Hey everyone, thanks for all your advice and opinions.
I think I'm getting closer to finding 'that' bike. =)

I mostly ride around my city just for kicks, to run errands, and because it beats driving/ finding parking, but I don't want to exclude the option of biking on somewhat rugged paths/backroads.
In any case, extreme's not my game. I can't even pull a bunny-hop.

As for my budget, I'm hoping to stay in the $400-$700 range, but I'll spend more if it's necessary to get a stylish bike I'll get a lot of use from.
The Cross Check certainly describes the kind of bike I'm looking for. I'll keep it in mind.

I'm definitely not crazy about coaster brakes. I know not all those bikes in the links are quite what I'm looking for, but I was hoping someone might have an idea when looking at them what a good alternative would be.
Boo-Hoo. Why is it always so hard to find things for my size. (I swear, clothing manufacturers hate people with 33x33 measurements!)

I did check out a few bikes at a local bike shop, but the fella there told me that they didn't carry anything quite like what I was looking for. He said the hybrids wouldn't be good, even though what I read about them online suggested they could be used for city and slightly rough terrain.
They had one cruiser, but it was a single-speed with pedal brakes.

I took a look at some electra bikes online and they do have some pretty nice lookers.

I like the Super Deluxe Cruiser, but it's only got 3 speeds.

Some of the Ticino bikes are interesting, but I don't know that I'd ever need a 2o speed bike. (My current bike is 18-speed but I only ever use 8 of them.)

I really like the functionality of the The Royal Amsterdam. The style is something I could get used to, but as long as it could handle the sort of use I'd give it, it seems like a pretty good bike. Does anybody have experience with that bike, or any thoughts on it?