I've come to the conclusion that, for the upcoming year, and perhaps beyond, my teaching-attire is going to be strictly jeans-and-sneakers. (I like the stuff Dave Chappelle wore while hosting his show; perhaps my shirts won't be as loud, but that's the basic idea.)
In my previous four-year teaching stint, I'd usually wear a button-down shirt and khakis — no ties, except on Hallowe'en when I'd dress up "like a teacher" — and occasionally, maybe once a week, wear jeans and sneakers. On the days that I did, I felt lighter and bouncier and friendlier; when you're dealing with upwards of 70 ridiculous teenagers a day, that's a good mood in which to be, I've found.
When I supply-taught this past May and June, I dressed-down every day, and it didn't even feel like going to "work," really. (Mind you, being a supply-teacher with no lesson-planning and no marking leaves you with a substantially easier job, with much shorter hours, than a regular, daily-grind type of gig. Still, though, it felt nice.)
Now, contrast this with the other side of my life lately: being a grad student at Queen's. I indulged in your standard student-type behaviour that I largely missed at UW (it helps being around undergraduates), and really enjoyed my time there, recent thesis-related fiascos notwithstanding. As such, I've had a page on the ubiquitous Facebook for about a year; for those not familiar with it, it's a social-networking site, showing who knows who, and from where, and what you're doing this summer, and what bands you like, and so on. (Hey, c'mon, everyone I knew was doing it, too.)
That website has encouraged the mixture of my teacher-life and my student-life: I have ex-students of mine (who are now university students themselves) listed as acquaintances on Facebook, and vice-versa. This is a confluence that, I imagine, not too many educators experience; they teach their kids, their kids go away, and they never see them again. It's a shame, though, because some of these kids are really interesting people, and will turn out to be great adults.
In small towns such as the one in which I grew up, it's a lot more commonplace to run into your old teachers (or, in my case, have one as your aunt). In cities, with people to'ing-and-fro'ing all over the place, it's less so; I live in midtown Toronto but work in Scarborough, and there are several hundred thousand people living between those two places. As such, the demarcation between professional and personal life is very clear, both metaphorically and geograpically.
...which brings me back to jeans-and-sneakers: it's the attire in which I feel most like myself. It's a lot of work, having two personae — Teacher-J and Regular-J, if you will — and, after having given both of them a whirl in the classroom, I feel like the kids respond better to the latter. (After all, Teacher-J is just an answer-box with legs and arms, and Regular-J is a person. Since real learning doesn't take place without a trusting relationship, and relationships are between people, which do you think works best?) So, if Levi Strauss and Hank Adidas make me feel more like me, and that's good for the kids, why not ditch the khakis?