OK, I really am hesitating to post this, but it's been on my mind heavily for the past couple of days so here goes...

I have been dating a girl for a couple of months now, and she is truly beautiful and we get along great. She constantly compliments me and I of course do the same. I am a basic t-shirts and jeans-girl type of guy. There were times in the beginning where she would dress up to try to turn me on, and I would almost pass out because she looks so hot. But lately she has been wearing other types of clothing, stuff that really doesn't look too flattering on her and wouldn't look particularly great on anybody in my opinion. Some of her shirts look like....well....maternity shirts. She thinks she looks cute in them, but I don't have the heart to tell her that the outfits she is wearing makes her look older. She worries about her age, at 38 years old, and yet she is wearing these older lady types of clothes. Then she tried wearing this yellow short nighty to turn me on and she thought she looked sexy, but it had this wierd cape type of thing with it and the whole outfit didn't really turn me on in the slightest. It just didn't fit her bodystyle, but again wouldn't look good on anyone.

I do not want to seem shallow, but I want her to feel sexy and I feel that if she knows I'm not into what she is wearing, she won't feel sexy. She told me in the past that she wants me to tell her if she doesn't look good. Then she mentioned about how a couple of her ex's gave her a hard time because she would wear some outfits in public that didn't fit her bodystyle, or her age, and it really bugged her. So I don't really want to bring back those memories for her, but I want her to look good in what she wears. And she lacks self esteem, so I feel if I ridicule her then that would only make her feel worse.

How can I tell her what I am feeling without bumming her out?

personally I would not ripple the waters or cause waves if you get my drift.  If you are happy with her I'd just deal with it, unless they are absolutely just horrible or something.

Yes you could talk to her about it, but this may or may not cause problems.  It really depends where your communication level is etc.

I would be a bit more passive on this situation most likely.  Perhaps make it a point to compliment her properly when she is wearing something you think is good.  And maybe not say much when it isn't good.

You could always buy her some outfits if you are good w/ that sort of thing and she'd wear em.

If you do talk to her, I would make it casual, like I don't like this style as much as this one or something.

Best of luck to you, please keep us posted on your situation!