Hey guys

Now that I'm on testosterone and will be exercising/slimming down to avoid the backlash of my fat redistribution, I want to get a more masculine haircut that will suit a slimmer face shape. Although I do like my hair now, I've kind of had it almost identical to this since I was 12/13.. I need a change to go with my transition. 

It wouldn't be for another few months, but I've asked for a few friend's opinion and my girlfriend's, and they like the idea of a sort of short/low pompadour/quiff with short/faded sides. I was looking up some photos (especially Morrissey.. mmm) and I'd just like some more opinions.

This is my hair now for reference (ignore me showing off my new shoes, I got this from my Tumblr )



Since I love 40's/50's hairstyles as well as rockabilly/psychobilly styles, I was looking at a haircut like these:





On the other hand, I was looking at shorter, messier, bedhair sorta cuts..





Any suggestions would be greatly appreciated 

I don't know how old you are, but from what I can see you seem to have a youthful face.  Because of that, I would personally avoid the Orlando Bloom look and the sort of unisex choppy look for now.  That top pic is how I wear my hair now and it literally has been the difference in my ability to pass.  That gradient dark-to-light/long-to-short look on the sides is what you should go for IMHO. 

My hair was like your's for years and years and I got really sick of it and got it cut similar to the pictures you posted.
I guess mine would be called an undercut, and I was really hesitant to do it at first because naturally, I have a really round face and it's kind of chubby.
But it honestly doesn't even look bad, I'm quite happy with it.
I've heard those kinds of haircuts are best with a slimmer face, so I think you should go with the short sides and longer top like an undercut or pompadour or whatever! You'll probably be very happy with it regardless of face shape 

I had hair similar to yours for probably the past 5 or so years.  In fact, aside from hair, we seem to have overall similar styles.  Anyway, I also am a big fan of 40s/50s style, particularly the hair. I finally got a cut about a month ago, similar to the first picture you posted. Mine has a little less length on top and  I do sort of a side pomp.  I felt really attached to my long hair for so long, but if I figured if I hated the short cut, I could always grow it back.

I was also terrified of going to an actual barber,but once I finally went, it was awesome.  In my area, there are quite a few "old school" barber shops that specialize in those sorts of cuts.  It was such a nice change and really, it's amazing how much of a difference a hair cut can make in terms of confidence.

I think you could totally pull it off and I can tell you from experience that it is so nice to have shorter hair now that requires so much less effort.  If/when you do end up cutting it, post a picture!

I got a haircut recently and I had the same concerns. I have a square face, but it's not masculine at all. The only masculine parts are my chin and nose. I went to just a standard hair place, since we don't really have many barbers and the ones we have are more old-fashioned. I asked for a "short, men's business/casual cut" and I love the way it turned out. Shorter on the sides and back and a little longer on the top. I don't have bangs really, but I do have a sort of fringe thing that I can brush back a little to give that 50's/60's style look.

It was great, I love it, and I have so many people tell me that I look much more masculine just from cutting my hair. If you are worried about face shape, don't worry too much. Remember, lots of cisguys have what can be considered more "girly" hair styles and lots of younger guys have a softer look about them. The wonders of youth, I guess.

I got my first ever barber cut recently. I regret it (wasn't worth paying for), but the cut I got was pretty short, and I'm passing almost all the time with it. Before I was passing probably more than half the time, but nothing near always.

Idk what advice I'd give. I know nothing about fashion or culture. Just maybe I'd point out that I tend toward more outlandish or expressive cuts, and I always pass better with more conservative ones.

Is that Morrissey?
Please cut your hair like Morrissey. xD

Indeed it is the one and only Morrissey himself.
I think I'm leaning towards the first two pictures. I appreciate everyone's suggestions and advice. Thank you all
In the near future I'm sure I'll work up the courage to get something like this done and I'll be sure to post a photo.

You can't go wrong with a Morrissey haircut. He has awesome hair!

Quote from: JasonMEW on November 11, 2011, 04:16:50 PM
Is that Morrissey?
Please cut your hair like Morrissey. xD

Agreed.

First picture! I love that hair,

not too keen on the bottom two though..

Here's the haircut I just got. I think it's fugly, but I pass better with it. For what that's worth.





Honestly, I can't wait for it to grow out a bit. I'd rather not pass than look like a freshly-shorn military recruit.

That probably doesn't help, does it? xD

You look great Felix I'm sure you'll be happy with it when it grows out a little the way you'd like it to.

I've definitely decided on the Morrissey/faded sides and pompadour/quiff style. Perhaps the Orlando Bloom pictures were a spur of the moment man crush expression, because now that I think about it, I wouldn't get my hair cut like that anytime soon

Yay.
I can't wait to see your new haircut.
:]

Quote from: Morgan (138) on November 19, 2011, 06:21:23 AM
You look great Felix I'm sure you'll be happy with it when it grows out a little the way you'd like it to.

I've definitely decided on the Morrissey/faded sides and pompadour/quiff style. Perhaps the Orlando Bloom pictures were a spur of the moment man crush expression, because now that I think about it, I wouldn't get my hair cut like that anytime soon

Thanks Morgan.

Tell us how you like your new cut when you get it.

The only thing to keep in mind when you go really short is that it accentuates other things. If you have a naturally found face (even with fat redistribution your bone structure may still be more soft/roundish) that will accentuate it. Also, anything short on the sides is going to accentuate the fact that you don't shave (some guys have to wait quite awhile on T to start shaving) and therefore might look very young or make some people think lesbian or butch over male.

You could go for something like this too, which is a lot shorter but has a slight messy thing going on


This seems really similar to what you were mentioning ...


and to contrast, here's a girl rocking a similar cut - so until T really kicked in and you were able to get some facial hair going on, you might have to play around with the sides.

The date is set! Morrissey haircut is booked for Thursday morning at 10:30AM. I'm excited, but anxious! I haven't had short hair in a very long time..

Quote from: Morgan (138) on November 21, 2011, 09:14:22 PM
The date is set! Morrissey haircut is booked for Thursday morning at 10:30AM. I'm excited, but anxious! I haven't had short hair in a very long time..

Awesome. I can't wait for pictures.

So the deed is done! I decided not to get the sides TOO short, because I didn't want to be sitting with my hair so dramatically cut that I sit and play with it and try and make it look like it did when it was long. This is the shortest I've had my hair in a while, but I don't think it's insanely feminine, and it's not as curled/styled as it was this morning (it's been raining all day ) but I do like it!

Can you put up a more side shot pic?