There is a lot of accessory stores in Calgary (i.e. Watch Out, Spareparts, Eye Appeal, etc) that are devoted to things like watches and sunglasses that will carry a lot of variety in terms of names and different prices.
Lots of dept stores carry watches, and so will some clothing stores like Guess. Skate shops actually carry some pretty cool and funky watches by brands like Nixon and the like. Just cruise Inglewood, Kensington, 17th Ave, 11th Ave and 4th st and pop into the different stores to see if they have anything that you are looking for... that's what I would do.
You should probably pick based on both function and style that you are going for. For instance, I currently wear a Citizen Eco Drive everyday and am very happy with it, but it isn't well suited for the outdoors or underwater use.
FYI - Storm watches are probably my favorite brand. They are really, really cool and unique watches. I don't own one, but I have always admired them. Check out
www.stormwatches.com . Also, I am pretty sure that Watch Out on 17th carries them if you want to see them in person.