I don’t like the new Tea Partay video for its genius as a work of viral marketing (over 700,000 downloads on YouTube). I don’t like it because it mimicks the format and rhythmic structure of hiphop videos. I like it because I’m an unashamed preppy.

I don’t mean I jumped on the casual Friday bandwagon in 2000 and never got off. I’m not talking about stain-resistant casual chinos. I’m talking four pairs of penny loafers. With six resoles among them.

Twenty years ago this month, I was strolling the aisles of Halperns, the small chain responsible for forcing young men and women across Canada into grey polyester-blend slacks, white shirts blue blazers with brass buttons and plaid ties. The outfitter for Canada’s boarding schools. (long story there)

Wearing dress pants, button-downs, golf shirts and dress shoes to school was not a stretch. I had spent the previous years posing around downtown Ottawa as a mod. Making the transition to boarding school was not a great conceptual leap – even if it meant a radical shift in the implied socio-economic values of my new clique’s uniform.

In fact, the popularity of “transition” icons like Rick Astley (YouTube), the Style Council and Sloan Rangers meant preppy style was culturally acceptable outside of Princeton, Greenwich and New Haven.

Preppy style had been mocked by the Official Preppy Handbook and then, ironically, taken off in popularity. By the time I arrived at the party, Ralph had been throwing up stores as fast as he could. Youth brands like Club Monaco were drafting behind with lines of white cotton shirts, similar styles of chinos and v-necks. (And the “CM” logo meant they were already monogrammed!

Twenty years later, I still head towards the chinos, pinpoint cotton and plaid when shopping. Argyle is my friend – in moderation. And real men don’t do flourescents or reflective material – unless its on boating clothes.

By the way – I’ve never played golf, and I don’t belong to a country club. And while I may never have played a lawyer on TV, I do admire the work of 300 pound Samoan attorneys.