I wear women's socks exclusively, because I like the patterns. No one knows they're for women, and I'm not sure what the real difference is since feet are all pretty much shaped the same. I also wear women's jeans exclusively because they're more comfortable. Same for underwear. I really don't consider myself crossdressing when I'm at the sports bar in those things. I wear racerback tanks to work often, marketed for women, but I see other men in racerbacks too. The women's are softer and more comfortable.
Leggings are pushing the boundaries, but when I travel in black leggings I really don't feel like I'm crossdressing either. I've noticed more and more people travelling in pajamas, I'm assuming for the same reason I'm in leggings: comfort.
BUT, I'll admit wearing such things also somewhat calms the pink fog, because at some level I know I'm wearing stuff that a "real" man wouldn't.
AND last weekend my best friend was hanging out with us, he made a joking comment about my "yoga pants" (they were leggings, I don't really know the difference.) I told him my wife plays with my butt more when I'm in leggings. My wife readily agreed. He accepted his loss and had to agree that it wasn't so gay after all.