Hellobee Boards

Oh sure.
When DS was six months old, we went to a friend's wedding, and when we went to the DRESS rehearsal, well, DS wore a dress.
It was adorable, plus he thought it was awesome to have this toy that was attached to him (the skirt).
Then he was a ballerina for Halloween, and he probably wished he could wear a tutu every day. (Again, toy that you can't drop!)
DH couldn't care less- he thinks it's weird to make a big deal out of what DS wears, no matter if he's wearing boy clothes or girl clothes or a dinosaur costume. I'm sure DH would let me put makeup on him (on DH) if I really wanted to, but he'd probably think it was weird that I wanted to.
I wouldn't do it if it bothered DS, but he's 9 months old. It's not like he has any clue what's going on when it comes to clothing.

I have a daughter but I used to have a boyfriend with eyelashes that were 10 feet long and I BEGGED him to let me curl them and then put mascara. He actually let me.

I've only done hair clips as well. Oh and a high pony tail once.

I've done the headbands and hair clips. My DH hates it but LO loves it! And he totally looks like a girl with my bow headband on. I love it!

I've definitely done this to my little cousin!

Haha, I don't think I would if I had a son.

@Andrea: Wouldn't doll him up or wouldn't lend things? Bob

My husband's sisters would dress him up as a girl, take him out in public and call him by a girls name. Like, if his name was Stephen, they called him Stephanie.