As a kid, I was the neighborhood tomboy. All the boys in my neighborhood wanted to hang out with me, eat junk food, and play video games. I used to also play in the dirt and do pretend shooting while all the neighborhood girls played tea parties. Someone from my school actually made a complaint because she thought I wasn't dressing nicely. I used to have holes in my jeans because I really didn't care what I wore, they were going to get messy anyways! Then once I turned 12, my dad decided to ship me off to my mom on the other side of America from where I used to live. He wanted my mom to teach me how to be a lady and it worked!
Haha I have to do it almost daily because of my profession, I'm a pilot so I have to wear a black suit with white shirt and some kind of a tie for girls that is a bow, even sometimes prefer the men's ties, haha. I also instead of the jacket I wear a black pilot sweater. But I always try to be a sexy tomboy while in my uniform. Lol.
Absolutely, guys clothing is insanely comfortable. I wouldn't call myself a tomboy since I do enjoy dressing up in more 'girly' clothes but when it comes to things like t-shirts and hoodies I definitely prefer guys clothing.