Haha it's never been a big deal to me. Maybe your girl in question is special in her case of wanting you to wear shoes so much.. Or it could be a number of things. Are you walking around in public barefoot? Maybe she's worried about the image your projecting and how it reflects on her, or about you stepping in something and getting ringworm, or maybe just about you possibly hurting or tearing up your feet. Or is it only at home that she doesn't like you barefoot? Do your feet smell? Do you have athlete's foot? Maybe feet just gross her out and she wants you to keep shoes on.
I guess for you to really know, you'll have to ask the girl in question.
Shoes aren't really important to me. I'd prefer that a guy wear shoes that are clean, not falling apart, and suit the outfit he's wearing (i.e. they don't stick out like a sore thumb), but other than that, I don't care.
My boyfriend was wearing these ugly HUGE skater shoes and he was 24. I thought that was gross, I'm SO GLAD he threw them UGLY sheos away. They looked so HUGE on him, he's trying to change his style of clothes and look more sophisticated and grown up and they just don't match! GEE! UGLY... but he wears jeans and dress shirts (mostly blue ones with lines, colar shirts and business casual for work). But I mean, those UGLY dim gray skater shoes were the ugliest things. Plus he hasn't skate in YEARS... so why need them? They made him look like a CLOWN, and he's super skinny (5'9 and 125) but whatever... you know? they just didn't match. Thank God he threw them away. He's now wearing super slim black and white pumas with everything, OMG looks so much better! I can't tell you how much BETTER it looks... but yeah. Ugly skater shoes -clown, little 14 year old boy, doesn't match outfits or his age... that's why!
truly shoes do not madder to me on a guy, but it shows what he likes. like if he wear sneakers, you can tell *most of the time* that he is up doing stuff and being kinda like active. if he wear cowboy boots, well I think that's plain obv. what the reason is besides he likes them. skateboard shoes, another obv. reason.