How Do You Allow Yourself to Be Yourself?

Raised by a man that told me that feelings are for women and that men are logical, I have always felt self-conscious as the more emotional one of my siblings. Feeling like I was never going to measure up to the tough-guy standards I did always try to seem that way. My family and extended family are military people and I knew in my heart that I couldn't do what they did, but I always wanted to.

So I began to wear one of their hats. Didn't say anything about their service or rank, but it had the ship name on it and I loved it - even hung it up in my room so I could see it from my desk. Today I come across a professor who had served and he asked me about the hat and I just kind of froze. No one usually asks about the hat, I just get to wear a fun hat and keep the sun out of my eyes, feeling like I'm carrying the toughness that all these guys before me have with me throughout the day. But when asked I froze, just barely getting out that I'm "from a military family". He started to go on about ranks and being a captain or something but I kind of just tuned out. Now I'm not sure if I want to wear the hat anymore. I don't want to give the impression that I'm trying to be something I'm not, I just feel better wearing the hat.

So how do I go about being comfortable with being this feely blob of awkwardness that sticks out like a sore thumb in the family and among my peers?