The Dressing Room: the preppy handbook


Not too long ago, I flew to Boston for a short getaway. Aside from the boisterous sea of yellow and black that swept over the city during the Bruins rolling rally, Boston — or more precisely, Bostonian dress — was essentially exactly as I remember it from my first visit there as a kid in the 80s: country club chic.

An island hopper away from the clam bakes and whale-printed clam diggers of Martha’s Vineyard and Nantucket, Boston is a beacon of New England preppy. I worked a summer as a nanny in Nantucket before my post-grad and experienced first hand (sticky from candy-smeared toddler faces though that hand may have been) grand 4th of July parties and yachting trips with vacationing New York CEOs and Upper East Side ladies-who-lunch. Overarching observations: Nantucket Reds (otherwise known as pink pants to everyone off the island) are not flattering on any man; oversized pearl earrings may outlive the cockroach in the East Coast and at least 90 per cent of Lilly Pulitzer's profits must come from this region.

With brands like Bass resurfacing, top siders refusing to be pushed to the back corner of the closet and S/S 2011 runway shows (including Canada’s Dsquared2) recalling the time tested traditions of Polo Ralph Lauren, style trends are skewing all-American this summer.

While I did once eagerly await family road trips to Boston as a kid (solely because of our stop in Freeport, admittedly, home to Bass, Ralph Lauren and Abercrombie & Fitch outlets), now, out of the 80s and well over falling for a guy in a popped collar and chinos, I’m less than 100 percent on board with the preppy comeback. There are, though, some gems in the current throwback collections, as I discovered over that weekend in Boston.

Never would I imagine that dinner at a crab shack on Boston’s Long Wharf would demand the degree of contemplation I found myself giving to attire. But, for whatever reason, the party I was traveling with (my enthusiastic aunt and uncle, visiting from Taiwan) were intent on going native while in New England, and that apparently meant yards of khaki were in order. I suspect they came to this decision based on the combination of watching The Nanny Diaries prior to coming to Boston, and visiting the John F. Kennedy Hyannis Museum upon arrival.

Now out of the 80s, and well over falling for a guy in a popped collar and chinos, I’m less than 100 percent on board with the preppy comeback.

Convinced that crab shack dress code required a sweater around one’s neck and some form of linen garment, be it a white button up or an off-white short, they usher me to the nearest J.Crew — a store they know by reputation alone. It doesn't disappoint them. Within 20 minutes, I find myself in a small dressing room facing hanger upon hanger of twinsets and cotton chambray items hand-selected by my aunt. Finding my way into a Bermuda jacket, I'm certain that this process of assimilation is going to be painful, and then, as if struck by a sudden bout of Stockholm syndrome, I look in the mirror and find myself liking the pair of ikat board shorts I'm wearing. Is this coastal preppy? And if yes, how could one not like it? And the paper-thin feather knit henley — could it be the most comfortable top a person can wear? Then there is J. Crew’s extensive collection of Breton stripes to choose from. A staple closet item for the preppy and hipster alike, the brand has versions enough in store to satisfy both style sensibilities. Whether looking to nod at one’s maritime surroundings as per a visiting uptown elite or play up your artist persona a la Andy Warhol, the “swingtime” sweater is a multi-purpose silk and linen (yes linen) wonder.

Standing before the mirror in the black and white stripe blouson dress (pictured above) from J. Crew’s current collection, with its spaghetti straps and elastic waist, bringing preppy back wasn’t looking so bad. I could happily wear this dress — even with a cotton and linen blend cardigan around my neck (only at the crab shack). Taking a browse around the shop for myself reveals the in-store collection’s versatility (i.e. not just for professional twenty-somethings looking to trade up), and makes it clear to this preppy reject why fashion insiders have their eye on J.Crew Inc.’s in-house tastemaker Jenna Lyons, creative director and president. Aside from the obvious factor of her of White House credentials (First Lady Michelle Obama is a fan), the visionary and au courant Lyons has been revitalizing the brand — careful never to lose sight of classic sweater sets and chinos — since 2007, after working her way up from senior vice president of women’s Design to creative director.

A fresh J.Crew convert, I’m counting the sailboats on the Humber Bay until August, when the company will open its first international location in Toronto’s Yorkdale Shopping Centre (women’s clothing and accessories only, unfortunately, for local wavy-haired gents looking for a nice ribbon belt to go with their rope bracelet). Until then, I will bide time flipping through the brand’s catalog and pouring over Jenna’s Picks online at, when not watching Pretty in Pink of course (Steff’s shoulder pads seem to get bigger and bigger each time I watch).

Toronto-based writer Jennifer Lee is the editorial director of FILLER magazine, an online fashion and culture journal. She is also the co-editor of Hardly magazine, an arts-centric online teen publication for Canadian girls. Her column, The Dressing Room, appears weekly.

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