My hair has been long all my life (like, down to the middle of my back long - mostly because my parents didn't let me get it cut shorter.) Well, lately i've compromised with them on what i consider to be "medium" length (my dad actually CRIED when i first got it chopped off.....  ) and now that i'm transitioning i'm ready to go short.

What's the best cut to go for (especially for my plumper face until i lose the weight)? Any suggestions?

Depends on your face shape.

I tried loads of those hairstyle sites to get an idea about what shape my face even falls into (none of them apparently. ¬.¬), so I could figure out what might suit it. But in the end I think what "suits" a face is only about what expectations people already have.
For my first short haircut ever I took some photos of an androgynous style on two different androgynous looking people, figuring that would be the best approach for now. I don't care if it's what people expect for my face shape (though people who know me as a straight female say it looks good just the same as people who know me as FtM), it just feels hugely liberating!

I'd suggest going for something /you/ like the look of, personally. (:
If you really can't decide, perhaps take a few different pictures and give your hairdresser (If you trust them. I went to a particular guy on a recommendation) the freedom instead, they are trained in knowing what styles will look good on your face!

Judging by your picture I actually think the cut you have there is pretty passable.  Any shorter and you're risking a butch lesbian look.  I've always kept my hair a bit "long" (for a dude) i get it cut with the "bangs" at the bridge of my nose and at around low/mid ear level on the sides.  Its shaggy and stonerish. (but then again lets be honest so am I so it fits)  Too long and I look like an androgenous nerdy dykey girl, too short and I look clearly feminine in the face.   

its really about balance.

Leave it as is, or if you still want to shorten it there's the classic short back and sides cut. A crew cut will probably make you look like a lesbian.

Quote from: GnomeKid on December 02, 2009, 02:47:57 PM
I've always kept my hair a bit "long" (for a dude) i get it cut with the "bangs" at the bridge of my nose and at around low/mid ear level on the sides.  Its shaggy and stonerish. (but then again lets be honest so am I so it fits)  Too long and I look like an androgenous nerdy dykey girl, too short and I look clearly feminine in the face.

This is so me. I compared pix of my mid-back, just-above-shoulder, and short haircuts I've had, and the shoulder-length stoner shag actually is the most masculinizing for my face. Funny how hindsight is 20/20

Quote from: Banf on December 02, 2009, 02:34:11 PM
If you really can't decide, perhaps take a few different pictures and give your hairdresser (If you trust them. I went to a particular guy on a recommendation) the freedom instead, they are trained in knowing what styles will look good on your face!

I need to FIND one first, lol! I've been using the same one for the past year or two and (even though she does a really good job with my hair, which poofs out like an afro when it's cut the wrong way) every time i go in and say "i want it short" she always tries to make it look "more feminine." *eye roll*

Somehow that always ends with her leaving little tufts over my ears (covers them) and i end up chopping them off at home lmao! Haven't said anything before now though because i could chop the tufts off.

Guess I need to find one that'll do an equally good job with a more masculine cut, now.

Oh, and you can't really see in this photo but it IS kinda long in the back - the vest just hides it. I'm looking for shorter back and sides but i don't think short or no bangs would work for me lol. Not yet, anyway!

Quote from: FolkFanatic on December 02, 2009, 05:44:52 PM
I need to FIND one first, lol! I've been using the same one for the past year or two and (even though she does a really good job with my hair, which poofs out like an afro when it's cut the wrong way) every time i go in and say "i want it short" she always tries to make it look "more feminine." *eye roll*

Somehow that always ends with her leaving little tufts over my ears (covers them) and i end up chopping them off at home lmao! Haven't said anything before now though because i could chop the tufts off.

Guess I need to find one that'll do an equally good job with a more masculine cut, now.

Oh, and you can't really see in this photo but it IS kinda long in the back - the vest just hides it. I'm looking for shorter back and sides but i don't think short or no bangs would work for me lol. Not yet, anyway!

Solution: Cut your own hair. It's not really very hard and you will end up with the style you want.

lol, added bonus...in theory at least guys are more likely to go the cheap route and chop at their own hair than girls that care about their hair (with the exceptions of people that know how to do hair of course)....I seem to come off with more passable haircuts with the homemade chopped up "I don't know what I'm doing and I don't give a ****" hair than letting someone else have it.

But then, I'm stuck with a normal unisex hair salon vs a barber. The only barbershop near me is one of those "Lady Jane's" shops where they actually have big screen tvs with recliners and well-endowed women cutting their hair. No way in heck they'd cut my hair without a LOT of strange looks.

Quote from: Christian >.> on December 02, 2009, 11:47:59 PM
....I seem to come off with more passable haircuts with the homemade chopped up "I don't know what I'm doing and I don't give a ****" hair than letting someone else have it.

And as a guy, screwing up your own haircut isn't a big deal. It's win-win. Mess up 'till you get it right. Nobody cares.

Quote from: Lachlann on December 02, 2009, 12:11:18 PM
Depends on your face shape.

Yes, seriously.  Forget what all those "FTM passing tips 101" sites claim, there is no one men's haircut that will magically make you pass, nor will it automatically angrogynise your face. 

Lifestyle also plays a part in it -- if, say, your main social groups were hippies (as an example), letting it get too long without facial hair may seem automatically feminising, but keeping it just to the shoulders won't set you out too far from your friends, which would aid in blending in.

Quote from: Christian >.> on December 02, 2009, 11:47:59 PMBut then, I'm stuck with a normal unisex hair salon vs a barber. The only barbershop near me is one of those "Lady Jane's" shops where they actually have big screen tvs with recliners and well-endowed women cutting their hair. No way in heck they'd cut my hair without a LOT of strange looks.

Guh, that's horrible.  That's not a barber shop -- that's a Hooters with clippers.   

Quote from: YoungSoulRebel on December 03, 2009, 03:16:49 AM
Guh, that's horrible.  That's not a barber shop -- that's a Hooters with clippers.   

ROFLMAO - Hooters with Clippers

On another note, i think i found a style that i like (with a little modification.)

that's actually not too far off from my face shape...I should try doing that to my hair. Sadly I'm cursed with soft, wavy hair too >.<

Quote from: Christian >.> on December 03, 2009, 08:48:58 PM
that's actually not too far off from my face shape...I should try doing that to my hair. Sadly I'm cursed with soft, wavy hair too >.<

So was Roger Daltrey.  Didn't stop "the ladies" (and gents) from finding him lickable even at 5'4".

Wow I didn't know Roger Daltry is as short as me. Bet I can sing his stuff even better now with my slightly more dude-ly voice these days.

As for a haircut, get a fade!

Quote from: Alex_C on December 04, 2009, 12:02:25 AM
Wow I didn't know Roger Daltry is as short as me. Bet I can sing his stuff even better now with my slightly more dude-ly voice these days.

As for a haircut, get a fade!

Yeah, he's way shorter then he claims in interview -- i can tell from photos of him in places in London I've actually seen, and (assuming without hair) my half-sister in the UK is 5'4".

Quote from: YoungSoulRebel on December 03, 2009, 03:16:49 AM
Guh, that's horrible.  That's not a barber shop -- that's a Hooters with clippers.   

Dunno, I have a female barber (and she's only a barber, doesn't do women's hair) and the odd boob in the ear when you're getting a trim is not a bad thing. 

That's not a barber shop -- that's a Hooters with clippers

You say that like it's a bad thing, at least they don't have those world's worst wings things they make you eat.  My barber shop is way old school, still have 'men's mags' like Playboy to read, cold beer in the fridge, and a constant conversation about what's wrong with the Giants/9ers, depending on the season.

Quote from: tekla on December 06, 2009, 01:33:57 PM
That's not a barber shop -- that's a Hooters with clippers

You say that like it's a bad thing, at least they don't have those world's worst wings things they make you eat.  My barber shop is way old school, still have 'men's mags' like Playboy to read, cold beer in the fridge, and a constant conversation about what's wrong with the Giants/9ers, depending on the season.

You go to a barber shop still? O.o

I grew up and live in theater and when I want hair I yell 'wardrobe' and they show up with all the kinds of hair I might ever want.  Not really, I open the closet and pick what goes best with what I'm wearing.  But my own hair is very gray, and extremely fine, so its just as easy - if not even better - to just select the hair like the rest of the outfit and leave my own hair cut very short.  Illusion is the reality that most people want anyway.