I am happy to announce that we have a winner in the OTC TRUE PREP Swag Bag Giveaway!

Jack A. Mallon (#26) and his dad’s patched tweed blazer, ancient history class, squash racket and professorially demeanor added up to a winning combination.  I cannot tell you how hard it was to select a story that best reflected what being “preppy” is really all about and also told us all a little bit about the writer.  From seersucker at the Kennedy Center to matching Gold Cup outfits, prep schools to winning the right to not wear socks with loafers at the office, every one was a great read.

I will always laugh at the Georgetown bow tie “you’re-stealing-my-thunder” incident as well as the touching reminiscence of watching Sargent Shriver and his grandson in church, dapper and gentlemanly even in mourning for his late wife.

Other great lines include a friend noting that the “Dress code at Yale is apparently Andy Bernard style”; “Yep, my initials are BMOC”; and Andrew Y’s entire story of his big prep moment running into the realty that is old school prep plainness.

Thanks again to all who offered up their stories and please be assured that I read and re-read every one.  Each of you touched on the many aspects that mark the genuine nature of preppy culture.  From deprecating self awareness to duct-taped boat shoes, every one is it’s own cultural observation.

Here is the winning entry:

I’m a second year history student at the University of Guelph and last week, seeing as it was the first week of classes, I wanted to make a good impression. Dawning my father’s tweed blazer from his days at Guelph with the University crest and elbow patches, as well as khakis, a blue oxford, and a rep tie I set off for campus, bringing my squash racquet with me for a game later that day.

Upon reaching my Ancient History class about ten minutes late I strolled in, hoping not to interrupt my professor. As fate would have it I had been taught Latin by the professor several times, and when he saw me, halted his lecture and greeted me in Latin and started telling me how squash was his favorite sport and that he’d like to play me sometime. Glad to have avoided making a bad impression with my tardiness I took a seat for the remainder of the lecture. After class as I was walking down the hall I was approached by three or four students asking me a multitude of questions about the course.

It turned out that my friendliness with the professor and my overall appearance had led them to believe that I was the assistant professor. I played along and answered as many questions as possible. People can say what they wish about preppy attire, but for me it is the embodiment of dressing for success.