Jenna Lyons's look is practically synonymous with J.Crew, the brand where she's worked for almost her whole life. A rangy, six-foot-tall brunette with a fondness for thick-framed tortoiseshell glasses and pink lipstick, her penchant for menswear-inspired outfits with feminine, edgy touches (sparkly bracelets, hot pink nail polish) have sparked a generation of J.Crew worshippers. Her trademark looks include mixing prints and bright colors with tomboyish pieces like chambray shirts and beat-up jeans; while she's always pushing the envelope with prints and color combinations, she always sticks to streamlined, close-cut silhouettes. Enjoy a look back at her outfits through the years in our slideshow.