For over seven months of dating, I've told my boyfriend that should he ever want to go out dressed up, I more than welcome it. A few times, he's gone out wearing a skirt to what he considers a safe space. A regular hangout with people he knows or friends houses. Well, a week or so ago, one of our friends had a huge event planned to propose to her girlfriend. This was at a local bar/hotspot we all frequent. However, only a small portion was reserved for her event and it is a fairly large venue on a Friday night, so lots of people we don't know also there.
Despite the uncertainty, he decided to get dressed up. He doesn't have fancy blouses (yet!), but he wore a cute skirt and pink top. No girly sandals, so just wore leather flip flops. And he did the most makeup I've ever seen on him. He doesn't look femme, but he still looks cute. Anyway, we went to the event and no one gave a negative look or uttered a rude word! He was completely embraced by all of those there for the proposal party (or whatever that type of event is called!), and no one else there seemed to care.
And we even left that event for a bit and walked several blocks (we were downtown) to a hotel where another of his friends was having her birthday party. Same deal. He only knew a few people there, but no one seemed to care in the slightest that a man was there in a skirt and girly top and makeup. So it was a great boost to his confidence is going out dressed. So now I'm looking forward to the next evening out. Maybe he'll wear a dress next time, or we could buy him a cute top or two. Oh, and I bought him some pink flip flops! (I bought my daughter a pair, and he liked them so much, I had to get him a pair too!)