Leave it to these trendsetting twins to take a questionable in-da-club classic — the body-con miniskirt — and turn it into something stylish that you'd want to wear every day. In the late aughts, the pair frequently wore these tight little skirts with slouchy tees and boyfriend-style button-ups to make them feel less vampy and more relaxed. They often DIY'd the look, too; in an August 2007
Marie Claire interview with Ashley, writer Lucy Kaylin notes, "That black mini she's wearing? It's actually a Wolford bodysuit pulled down — she shows me the strappy part tucked in around her waist, under her shirt." And in a piece on Mary-Kate in
Harper's Bazaar from that same year: "She is wearing a nautical striped T-shirt (her mom's from the '70s), tucked into two black Wolford slips rolled down and turned into a tight, Robert-Palmer-video-style mini." Eventually, they produced a similar style in leather for their line The Row (seen here on Ashley).
Photo: Dimitrios Kambouris/WireImage (L), Ray Tamarra/Getty Images (R)