I'll be honest- it would be a bit weird if he bought me clothes on a regular basis. One reason- I tend to like to take care of myself, I'm very independent and would hate feeling like a kept woman. And as great as my guy is, I honestly wouldn't trust him to buy me clothes by himself. Growing up with brothers, I know that most men haven't a clue about sizes for women (they don't make a lot of sense, so it's not really the guys' fault), and since women tend to all have their own unique style I'd say it'd be nearly impossible for any guy to pick out what his girlfriend might like, and certainly it would be for my boyfriend.
If I were with him, it would just be uncomfortable for me, it would feel like I was telling him to buy me things which is so not me- I pay my own way.
The exception to this is the occasional gift of PJ's or lingerie- those I'm comfortable with him buying. PJ's because, well, I don't wear them out of the house and they don't have to fit perfectly anyway. Lingerie, obviously lingerie from my boyfriend has its sex appeal on both sides- he's thinking of me wearing it, when he buys it, gets to please himself when I actually wear it, and I'll feel sexy wearing it (around him or not) because he chose it.
But as for day-to-day clothes, nope sorry, it's something my boyfriend can't buy for me. Kind of like he can't buy my hair products or skin cream- it's just something I need to buy for myself. Of course, I don't like my boyfriend buying me things on a regular basis anyway, unless we take turns, so this is rarely an issue for us.