My guy and I are going shopping together for the first time this Sunday. I found out which is not a surprise that he doesn't like shopping. The part he likes about it is getting new clothes at the end and spending time with me :) I kind of know his sizes so if I ever did want to buy something for him, I could.
Yes, I do like to go shopping with my girl. It's a day out with her and I get to see her try things on. We usually stop at an underwear store while we're out, which I enjoy since I'll be seeing it later that night. But I just like clothes shopping in general. I don't know if I could be considered an anomaly, but I pay attention to fashion probably more than she does and I make sure she doesn't pick anything ugly. But if your guy doesn't like shopping and you plan on bringing him along someday, make a fun date out of it or he'll secretly hate you for the day.
I hate shopping, mostly the waste of time it is. When I go to shop for my own things it takes me like 20 minutes and I have enough clothes for the next two years. When I go with my wife it takes like two years to have enough for the next 20 minutes...
Shopping for her clothes is a bit easier. I take my tablet or laptop and just sit somewhere and work :D