Ed Westwick’s Gossip Girl character, Chuck Bass, is the current It boy of the pomo-prepster look. His winning fashion formula? Three-quarters clothing and one-quarter attitude. While his classic trench with royal-blue lining, camel cardigan layered over a plaid shirt and brick-red khakis may be overkill for 80°, the elements are spot-on for guys aiming to bring out their inner postcollegiate prep without looking like a throwback to the '80s. Want the look? Keep reading...
This BR Monogram double-breasted, belted trench from Banana Republic ($350) is classically styled yet fresh. Made of lightweight fabric in a summer-friendly cream color and cut in a slimmer fit, this prepster staple is a great tailored topper for the office and on weekends.
You don’t necessarily need a healthy dose of irony to pull off Polo Ralph Lauren's slim-fit chino in skipper red ($98). They may be bright, but with their trim shape and flat front these casual pants actually read as neutral as opposed to Nantucket.
For warmer weather, opt for a light-colored pattern on a white background, such as Penguin's Shell Rock button-down ($89). A slim fit and snaps on the cuffs—plus that icon of laid-back retro cool, the Original Penguin, on the pocket—keeps this shirt on the postmodern side of preppy.
You don’t actually have to be a prep school student—or play one on TV—to carry this dressed-down ensemble. Blake Lively sports an ethnic-inspired tunic top in a demure pattern with cuffed short-shorts and gold loafers for laid-back preppy-girl perfection (adorable pooch optional.)
This Tory Burch Stephanie tunic in navy yves ($295) is the ultimate in uptown-inspired casual chic for day or night. Its graphic chain pattern is embellished with a sprinkling of metallic pailettes for some extra dazzle, while the 100-percent cotton material and rounded Mandarin collar keep it comfy.
The adorable grosgrain ribbon belt is back in New York & Company's linen-cotton shorts ($19.95) These short-shorts know how to be flirty and fun while still being ladylike.
Want a cheery summer shoe that you’ll wear to death? Kate Spade's Dandy loafers ($156.45) fits the bill and then some. The flashy metallic gold hue will satisfy your need to shine while the moccasin-inspired whip-stitching faithfully recalls a footwear classic without being too Minnetonka.
The tomboy look is vintage prep, but AnnaLynne McCord shows how easy it is to turn up the girl-quotient on this short, belted shirtdress by adding a newsboy cap, skinny scarf, white sandals—and a lot of leg. Now, that’s grocery shopping done right!
The beauty of Victoria's Secret's belted linen shirtdress ($78) is that from the minute you put it on, it will feel as if you’ve had it for years and it's worn in exactly the way you like. The front flap pockets give it a little extra tailoring while keeping the look easy 'n' breezy enough for a day at the beach.
American Apparel's shirtdress ($60) looks like the Oxford button-down you stole out of your boyfriend’s closet—only better. It can be worn three ways: as a belted shirtdress, a tent dress (sans belt) or a straight-up dress (belted from behind). Roll up the sleeves or keep 'em straight for added versatility.
The Gap's classic striped shirtdress (on sale for $44.99) gets the preppy boy-meets-girl styling just right. This piece gives you all the comfort of an easy button-down with the sweet, flirty flourish of the roll-up ties, making it perfect for the dog days of summer.
Click here for our Romantic Boho gallery.