In 1990, Aniston nabbed her first major TV role on the small-screen version of Ferris Bueller. She played Jeannie Bueller, who was originally played by her future Friends co-star Jennifer Grey in the movie. The spinoff only lasted for one season, but at least we got this high-waisted jeans, shiny shirt, and tucked in belt combo when the up-and-comer attended an NBC event in 1990. For more of Aniston’s career highlights, Relive Jennifer Aniston’s Last 27 Years in Hollywood, in Photos.
Aniston attended a 1995 screening of the eventual Emmy-winning TV movie Serving in Silence: The Margarethe Cammermeyer Story with fellow Friends cast member Matthew Perry. Her business casual look checks all the mid-’90s boxes: an oversized blazer, a y-necklace, and a fashion backpack.
One thing about the ’90s is that most of its formalwear wouldn’t have been out-of-place at a high school prom. Even this simple, floor-length slip dress Aniston wore to the 1995 GLAAD Awards qualifies, with the added period detail of its teeny, tiny spaghetti straps. For more throwbacks, check out The Biggest ’90s TV Teen Idols, Then and Now.
Visible bras, exposed midriffs, and open-weave sweaters were all the rage in the ’90s. Aniston combined all of those elements (plus another y-necklace!) for this rocker-ish look perfect for a VH1 event in 1995.
We know what you’re thinking: What’s so ’90s about this ensemble, which Aniston wore to the premiere of her 1997 romantic comedy Picture Perfect? But it’s the chunky-heeled sandals that place this otherwise classic look in time. For more celebrity nostalgia sent right to your inbox, sign up for our daily newsletter.
The strapless satin number Aniston wore to a charity gala in 1997 (accompanied by her Friends co-star Lisa Kudrow) was also the silhouette of choice for many a ’90s bride picking out her bridesmaids’ dresses.
Aniston rocked not one but two ’90s sweater trends to the 1997 premiere of Good Will Hunting, topping a grey twinset with a chenille duster. For more on her ’90s look, check out The One Thing Jennifer Aniston Hated About Her “Friends” Haircut.
Aniston (pictured here with Patricia Arquette) has always loved a monochromatic ensemble. This two-piece from the 1998 VH1 Divas Live concert dates itself with its sleek shape and high neck—plus, the smokey eye and natural lip Aniston paired with it.
The rolled-up jeans, the sheer top, the platform sandals—this 1998 premiere look was practically a uniform for stylish women in the ’90s.ae0fcc31ae342fd3a1346ebb1f342fcb
1999: Screen Actors Guild Awards
The late ’90s were all about low-rise everything. (Just look at any photo of Christina Aguilera or Britney Spears from that era.) Aniston glammed up the trend at the 1999 SAG Awards with this low-slung skirt, matching handkerchief top, and illusion necklace.
It was all black again for one of Aniston’s first public outings with now-ex Brad Pitt. For the 1999 premiere of his movie Fight Club, she wore drawstring pants and another midriff-baring top. The bedazzled handbag—another ’90s status symbol—tops off the look. And for more on Aniston and Pitt, check out Matthew McConaughey Has Some Thoughts on “The Heat” Between Brad and Jen.
