1999 People's Choice Awards - Fashion flashback | Gallery

By Bryanne Salazar 8:10am PST, Nov 5, 2019

On Nov. 10, 2019, the E! People's Choice Awards returns. In honor of the 45th anniversary of this award show that lets fans choose the winners, Wonderwall.com is taking a walk down memory lane to see what popular celebrities were wearing on the red carpet two decades earlier at the 25th Annual People's Choice Awards in 1999… starting with the lovely Christina Applegate. The "Married… with Children" actress — who won the award for favorite female performer in a new TV series for her work on the sitcom "Jesse" that year — rocked a feminine black of-the-shoulder gown featuring a subtle see-through bodice and full skirt, Christina paired the look with two-toned hair, a silver-trimmed clutch and a ribbon choker. Keep reading for more flashback fashion moments from the 1999 People's Choice Awards…

Given what a fashion icon Celine Dion is today, it's almost surprising how demure her look was at the 25th Annual People's Choice Awards: The favorite female performer winner arrived in a short-sleeved gray sweater paired with a black ballgown skirt.

"Mad About You" star Helen Hunt took zero fashion risks in this simple black slip dress. Keeping her decollete bare, Helen — who won the People's Choice Award for favorite female performer that night — accessorized the look with black strappy sandals, diamond drop earrings and a matching cuff bracelet.

While black was certainly the color of choice that night, we love how Sandra Bullock worked a floral print into her 1999 People's Choice Awards style. Her beaded off-the-shoulder bodice gave way to a colorful flowered skirt with a black chiffon overlay. Sandra — who won the award for favorite motion picture actress that night — kept her sculpted shoulders and decollete bare, choosing only earrings and a sheer black wrap as her accessories for the night.

"Will & Grace" star Debra Messing was so extra at the 1999 People's Choice Awards, and we absolutely loved it. From her curly bouffant hair to her elaborately beaded nude and black gown featuring a fluffy fringe hemline to her embellished pointy-toe heels, Debra wasn't afraid to bring it, and we mean all of it, to the red carpet.

Debra Messing's "Will & Grace" co-star Eric McCormack took a much more subdued approach to his fashion at the 1999 People's Choice Awards. Standing beside wife Janet Holden (who looked lovely in a white satin gown), Eric wore a simple black tuxedo adorned with a red ribbon to support HIV/AIDS awareness.

"Frasier" star Kelsey Grammer went classic with a black tuxedo at the 1999 People's Choice Awards. We do like the fact that he swapped out a traditional black bow tie for a silky white one, giving him a little more style drama. His then-wife, Camille Grammer, flaunted her stellar curves in a figure-hugging green velvet off-the-shoulder gown and sparkling diamond necklace.

Even before duck face was a thing, model-actress Brooke Shields was pursing her lips like a queen. At the 1999 People's Choice Awards, the "Suddenly Susan" actress opted for a backless, high-neck black satin halter dress that showed off her flawless frame. We're not crazy about her fringed shawl, but with cheekbones like those, she can pull off any look.

Former "Access Hollywood" host Nancy O'Dell looked like a Victorian lampshade at the 1999 People's Choice Awards. Her Nicole Miller look — a black-and-nude see-through dress with sheer beaded lace panels and lots of dramatic fringe — certainly stood out on the red carpet.

"Sabrina the Teenage Witch" star Melissa Joan Hart was just 23 at the 1999 People's Choice Awards. Her black spaghetti-strap midi-length dress wasn't necessarily bad, but combined with her accessories and hairstyle, it did make her look older than her years.

Is it just us or did "ER" star Noah Wyle's tuxedo look two sizes too big on him? While Noah swam in his black tux, his makeup artist then-wife, Tracy Warbin, looked lovely in a beaded pale seafoam green gown. The only thing we don't love about her look are those open-toed chunky black sandals, which are almost jarring against the soft elegance of the dress.

At the 1999 People's Choice Awards, "Titanic" actress Gloria Stuart was a vision of loveliness and laughter in this flowing ensemble. Matching her tropical-print duster and skirt with a solid navy blouse and gorgeous seashell statement necklace, Gloria looked ready to sail away into the sunset.

Favorite male television performer winner Tim Allen and his then-wife, Laura Deibel, were complementary in their all-black fashion at the 1999 People's Choice Awards. The "Home Improvement" star was one of the few men that night to wear a long tie instead of a bow tie with his tuxedo, which in a night of matching black suits was a nice individualized touch. We've got no complaints about Laura's satin gown or her gorgeous diamond necklace and earrings, which added the perfect amount of sparkle to her style.

"Stepmom" star Susan Sarandon's metallic dress wasn't a winner at the 1999 People's Choice Awards. Somehow, it looked both too tight and too loose at the same time, which is a feat we didn't know a dress could achieve.

While we're grateful TV personality and actress Lisa Canning missed the all-black attire memo, we're not sure we're in love with this blue chrome look. Wearing a quilted baby blue satin slip dress and a matching fur-lined duster, Lisa definitely shined, but she also looked like she was wearing a nightie from Frederick's of Hollywood.

"Baywatch" star David Hasselhoff stood out on the 1999 People's Choice Awards red carpet thanks to his high-collared black-and-white Mandarin-style tuxedo. His then-wife, actress Pamela Bach, perfectly coordinated her look with his in a black satin slip dress and black-and-white shawl.

While we utterly adore late British actress Lynn Redgrave, we wish someone had helped her find a more flattering dress for the 1999 People's Choice Awards. Lynn's silver chemise had a doily vibe, and its matching sheer duster and those ballet flats did nothing to help.

Amongst a sea of black dresses at the 1999 People's Choice Awards, "Frasier" star Jane Leeves looked like a shiny pearl in this gorgeous beaded champagne slip dress. Pairing the glitzy gown with a soft chiffon shawl and pink sandals, Jane evoked Aphrodite-inspired glamour.

Brazilian-American actor Bruno Campos looked like a total hottie in his tuxedo at the 1999 People's Choice Awards. His girlfriend of the time, actress Paula Marshall, looked every bit the '90s star in her sleeveless black gown and sheer red chiffon wrap blouse accessorized with a choker.

The one thing we loved about the nude evening gown that "Titanic" and "Becker" actress Frances Fisher wore to the 1999 People's Choice Awards was how it made her brilliant red hair stand out like a flame. The folded satin bust and elongated train also gave the otherwise boring gown a bit of added intrigue.

We hardly recognized curly haired "ER" actress Alex Kingston at the 1999 People's Choice Awards. From her perfectly smoothed and coiffed 'do to her stunning chocolate-colored beaded evening gown with a matching shawl, Alex traded her TV doctor's scrubs for some major Old Hollywood glam.

Actress Natasha Gregson Wagner — the daughter of Hollywood stars Natalie Wood and Robert Wagner — kept it casually elegant at the 1999 People's Choice Awards in a cowl-necked burgundy halter gown and floral-print shawl.

We're not sure how we feel about actress Patricia Wettig's charcoal and gray gown at the 1999 People's Choice Awards. On one hand, she's clearly feeling beautiful — which is always a gorgeous look — but her lace-up, striped velvet bodice was an awkward match to the voluminous micro-print skirt, giving her a confusing half-undressed schoolmarm-meets-renaissance fair appearance that left us wishing she'd worn something a little more chic.

There is nothing not to love about "Murphy Brown" actress Faith Ford's sexy tuxedo jacket-inspired evening gown at the 1999 People's Choice Awards. The relatively simple look featured a deep neckline and lots of leg, which Faith expertly accessorized with strappy heels, a small clutch and a gorgeous starfish gemstone brooch.

When they go dark, former "ER" actress Kellie Martin goes light. Kellie showed off her enviable curves in a stunning white satin spaghetti-strap gown from Richard Tyler at the 1999 People's Choice Awards. Also worth a mention are Kellie's silver strappy heels and floating pearl necklace, two style choices that weren't necessarily trendy in the '90s but gave her a timeless elegance.