I mean I do not want to be harsh on your boyfriend but that is a little bit stupid unless he is just charmingly disarmingly naive/innocent maybe? I mean, yes, I think it is possible someone could wear that and just look totally sincere and comfortable with it, but it is a really short school-girl skirt in case we all hadn't noticed yet. If you really want to wear it out, you could do the full-length tights/stockings thing, but I think that's a little lame personally. Maybe you could just try wearing your favorite, most comfortable, personal top and see how you look/think of yourself with it?
You need a top that projects 'yes this skirt is me I think it looks nice and I like it and I do not think it makes me look skanky'.