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The star attended the 2nd Annual Martini Shot Mentor Awards in 1999 while wearing a red furry bag and a mohair cardigan. The colorful accessory added a pop of color to her all-black ensemble — a look she still sticks to today.SGranitz/WireImage
Aniston arrived to the Avo Cinema Center for the premiere of director Ivan Reitman's film 6 Days, 7 Nights in 1998. She traded in a fancy red carpet gown for a more dressed-down look consisting of cuffed blue jeans, sandals, and a button-down shirt.Frank Trapper/Corbis via Getty Images
The actor attended the Fight Club Los Angeles Premiere in 1990, accompanied by her then-boyfriend Brad Pitt. To suit the occasion, she wore an all-black outfit (check out the front slit detail on her top) and carried a dazzling bucket bag.Barry King/WireImage
In 1998, Aniston showed up to the red carpet for The Object of My Affection in NYC. Once again, she went for an all-black look — this time it was comprised of a strapless midi dress, a shrug cardigan, a pochette bag, and a pair of open-toe stilettos.Ron Galella, Ltd./Wireimage
While on set for The Object of My Affection in 1997, Aniston wore a striped oversized jumper, a pencil midi skirt, and a pair of Mary Janes. All these pieces still exist in our wardrobes today.Mitchell Gerber/Corbis/VCG via Getty Images