Here’s the thing: even at the height of my all-black-wearing, semi-goth teenage ’80s youth I still had a soft spot for all things preppy. I had dabbled in the preppy look in seventh and eighth grade, wearing Ralph Lauren logoed-polo shirts and sweaters, hairbands, argyle and plenty of madras plaid. I read Lisa Birnbach’s The Official Preppy Handbook more than once without understanding it was satire. Rather, it was an actual guide for me and my friends.

I subscribed to the L.L. Bean catalogue and cursed the fact that Sporto duck shoes and Sperry Top-Siders were too wide for my unusually narrow feet and therefore unwearable.

By the time ninth grade hit I had abandoned preppy and was fully immersed in a black-clad, Bauhaus-listening, hate-the-world phase that would last for several years. Still, I couldn’t help but secretly admire preppiness and all the fashion that went with it, and that had a lot to do with my first visit to some of the New England States when I was fifteen.

We flew to Montreal and drove through New York State, Vermont, New Hampshire. The whole point of the trip was so my dad — who was very much into his thoroughbred breeding and investment hobby at the time — could go to Saratoga Springs during peak racing season in August.

While I had always been around rather conservatively-dressed types having grown up in the clean-and-pristine Canadian suburbs, I had never seen with my own eyes full-blown, east coast preppies — ones who looked and talked exactly like the people in Lisa Birnbach’s book. It was at once exciting and terrifying.

That real, true-blue-blood preppies actually existed and were right there in front of me, talking to my dad, gave me an unexpected thrill and I remember clocking all their looks and labels carefully. Then I remember being horrified with myself for being so impressed. I was not a preppy. I was alternative. I was other.

It was hard to resist reverting back to my old preppy ways that summer when back-to-school shopping. I did break down and buy an oversize Perry Ellis sweater with a vaguely fair isle-ish design. But I told myself that was okay because it was black-and-white.

Images:

1. Thomas Hooper for Seventeen, October 1983.

2. Paolo Roversi for Mademoiselle, September 1984. Clothing by Perry Ellis.

3. J.G. Hook, Elle, February 1988.

4. The Gap, Vogue, November 1986.

5. Gucci, Vogue, June 1984.

6. Bench, Elle, September 1987.

7. Rudy Molacek for Glamour, September 1982.

8. Keds, Elle, September 1987.

9. Ralph Lauren, Harper’s Bazaar, March 1982.

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