Hip, and the Art of Cool

Something struck my mind the other day while walking through Central Square - the difference between cool in Toronto and cool in Boston. Now both towns have their fair share of hipsters, renegades and wannabees, and yet there is a clear difference. And I think it all comes down to effort.

Cool in Boston is artsy, edgy, rejection-of-the-mainstream cool. Labels (except retro band shirts) are rejected for clothing. But your threads must be cutting edge (fresh from H&M - no label there), or just-saved-from-the-garbage-dump retro. The weirder the band you know/follow, the cooler you are. You gotta live in some urban-student ghettoesque place like Brighton, Allston, Southie, Somerville or Central Cambridge (and only Central if you MUST live in Cambridge). Odd understanding of the locals and misfits is a plus.

But all of this knowledge, clothing hunting and gathering, and urban scoping can take a lot out of a person which relates to my point about effort. It takes a tremendous effort to be so damn cutting edge here.

Yet for all their hipster cool, the kids are desperately holding on to a secret - the effort they put in is a rejection of their upbringing. Because for all the poverty, ghettoisms and urban streetwear chic, they are in fact a bunch of upper middle class kids who grew up in the 'burbs, in respectable houses with parents who were prone to putting letters behind their names for professional purposes (PhD, MD, etc).

The cool kids of Boston don't live in real poverty, they don't live in the real ghetto and they can have their cake and eat it too. Its all pretty fake and contrived really. Cool as conformity - a very specific sort of genre. Cool seperates you from the townies, the sports fans, the JCrew kids and the old money.

Now in Toronto you're going to find that same group of people - the suburban kids who grew up on a strict diet of mowing the lawn on Saturday, cruising the mall regularly and dreams of wheels to get them around the vast sprawl of the GTA. But (and here's the point) people in Toronto aren't trying that hard to be cool as grown ups.

For one thing, the whole "poverty is liberty" mantra is dead in the water. The cool ones in Toronto want money. They want exotic vacations to Namibia, Southern India or Brazil (to buy them some cred with their doctor, accountant or taxi cab driver from one of those places). They want the cool stuff you can only buy at the high-end urban chic shops on Queen and in Yorkville (because Linda Reeves or Marilyn Dennis might drop by). They want the condo on King or College. Failing that they want the apartment at Yonge and Eglington, at the very least. They want to eat out at the top tier restaurants. They want this stuff, and aren't afraid to tell you about it.

In Toronto weird bands are the mainstream (everyone knows to hang at the Drake on Friday night - you never know when members of Broken Social Scene might show up), clothing is supposed to look chic and high end (otherwise Holt's would have been out of business centuries ago) and having the ability to brag about seasons tickets to the Leafs matters way more than the weird neighbours you got next door or the homeless guy who will sing for your dollar.

Toronto is cool because you don't have to try so hard. The wonderful thing about loving diversity (and we do tend to presuppose this relates only to ethnicity) is that everyone is given equal opportunity to be cool for 3.5 million very different, very unique reasons. Cool doesn't mean conformity - it means individuality.

Cool? In Boston you do have to try. In Toronto you already are.