Hello,

I've been trying to up my style a bit and look more like a man and less like a boy. I used to be a t shirt and jeans only kind of guy. When I got a haircut it would be super short so that I wouldn't have to go back for as long as possible. I'm trying to change all of that and find a style that I'm happy with.

Well here is a picture of myself about a month after my most recent haircut. I was trying to clean up my look and go for sort of a Don Draper kind of thing but I'm not sure I completely like how it looks on me. Maybe it just needed to be cut better... I don't know. I didn't get to go to my usual barber so I settled with a guy I hadn't been too impressed with in the past and got what I got.

My face is fairly round as you can see, so I understand I need more of a square haircut from what I've read on here. I'd like some comments on the following styles on me:

I still like the Don Draper look as well... if you think it can be salvaged on me somehow, let me know.

I'm interested in some of the more retro/ classic looks. My hair grows fast, it's wavy, and it seems to grow down just fine and spike straight up just fine. It usually doesn't give me too much trouble except for the fact I never know what to do with it.

Any advice would be much appreciated.

Thanks!

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Hard to say.  Look at more pics to see what you like, and tell the barber, do that?  The looks you post here seem pretty plain vanilla, and should be easy to achieve, I'd think.

The style you've gone for is good. Maybe trim the sides more like a "contour cut". In my opinion nothing beats the classical styles of the 20's to 50's. Also invest in some good old school pomade for the sheen.

Personally, I'd base it more off a whole picture. Do you tend to dress more refined, or laid back? Are you planning/capable of growing facial hair to pair with it? I'd say the second cut would be fine with just about anything, but the backswept would look fantastic with a mustache or circle beard and some spiffy clothing.

I'd love to see the B&W style on you.  I really like the "long on top/buzzed very short on the sides" look.  How nice that your hair is thick, and also grows fast.  Have fun!

Actually, it's true that your face is round, but it's fairly small and your forehead is huge.  It's just the way you're proportioned.  Consequently, a forward swept style might be more flattering, because it would visually shorten and therefore balance out the proportions of your face and hair.

 

Unless you have your heart set on an upswept style, you might try something like this:

It can easily be made neater, with a side part...but by bringing the hairline down, visually, it makes Tobey's huge forehead look more balanced.

 

George Clooney is also well served by the same trick.  It's subtle, but it works.

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