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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
A good statement bag can jazz up any outfit. Copy Aniston’s styling trick and get this furry one for yourself.
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
Boyfriend jeans are timeless and easy to style. Dress this one up with a fun top à la Chrissy Teigen or style with your basic tee.
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