Wow! The ignorant people answering here... really nothing gay about wearing girls clothes or all women would be gay since sooner or later them wear mens clothes. Gay guys don't wear skirts. Clothing doesn't make you gay! (Something that sexually insecure and homophobic men believe).
It would seem he has discovered some girls clothes ARE practical and feel good and that is something most guys haven't explored or they would understand. Really no problem with this as it is his "style".
leading clothing designers have stated all clothing is unisex except for the bra and jockstrap (the only two pieces of clothing that are sex specific). Anyone can wear them. Many guys like the fit of tight girls stretch jeans and those were popular in the 60's for men so it is a returning fashion and if you stop to think about why would anyone have a problem with a guy in a skirt? A skirt makes far more sense for the male anatomy than for a female since there are no crotch seams and the freedom of movement is incredible for a short skirt but most guys don't know that! (Men have worn skirts far longer than women throughout time and many were micro mini length. A regular mini skirt IS the same length as men's gym shorts at about 12 to 14" long.
So yeah, as long as he isn't "cross dressing" trying to look like a women (a fail every time) then what's the problem? If he wants a bra then he has mental issues as that makes absolutely no sense.
See these guys in skirts and note they still look like guys just as women in pants still look like women: http://www.picturetrail.com/sfx/album/vi... They are obviously NOT "cross dressing" trying to look like women.
There are a number of commercial services that'll provide that function for you. Among them: CafePress, VistaPrint, and Zazzle. Not an endorsement, but I've used Zazzle for that purpose, uploading artwork and photographs. And I've made some money from it.
To oversimply copyright law, once you "publish" an item, you've copyrighted it...unless the item is in the public domain (such as a picture by Michelangelo)--in which case you never owned the copyright to begin with. When you upload a design to one of those services. On sites that provide a "store" to sell your product--such as CafePress and Zazzle--you're giving those services a limited right to reproduce your design for your benefit.
Your original creations--pictures and logos, for instance--already are legally yours. You're actually protecting that intellectual property by publishing them.
Incidentally, the services I've mentioned are print-on-demand. So, at least for the basic service, it doesn't cost anything up front. You upload your designs, price them, and offer them for sale. Generally, there's a base price for each item--t-shirt, hoodie, etc.--and anything above that base price is yours. So if the base price for a t-shirt is $15 and you price yours at $20, you make $5.
Again, I'm not endorsing any of them, and there are a bunch (beyond those I've mentioned) to choose from. But that's what I'd do if I were in your position.
Hope that helps.