What Celebs Were Wearing To Awards Ceremonies In 1999

In honor of our 25th anniversary, we take a look back at 1999’s dreamy awards season style.

The Los Angeles community has long acknowledged Awards Season as a fascinating time of reflection and recognition. With the next few months marking the biggest entertainment industry events, Angeleno revisited the 1999 awards shows—from The 41st Grammys to the 56th Annual Golden Globes—to see what dazzling outfits and decadent jewelry the stars wore in the dawn of the early aughts.

Will Smith & Jada Pinkett 41st Annual GRAMMY Awards; PHOTO BY KMAZUR

Jane Leeves 56th Annual Golden Globe Awards; PHOTO BY RON GALELLA

Usher 41st Annual GRAMMY Awards; PHOTO BY RON GALELLA

The Chicks 41st Annual GRAMMY Awards; PHOTO BY FRANK TRAPPER

Sandra Bullock 25th Annual People’s Choice Awards; PHOTO BY RON GALELLA

Kelly Preston & Ben Stiller 56th Annual Golden Globe Awards; PHOTO BY NBCUNIVERSAL

Angelina Jolie 5th Annual Screen Actors Guild of America Awards; PHOTO BY RON GALELLA

Lucy Liu, Camryn Manheim & Jane Krakowski 56th Annual Golden Globe Awards; PHOTO BY KMAZUR

Eric McCormack & Debra Messing 25th Annual People’s Choice Awards; PHOTO BY RON GALELLA

Rachel Griffiths 5th Annual Screen Actors Guild of America Awards; PHOTO BY RON GALELLA

Steven Tyler 41st Annual GRAMMY Awards; PHOTO BY RON WOLFSON

Ted Danson & Mary Steenburgen 5th Annual Screen Actors Guild of America Awards; PHOTO BY RON GALELLA