Personally, as a kid, I just didn't socialise very well with girls and I preferred having boys for friends. My parents were somewhat tough on the labeling, they've been trying to push being girly my whole life. For example, when I eventually persuaded them to get me a skateboard they folded, but got me a pink, girly one. So even if they folded with something a little less stereo-typically feminine, they tried to find a girly option. I was never interested in girl's toys so I found having friends that were boys I had a way to play with the toys I wanted to as well as avoid games I had no wish to play.
The one thing I am entirely against though is labeling in marketing. Girl's stuff is pink and boy's stuff is blue. It took a LOT of convincing my parents before I got my first Meccano set over useless Barbies and that's just stupid. I liked Meccano because I loved building things. By putting it in a blue box, however, it was considered a boy's toy. There's obvious boy's toys but we don't consider lego to be gender specific, do we? So why slap a gender role on what is essentially an educational toy?
It seems to be being better addressed these days but I still don't find it anywhere close to where it should be. When I went to a toy store I avoided the pink section like the plague and my parents wanted nothing but to drag me to that section. I do feel that slapping a gender on a toy is just pointless. I'm sure there's PLENTY toys in the boy's sections at toy stores that girls would indeed be interested in and vice versa! For example, there's a lot of male chefs out there, and very often the food and kitchen toys are aimed at girls.
So I think in terms of marketing there's some very strong labeling going on especially in younger years through clothing and toys. As one grows up though I'd probably say it's easier for women to experiment over men at the beginning stage. Girls dressing in boys, or what are often referred to as "unisex" these days, tshirts isn't something one immediately sees and think "There's a TG!" Lots of girls wear these unisex tees. And girls wear baggy pants, etc. It's just a norm, especially among more sport orientated girls who maybe want to wear a football (soccer) shirt. Not every girl goes out every day in make up and particularly girly clothes. So I'd say when you're in your teens, in terms of outside sources forcing a label I'd say more for boys than girls but with leeway. Around late teens and after though, I'd say it starts to slip a little more the other way, that's how I found it personally at least. In terms of socially, however, there is some pressure I feel. If you hang around the same people all day without make up and in boy clothes, then questions do start being asked and it does start being awkward (for example a school setting).
I found it easier before puberty to not worry so much about labels, despite my parent's hangups. Once I reached puberty, it started to get a lot tougher for me. I was attracted to boys, but I felt like one of the boys myself and everything became a bit awkward. I've always had more friends who were boys, but now I actually started to fancy some of them and that got very confusing and I think that's where the label of gender vs sexuality kicks in.
However, I find it prudent to mention that one of my best friends is female, happy that way and is pretty much exactly like me in every other way. She's perfectly happy to live this way as a girl, and feels very much like a girl who just happens to hate the idea of stereotypes based on gender. And I know this friend well enough (and for long enough) to know it's not denial. So I think in this day and age, it's really hard to slap label on girls and boys with some kind of expectation of how they'll turn out. Just because a boy likes girl's stuff doesn't always mean they'll end up TG too. And just because a girl likes boy's clothing, it might turn out to be nothing but a wish for better comfort! Lol. I think parents can panic when girls and boys show signs of liking something not so stereo-typical of their gender.
I hate when people NEED to know the sex of a child or NEED to have a girl or boy in the family. In my opinion, we shouldn't assume anything based on the gender of a child, and I feel there's a lot of expectations among the majority of parents based on sex. These days girls can aspire to do anything a boy can do. Girl's being refused an education in some countries appalls us, but someone saying they really, really want a girl isn't something we question. Why? Whenever I hear something like that I can't help but think, "So, if you had a kid like me, or even my aforementioned friend, they'd be a huge disappointment?"