First time wearing real men's clothes

[Jasper.Beauclair]

Ok my first time trying to pass in public: I wore a flannel dress shirt and tommy hillfigure(?) khakis
Pants from lost and found at school
Shirt from a thrift store

I only have a few pairs if shoes: black slip-on vans, yellow, pink, and blue tie-dyed slip-on vans, and shiny plastic (i think) black boots from my dad's girlfriend that go up my calves

I wore the boots because they make me an inch or 2 taller

I didn't bind because I don't have anything to bind with..
I think I did make a few people do double takes until I spoke... I have a very high voice..

but it was the first time i was very confident in public
im going to try to get a binder and things

Maybe other guys would like to share their experiences in public? I guess, like first time passing(or failing)?

[Ryan55]

I wouldn't say this is my first time going out looking like a dude, but it is most recent.

Yesterday I had to get my license renewed (cause I'm getting old and need the adult license now that no longer says under 21 until... ) anyway I'm standing there waiting behind some guy and the receptionist lady is asking everyone who enters, whats the problem, how can I help you, and I guess this guy wanted to register his truck, so I see the receptionist looking at me and she holds her hand out towards me and I see her face trying to figure out if I'm a guy or girl, was a good minute before she finally said to go stand behind that person, just leaving out he or she altogether. It kind of made me laugh, at least I didn't fail, but I didn't pass either, but still better than failing altogether. Sometimes you just need to make a joke and laugh at it, to feel better, I know in due time once T starts, I will pass better, but just have to shrug it off and keep moving forward.

[xKadaBear]

I've been wearing mens/boys clothing since I was in first grade. But the first time I went out with the intent of passing I was fourteen, and it didn't go to well. If I remember correctly that day I went to the mall with my mom and I didn't pass to anyone, but then when we went to the gas station on the way home I remember the attendant calling me sir and it made my whole entire day.

[Jason C]

I have long hair (dreadlocks) and my clothing style has always been as it is. That coupled with my feminine voice and massive bum means that I'm certain I will never pass without the help of hormones lol. I'm OK with that, I guess, so I'm trying not to get hung up on passing, though if it ever happens, I'd be thrilled beyond words.

So I can't really comment in that sense, but the first time I wore men's clothes entirely, as well as tying my dreads back as per the suggestion of someone on the site who said guys tend to wear their dreads in a ponytail, and wearing a binder, I felt awesome. Didn't speak to anyone, and people here don't really use sir/ma'am anyway, so I wouldn't know what they thought. But I felt very comfortable and confident, which is amazing considering how bad my anxiety is.

[Jasper.Beauclair]

I live in a small town and I guess I have a memorable face
Everyone still recognizes me
But going out of my town on dates, I've never felt more confident when people actually can't tell
I agree it's better than failing all together, I'd rather have completely passed
My thighs and butt are big

[Bombadil]

I've pretty much dressed male-ish but have recently gone all male (heh). I'm small and my voice is definitely female so I don't totally pass. And I also live in town so here people see what they've always seen, a female. But it still feels good to dress in male clothes and I think when I get away from people I know it's much more confusing as to what I am