"I think that playing dress-up begins at age five and never truly ends." Kate Spade
I'm not the most competitive person. In fact I often get myself in trouble when playing games with my family because I cheat for the other team (so my own team gets me in trouble...).
It's interesting that I now find myself in a relationship with a man who is quite possibly the most competitive person I've ever known. He often has to restrain himself when playing games with my family to keep from getting in trouble. He really hates losing.
For me, the feeling of winning just never feels as good when I know someone else had to lose.
While I'm afraid it might be an inherent part of my personality, I think it increased from playing games with my friend Sara when I was younger. I wasn't allowed to win in Monopoly. Winning at Capture the Flag wasn't worth the trouble it got me in. She also made me walk behind her when we'd go anywhere because she was superior (note: Sara no longer behaves like this and is a very kind person).
The newest Crew Cuts email was a throw back those old days together. I'm not sure which girl is in charge, but they've definitely got the old Sara attitude going on.
But if you can look this cute and still have an attitude, I say go for it.
(PS: I would gladly wear either of those outfits. Dress up? Psh.)