For T.O., try to get yourself age verified before departing. This will allow you to look through the goods of some retailers online (who may not necessarily be brick & mortar) before committing to an appointment and/or visit.
and peruse wares there. Great guy to deal with in person.
For good surplus, try Army Issue in Port Credit (ensuring you get a burrito from Burrito Boyz next door), Army Outfitters in T.O. or Creative Outdoors in Richmond Hill.