up shirt tied into a crop top and a canary-yellow chiffon ballgown skirt with a drawstring waist. Both her style and legal drama, "Ally McBeal," were winners that year!

Midriff-baring formalwear was definitely a trend at the 1999 Emmys! Halle Berry wore a pink-beaded Versace tank top with a revealing scoop neckline and a coordinating black tulle skirt. Luckily, she didn't have to accept an award in that bizarre dress: Her first win came the following year for her performance in "Introducing Dorothy Dandridge."

Sarah Jessica Parker, who was nominated for her role as Carrie Bradshaw in HBO's "Sex and the City," went with a mellow yellow look in 1999 for her first time at the Emmys. SJP wore a slinky Anna Molinari slip dress, but don't be fooled by the airy silhouette. Sarah's gown was actually quite heavy as it was encrusted with glittering crystals. "You wanna feel the weight of it?" she joked.

Back in the good old days when "Felicity" was still on the air, the show's shining star, Keri Russell, was every girl's style inspiration. Take the strapless white Armani gown with clean, elegant lines that she wore to the 1999 Emmys, for example. Keri looked relatable yet ultra-chic with the addition of an iridescent lavender shawl draped on her arms.

Julia Roberts has always known how to be a classy "Pretty Woman," especially back in the '90s. She wore a timeless black Ralph Lauren halter gown to accompany her then-boyfriend, Benjamin Bratt, to the 1999 Emmy Awards. Ben, who was nominated for his supporting role on NBC's "Law & Order," didn't look too shabby either in a formal black tuxedo.

The sparkling pink David Cardona gown that Lara Flynn Boyle wore to the 1999 Emmys couldn't have been more different from the modest business attire she wore to play an assistant district attorney on ABC's "The Practice." Her sheer sleeveless number with strategically placed crystal beading didn't leave much to the imagination.

Lucy Liu shut down the 1999 Emmys red carpet in a unique red-and-black number custom made by costume designer Joseph Porro. The nominated "Ally McBeal" star's look featured an asymmetrically constructed neckline and a long, regal train in a bold Asian-inspired print, which popped nicely against her black bodice.

Michelle Williams had a spaghetti-strap moment to remember at the 1999 Emmys. The "Dawson's Creek" starlet donned a simple and sexy pale pink gown with a sheer sequin overlay to add a touch of subtle sparkle.

Sarah Michelle Gellar cleaned up nicely after leaving the set of her hit show "Buffy the Vampire Slayer" to take a walk down the red carpet at the 1999 Emmys. She stunned in a turquoise Vera Wang halter gown with a leg-baring front slit. Even two decades later, SMG says it's still one of her favorite looks, but most of all, she's just "excited it still fits."

Christina Applegate was ravishing in red sequins at the 1999 Emmys. Her spaghetti-strap number by Richard Tyler featured intricate beadwork around the waist and a sexy thigh slit. The "Married With Children" star accessorized with a bright red shawl and a tiny rectangular clutch perfect for the red carpet.

Debra Messing was on hand at the 1999 Emmys to support her NBC sitcom, "Will & Grace," which was nominated for best directing. But she looked like a winner in her own right wearing a strapless cream gown with an asymmetrical hemline and pleated train. She kept it cohesive with a clutch made from the same shimmering silk fabric as her dress.

Gillian Anderson dressed the part of a leading lady in a Prada cocktail mididress at the 1999 Emmys (she was nominated that year for her work on the FOX sci-fi series "The X-Files"). Her champagne number featured a halter neckline, structured corset bodice and all-over floral print featuring pops of color in shades of pink, red, purple and gold.

Leelee Sobieski was just 17 when she attended the 1999 Emmys (she was nominated that year for her leading role in the miniseries "Joan of Arc") and it was pretty clear she was still working on refining her personal style. She wore a plain black gown with a plunging neckline and rectangular-shaped beadwork on the bodice that reminded us of the magic carpet from "Aladdin."

All Portia de Rossi was missing at the 1999 Emmys was her broomstick! The "Ally McBeal" actress gave off major witch vibes in a distressed black dress with a deep-V neckline and extra-frayed hemline. The addition of knee-high boots with a pointed toe didn't help matters.

Jane Krakowski, who also starred on "Ally McBeal," looked radiant and polished in a violet Fause Haten mermaid gown the 1999 Emmys. She paired the strapless silk number with a dainty floral cross-body clutch that matched.

Helen Mirren dressed like a true winner at the 1999 Emmys in a stunning Badgley Mischka gown (she took home an award for best lead actress for her work in the TV movie "The Passion of Ayn Rand"). Her dusty blue dress featured a square neckline and darker velvet fabric from the waist down, all tied together with shimmering crystals dripping down the bodice and sheer long sleeves.

"ER" star Julianna Margulies ditched her on-screen scrubs for much sexier duds at the 1999 Emmys. She looked ravishing in a strapless red silk corset dress that hugged her in all the right places.

Helen Hunt kept it simple in a strapless black number at the 1999 Emmys, where she won big for her performance on NBC's rom-com series "Mad About You." Her A-line gown featuring a unique layered side train was classic and elegant.

Jane Leeves' sitcom, "Frasier," received a total of eight nominations at the 1999 Emmys, but judging by her revealing Randolph Duke dress, she wanted all of the spotlight! Her totally sheer number, which was drenched in pink sequins, featured a low draped neckline and a daringly high side slit with a bow at the top.

Cynthia Nixon went with an interesting color combination at the 1999 Emmys. The "Sex and the City" star wore a sleeveless pastel green top with a billowing sherbet orange skirt, both in the same iridescent silk fabric.

Courtney Thorne-Smith stood out from her ensemble cast on "Ally McBeal" in a dazzling deep blue gown at the 1999 Emmys. Her sleeveless boat neck number featured rows of jewel-encrusted flowers throughout.

Patricia Heaton opted for a surprising two-in-one white ensemble at the 1999 Emmys. The "Everybody Loves Raymond" actress wore a floor-length patterned tunic top that buttoned at the waist but could be opened to reveal a coordinating pencil skirt underneath.

Sela Ward looked a bit medieval in a boisterous purple Chanel ensemble at the 1999 Emmys. She wore a strapless sequined burgundy dress with rectangular block lines and a puffed-sleeve lilac overcoat that tied around her waist.

Kristin Davis tried to jazz up her simple black gown at the 1999 Emmys by adding a crocheted white belt loosely tied around her waist. The "Sex and the City" star's strapless number also featured a white lace undercarriage that peeped out from the bottom.