I'd tell you to look at some place like American Eagle, Rue 21, H&M, or Urban Outfitters since they tend to carry smaller sizes for men, but I dunno if you can really pick or choose where you go right now.
However, all of those stores also carry female clothing, so if you're still planning on being secretive about purchasing men's clothing, then those places would not be a bad place to start. However, if you are not binding yet, a nice baggy shirt could be a friend to you. However, if you are really thin around the stomach & waist area, you will have trouble finding men's pants that fit you in your regular ol' department store. I can get away with a 28 or 29 waist if I belt it, but sometimes stores won't carry anything lower than a 30. Even with a 28 or 29, I literally mean that I can get away with it - but it isn't desirable. I usually can wear a 26 waist without having to belt. Depending on your style, you'll probably be able to find jeans that will fit you at Hot Topic or American Eagle. Even though HT is awful nowadays, their jeans are usually labelled as more of a unisex item from my experience. There are nicer jeans out there, but I think you can find waists measurements as small as 24 there. I don't wear my pants that tight anymore, especially because of my packer and because it usually emphasizes your hips, but yeah. I still think it would be helpful if you told us where you are planning on going, because you may be disappointed at certain stores. If your midsection is build anywhere near like mine is, you may end up seeing a lot of shirts you like, but won't fit you (medium is sometimes the smallest size they carry in most of their shirts and or their both waist x inseam measurements of pants will end up making you wish you were taller). I dunno, you could always shop the boys department, but it's kind of questionable as to why you may be buying boys clothes "for a friend". Also, I've always found it to be awkward when I end up owning the same exact shirt same shirt as some who is potentially over ten years my minor. >_< I don't know if that would bother you, but you might want to take that into consideration.
As for
Kyle_S, have you ever heard of
www.topman.com?
They can be rather pricey at times, but the quality of the clothes is worth it. They also sell button up shirts for men (not boys) from XXS-XXL. I do own some men's small button ups, but I'm maybe 5'2" or something like that, so they can be a little long at times. I've always been more comfortable wearing an XS men's button up, but alas, there are only certain places you can find them. American Eagle, as I mentioned earlier, sells smaller men's clothing as well. They also carry XS button up shirts. Oh, and Urban Outfitters does sometimes as well.
:]
