Thats a lot! If you don't want to ask him what size he wears or you cant sneak and look in his closet then pay close attention to the models of the stores you may shop. For example, if he is a thicker guy, stay away from stores like Hollister or Ambercrombie because their clothes are targeted to thinner body types. Also, clothes are cut so different now a days, so if you buy something with a particular fit just ask an employee what kind of fit it is. For example, Express has 3 different fits for men in their pants: Agent, Photographer, and Producer. Agent being more loose fitting, Producer fitting a little loose but not too tight, and Photographer being more of a slim fit. So again, know his physique! Trend??? Make sure you incorporate his style into what you buy so that he doesn't get offended and think that you are trying to "change" him. Don't venture too far off his style because most men wont tell you they don't like it they just won't wear it. Clothing shops??? Depends on what you want to spend and his size, but just to get a glimpse of everything I would try a department store first. Why? Because it is a good gesture, not really sure. I LOVE to shop and style and fashion is everything to be so I shop for my man because I get to express myself through his clothes too and it gives me more reason to shop. When I go shopping, I literally have to sneak my bags in the house but if I grab him a thing or two, I can divert his attention from my bags!!! LOL, sad but true.