Tiffany does sell watches at its stores on Bloor and at Yorkdale. Also, you might want to call the Gucci store on Bloor to see if they have the watch that was mentioned here (though I believe that Holt's also sells Gucci watches). And I am a very happy owner of the Cartier La Dona; they also have their boutique on Bloor, even if you want to go in and browse with no intention of buying. They are very nice and you would at least have an idea of style.
Also consider some of the double wrap (officially called double tour) watches by Hermes. They are really pretty.
And ... if you don't want to spend a ton but want a look to try out, don't overlook Swatch. I have had several Swatch watches and got a ton of compliments on them and they look great. Also Michael Kors for something more fashion forward without breaking the bank. I think they are stainless and not nickel.
Thanks! Hopefully I can stop in Toronto on the way home Saturday. I will probably hit up the yorkville area since I know it better. I have nickle allergies so I guess that is another thing I have to think about too when I am looking.
I don't remember seeing Gucci at Holt's guess I didn't look hard enough last time!!