This morning’s Wall Street Journal says it all: “Plaid Taste: The Return of Preppy.” As if we weren’t already aware of it, Preppy, the most exuberant expression of classic style, is back on the fashion radar in a big way. Washington, D.C., never really lost its affinity for the preppy lifestyle. It fits very well with the power and class aspirations that feed daily life here.
While we have multiple Brooks Brothers and no less than three Ralph Lauren outlets serving the financially flush neighborhoods of Georgetown, Tysons, and Chevy Chase, we also have Sherman Pickey, a literal shrine to the prep ethos. The nation’s capital is also home to J. Press, the touchstone of true New England prep. If you ever get over to Saint Michaels on Maryland’s Eastern Shore, a very preppy vacation address, check out Sailor on Talbot Street. It is stuffed to the gills with offerings from Vineyard Vines to Lilly Pulitzer.
In its most traditional form, preppy style actually toned down the greens, pinks and reds to a respectable old-money, sun washed, had-this-polo-forever feel. The idea was always to celebrate the seaside, wind in your hair summer lifestyle, but to do so in an understated way. Today’s preppy is more or less the opposite. It’s big, it’s bright, and can cover every part of your body. From Nantucket Reds canvas pants and whale belts to ribbon watch bands and monogrammed multicolor boat bags, some people literally overdose on the look.
When it comes to dressing in an authentically preppy manner,more may be better but too much is just plain tacky. It’s the difference between someone wondering if you actually have a beach house and just laughing at you. Have fun with preppy style but don’t try and do it all at once. By all means, use the Preppy Handbook as a tongue-and-cheek guide, but don’t mistake it for a textbook.
Looking for a role model? Try Jack Kennedy, someone who had a naturally preppy look. Yes, he grew up with a monogrammed silver service in his mouth, but he also embodied an approachable preppiness. While JFK always looked fresh off the yacht, nothing ever looked too contrived or overdone.
Build on that understated style by adding shots of color or pattern. Like a ribbon belt that picks up the colors in your shirt or tie. Lose the socks when wearing loafers or docksiders. For classy casual look, pair well worn khakis with a blue blazer and un-ironed oxford. Dress it up for dinner at the club by switching to a tailored dress shirt with french cuffs and signal flag cuff links. Pick one or two elements to highlight: the repp tie in your school colors on a checked shirt, the pants liberally covered with golden retrievers, or a Kelly green watch band. Just check yourself in the mirror before walking out the door and make sure you don’t look like a mannequin.