The iconic G.I. Jane haircut and physique training led her to a tomboy phase during which she favored men’s utility pieces like these denim overalls. But her accessorizing with prayer beads and micro sunglasses gives the look a cool downtown edge that she’s always had.
This is surf chic perfection. This Charlie’s Angels look was a moment in culture that defined the early Aughts — and Moore’s body and crocheted black bikini still inspire us to this day.
This dark silk knee-length dress with three-quarter sleeves is a perfect example of how her style became more polished and high-fashion, which eventually led her to open Fendi couture this week.
The Brat Pack days are full of iconic Eighties fashions. Although this look has a grunge feel, Demi has always been ahead of the trends and this plaid long smock dress with matching jacket looks as cool now as it did then.
This was considered to be one of the worst red carpet moments at the time — and of course now, we’re transfixed by it. This is more of an onstage performer outfit than a red carpet one, but Moore looks incredible in this biker short-meets-Renaissance bustier-meets princess gown ensemble that she designed herself.
This is one of our favorite looks of hers — and very reminiscent of the Donna Karan ad campaigns that she did back in the day. The minimal sleeveless dress with high slit is very much her brand, and also incredibly flattering on her.
This form-fitting knit Missoni dress reads both very early Aughts yet timeless. While promoting Charlie’s Angels, she dominated every red carpet that year. This is a living legacy moment.
This is very L.A. 15 years ago. The wraparound sunglasses, black beanie, hoop earrings, white ribbed tank and Red Bull was everyone who was anyone’s uniform in the weekly magazines. We miss it.
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