3 Takes on Preppy Style

If “preppy” isn’t one of the words you would use to describe your personal style, then the notion of dressing that way might feel intimidating. But you don’t have to go full-on Gossip Girl with it. You can take a more restrained approach, one that incorporates pieces you wear regularly—say, your favorite pair of jeans—so that the look feels authentic rather than contrived. Here, three ideas to get you started.

SPORTY

We’ve seen rugby shirts on the runway for several seasons now—most notably at Dries Van Noten and The Row—and they are an extremely beginner-friendly way to dip your toe into the preppy pool. We’re fond of this colorful Mongolian-cashmere one: Wear it casually (with jeans and sneakers for school drop-off or a weekend soccer game) or more traditionally, with penny loafers and a polished handbag.

CLASSIC

This is, admittedly, an approximation of an outfit that Gwyneth wore to the office recently. We love the contrast between the super smart upper half (she buttoned her shirt all the way to the top) and the more-casual bottom half—it creates a cool, balanced look we will definitely be copying.

NAUTICAL

Cable-knit cardigan, white denim, leather moccasins, mariner-link ring—this is the look of someone who uses “summer” as a verb and keeps her boat keys clipped to her Miu Miu keychain all year round. Round it out with a pair of sunglasses and a scarf that’s big enough to cocoon yourself in.