Panties are more comfortable than men's underwear (not all of them, granted, but I tossed the other ones), so now that's all I have. And now that I've FINALLY found a reasonably priced super-comfortable women's thong that's pretty much all I've been wearing since I found them! So to answer the OP question, I wear panties largely due to comfort, but I have to admit I like knowing that they're panties and not men's briefs, even though I have a few that will pass for men's at the doctor's office.
Bras on the other hand make no sense, I just like the way they feel, even though admittedly they're not really comfortable after a few hours. So I'll wear one sometimes under my shirt if I think I can get away with it (at least my wife doesn't care).
I never wear stockings or tights unless they're visible, like with a dress, skirt, or Daisy Dukes.
I think the largely unmentioned third category here should be women's clothes that no one notices are women's clothes. I have no male socks (boring and ugly), I have several pairs of women's canvas shoes (similar to Tom's but prettier), I only wear women's jeans and cutoffs (way more comfy!), I wear women's racerback tanks (comfy and I like the look), and a few women's t-shirts (so much softer than men's shirts) that go unnoticed. There have been plenty of times sitting at the sports bar when I've realized that everything I'm wearing is from the women's side of the store, and no one has a clue.
