Rethink Breast Cancer's Rock the Preppy fundraiser recalled the era of alligator logos, schoolgirl knee socks, and rolled-up seersucker pants. The Gatsbyesque affair unfolded at Brassaii, a fashionable restaurant on King Street West, which the organizers dubbed The Estate. Amanda Blakley, Rethink's national manager of special events, said "we chose the preppy theme because we aim for something hot and trendy each year, and we had noticed a resurgence of the preppy look of late." The approximately 750 guests played along, sporting logos like Lacoste, Polo, and Tretorn and looking, for the most part, clean cut, buttoned down and tucked in. The successful event raised $100,000 for young people affected by breast cancer.For the benefit of potential guests unfamiliar with a style that spent the past two decades in the fashion wilderness, Mighty Digital Direct, a division of ad agency Bensimon Byrne, created an interactive website with tips on dressing conservative yet chic. The site also offered lessons in proper preppy parlance. These translations of upper-crusty, 1980's lingo into everyday English appeared at the event as decor—on posters, signage, and even table coasters. Indoor activities included underwear consultations by Mura Image Consultants and skin assessments by Dermalogica. Schwarzkopf administered ponytail hairdos, and there was a silent auction for items such as a gift certificate for Ki restaurant and cooking classes for two at Dish Studio.
Outside on the large patio, guests played preppy sports like horseshoes and eyed a group of Argentinian professional polo players from Polo Management Services, who straddled wooden ponies and demonstrated their swings. Absolute Tent Rental supplied tenting for V.I.P. space, which featured fake grass and country-club-style patio furniture. Indie band Uncut, performing on a stage with pink up-lights, had the crowd dancing and shaking their ponytails into the morning hours.
Outside on the large patio, guests played preppy sports like horseshoes and eyed a group of Argentinian professional polo players from Polo Management Services, who straddled wooden ponies and demonstrated their swings. Absolute Tent Rental supplied tenting for V.I.P. space, which featured fake grass and country-club-style patio furniture. Indie band Uncut, performing on a stage with pink up-lights, had the crowd dancing and shaking their ponytails into the morning hours.

Professional Argentinean polo players posed by a wooden horse at Brassaii for Rethink Breast Cancer's Rock the Preppy fund-raiser.

Posters from Bensimon Byrne offered tips on proper preppy dress and parlance.

The outdoor V.I.P. space featured fake grass and country-club-style patio furniture.

A video screen at the entrance promoted the event and showed clips from preppy movies like Pretty Woman.

Guests could get facials at the Dermalogica skin bar.

Professional hair stylists from Schwarzkopf offered ponytail hairdos.

Indie band Uncut performed on a stage with pink up-lights.