Daddy and Mummy are helping you pack their ancient Rover full of your L.L. Bean duffel bags and Granddad’s old steamer trunk from his Deerfield days. Yes, it’s time for the annual trek east to boarding school. Oh? You graduated eons ago? Well, whether you matriculated at Ethel Walker or Andover (or want to look like you were), here’s everything you need to sport that rarefied style in whatever ivy-covered halls you call home.
Surely you remember
The Official Preppy Handbook, the 1980s mega-seller that was required reading for the private-school set? Oh, that’s right … you weren’t born in the ’80s. Catch up with the sequel,
True Prep (Knopf, September 2010, $19.95), penned by the preppy original author herself, Lisa Birnbach, with Chip Kidd. They’ve rewritten the annals of prepdom,21st-century style.
Whether you’re wearing a pleated skirt or flat-front khakis and a blazer every day, when there’s a chill in the air it’s time to pull out The North Face fleece jackets. We’re partial to the TKA 100 Glacier quarter-zip fleece. $50, at Nordstrom, REI, The Sports Authority, Sun & Ski Sports, Urban Outfitters, Whole Earth Provision Co.; thenorthface.com.
Back when your parents met at Choate Rosemary Hall, no one got through a slushy New England spring without hideous (yet somehow cool) rubber-soled, heather-topped Bean boots. Now Hunter Wellie boots are de rigueur prep-school attire. Hunter’s Carnaby Boa boots in black give Muffy a fashionable edge. $225, at Neiman Marcus, Stanley Korshak; hunter-boot.com.
Talk about old school. These Tretorn Nylite women’s sneakers haven’t changed a stitch in decades. Land’s End Canvashas now revived the first luxury sports shoe ever made. $55, at landsend.com/canvas.
L.L. Bean is making the classics a little more modern in its new catalog/Web site, L.L. Bean Signature. Our fave: his Saltwash pullover made of every prep’s favorite: 100 percent cotton — salt-washed for maximum comfort, no less. $59, at llbeansignature.com.
Nothing whispers trust fund like a classic Cartier Tank with alligator strap ($7,850, at Cartier). On days when you want to downplay it, though, switch to a Toy Watch (from $195, at Saks Fifth Avenue; toywatchusa.com), and no one will know how much you’ve banked. Isn’t that really the point?
Jack Spade channels the sailing vibe with this navy awning-stripe messenger bag ($195), with room for your iPad. At jackspade.com.
Talk about taking it personally. The Queen of Cashmere weaves your initials boldly onto the sleeve of these crewneck sweaters made of soft Scottish cashmere. The fetching diamond-shaped monogram sets you apart from the machine-monogrammed crowd. $625, by special order at saksfifthavenue.com.
Since you’ve hauled Tide to do your own laundry, don’t chance it with Hamilton’s custom shirts. Pack your weekend duffel with a few classic long-sleeve navy gingham shirts made with Italian double-ply fabric. The prewashed, spread-collar button-downs even have a retro slot for your pen on the chest pocket. $185 each, at Barneys New York, Pockets Menswear, Stanley Korshak; hamilton1883.com.
Rhonda Byrne (who wrote the New Age book
The Secret that your stepmother is always quoting) would encourage you to envision yourself walking through the ivy-covered square of Harvard Yard. Maybe wearing crimson “Veritas” emblazoned on the Harvard tie around your neck will assure you’ll get there, too. Vineyard Vines ivy ties $75 each, at vineyardvines.com.
Provider of your uniform Sperry Top-Sider Chukkas (replacing Bean’s Blucher Mocs), J.Crew custom-colors their unisex version, natch ($125). They’ve also secured Belstaff’s Roadmaster jacket in waxed cotton ($695). This British fave is the very definition of rugged cool. At J.Crew; jcrew.com.
Remember those drafty dorm rooms at Exeter? Keep the chill at bay with L.L. Bean’s striped-ticking flannel sheets. Flat or fitted $25 each, at llbean.com.
While mother wore Pappagallo, our generation sports politically
correct, unisex espadrilles by Toms Shoes — the charity brand that
donates shoes to a child in need with every pair purchased. From $44, at
Cotton Island, Nordstrom, Stanley Korshak; toms.com.
Dressing down on the weekends? Nothing beats a classic. Levi’s are the jeans for guys who aren’t trying too hard. (Not to mention, the savvy girls who raid the boy’s department and sport his.) At levis.com.
When the houseparent calls “Lights out,” dress down in Claridge + King’s cool menswear-inspired pajama pants and boxer sets made with cozy cotton shirting. Not like you’re trying or anything … $62 each, at claridgeandking.com.
Don’t head off to Avon Old Farms or Madeira without your trusty rain gear. Hadleigh’s bespoke umbrella takes it up a notch. Select the fabric, leather handle and dimensions of your custom parapluie, and engrave that little silver plate at its base with your initials. At Hadleigh’s, 214.770.4743; hadleighsbespoke.com.