For the shirts I'd rather not do something complicated like a contest.
I think the best and most satisfying solution for everyone will be to
make a shirt that is as simple as possible and emphasize WordPress
(the thing we all actually care about) rather than WCMTL.
COLOR: I hate to be a fascist but I really don't want black shirts. We
all know black is the official color of nerds, but I know I already
have too many black shirts from events like this. My personal
preference would be sky blue like the site is. That said I understand
that some people are particularly uncomfortable with light blue. SO:
These days I love charcoal/dark grey colored shirts. They are dark and
similar to black but just 'colorful' enough that they won't make us
into invisible ninjas. I'm not sure what kind of shirts we'll be using
but American Apparell has a great shade of charcoal. That's what I use
in the attatched mockups. NOTE: We almost definitely want to keep it
to just 1 color of print. Adding colors adds cost really quickly, and
IMHO 1 should be enough :)
DESIGN: IMHO the shirt should mostly be a WP logo in the center of the
chest. It's classy, easily recognizable and it makes you feel like
Iron Man but powered by PHP instead of magic nuclear energy. The
attached mockups show what I mean. While I'm tempted to just leave it
there and give people WordPress shirts (anyone else think this is a
good idea? I don't really care about promoting WCMTL as much as having
nice shirts) we should probably include something that indicates
Montreal and Wordcamp. The three mockups show three versions of the
logo with a bit of text.
Personally I love the way it looks to just have the logo and
"Montreal 2009", which to me reads as 'WordPress Montreal 2009'. That
said I think Logo + "WordCamp Montreal '09" also works really well and
will make a lot more sense to people who don't know/recognize the
WordPress logo. The last design has the words 'WordCamp montreal '09'
at the bottom on the side. This is a fairly stylish trend these days
for keeping the main part of the shirt clean. I'm not totally sold on
it though and I'm pretty sure it will cost more to do it that way
because we'd be printing twice instead of once.