“Plaid comes and goes in cycles, but it never totally disappears,” says designer Tommy Hilfiger. “I think that’s because it is an incredibly chic look when you wear it the right way—think of Jackie Kennedy and her taffeta skirts or Grace Kelly and her plaid shirts. Just remember, there are plaids, and then there are plaids.” Below, Hilfiger shares his tips for wearing the classic pattern.
Find the soft side. Silk lends itself beautifully to plaid because it’s lightweight and feminine and offsets any unwanted lumberjack associations. Wool is the most traditional fabric, but it can be a little stiff—look for a wool that has cashmere mixed in so it flows. You want your plaid to be drapey. It’s also a good idea to look for skirts or dresses that are cut on the bias and maybe have a bit of fringe.
Don’t get earthy. I like crisp, bright colors for plaid—red, green, navy. I really love a red-white-and-blue one. Stay away from dusty, muted shades, like beige, olive green, and brown; they look muddy. Most plaids have a windowpane accent color, which should be white or gold. That’s what will make it look less woodsman-like.
Keep it anchored. Plaids look best next to anything neutral—a plaid blouse with blue jeans or leather pants, a plaid skirt with a shearling or suede coat. I always think of plaid as perfect for Aspen or a ski town; it’s cozy and outdoorsy. Just don’t get too into the Western thing. Too much turquoise jewelry can make it look costumey in a hurry.