Cowlick Problem

Hair cutting
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Q: Thanks for putting together such a helpful website. I have stick-straight, thick, blonde/light brown hair. For the last decade while I was in college and traveling I have taken the ultralow maintenance route to taming my cowlick: I cut my own hair with an electric trimmer set to 2 (1/4") or 3 (3/8"), so that it all sticks up evenly. And I typically wear a baseball cap either all day or for the first part of the day, so that I can get it to lie down. My cowlick is on the top of my head in the back middle and really stubborn.
My fiancé doesn't like me wearing a hat every day, and I empathize with her. I've let my hair grow out for the last 7- 8 weeks, and now it is about 1.5" all around. This is longer than it has been in 15 years or more. I'm now willing to consider going to a professional barber or even a salon so that I can try out something that has style and also to keep my wonderful fiancé happy.
I would consider the Caesar style, and I am willing to put gel or some other product in my hair for her. But my hair is stick straight, so is this a style that might work for me? I would prefer to keep it relatively low maintenance, and I generally assume the longer the hair the more maintenance. Is that an accurate generalization?
I wouldn't mind having my hair tapered so that it is longer in the front and on top, but shorter on the sides and in the back. I used to do this when I played soccer in high school, but I don't know how I could keep it professional. Is that look a possibility if it was gradually tapered and I got it to lay down?
I tried a faux hawk. I liked it, but I wonder if it is possible to make it look professional? Another thought: if I grow out my hair on top and want to keep it short on the sides, say a #4 (1/2") and the top, at what point will the disparity make it difficult to keep it looking good?
One other concern is that my hair sticks straight up everywhere. Imagine a blonde mini-afro! Once I wear a hat, it goes down, but even with gel it likes to poke upward. Would this problem be alleviated if I had my hair thinned out a bit? My old hair stylist used to do this many years ago. My hair is really thick.
My fiancé wants me to grow it out longer, but I am active and go to the gym daily, and I don't want hair in my face or over my ears. Hopefully, I can find a short style, and with a bit of styling she will compromise with me and let me keep my hair moderately short. I'd be totally willing to have my hair 2-3" long on top if I could keep it short on the sides. I think if the cowlick part of my hair is longer than 3/4" and shorter than 2" it is really hard to control.
Also, I think my hair grows about one inch per month. Is that about average? Perhaps I should mention I am addicted to exercise. I'm 29, and I work in sales. My current job allows me to wear a hat most of the time because I'm outside, but my next job (which I am looking for currently) likely won’t allow it. Whew, that was a lot longer than it should have been. Sorry, and thank you so much for any and all help.

A: Wow. This is a lot of questions. Let’s try to cover everything in a simple but comprehensive way. Your cowlick problem is common, and if you know the length limits your hair has in order to be manageable you can make a look that is flattering and low-maintenance. The level of effort needed in styling the hair depends not only on the length but on the texture and wave pattern as well.
With straight hair as you describe, you can probably be comfortable with the Caesar cut you mentioned with the majority of the hair on the sides, back and top cut to around one-half inch with a slightly longer fringe. Another option would be the Collegiate Cut, which has very short, tapered sides and back – even into the crown area, but which grows longer as you move forward along the top of the head. The Collegiate Cut is usually 4 inches long or so in the fringe area. This may satisfy your fiancé’s desire for the longer hair, without making you deal with a style uncomfortable for you.
Thinning the hair may be necessary if your hair is very thick, and having the hair thinned will make it easier to style and deal with. Styling product will also help, and given your description, I recommend using a wax-based product, like pomade. These are stronger in hold and yet remain malleable.
The best part is that with the Collegiate Cut, the longer length in the fringe is easily styled for a neat, professional appearance. In fact, in the late 50s and early 60s, when the Collegiate Cut was prevalent, the cut was often worn slicked back or swept into a flip-over style for dressier or more-professional occasions (like work and church) and worn casually styled with a loose fringe.
As to the rate of growth you describe, I can only say that the average person’s hair grows a one-half inch each month, and the idea that your might grow at double the normal rate seems unlikely. I WILL say that because you generally keep your hair cut so short, the hair will appear to grow very rapidly. If you get a one-half inch of growth in a month and you generally keep your hair cut to a one-quarter inch, then the length of your hair will double in only two weeks, and therefore appear to be growing at a rapid rate.
See also: Men's Hairstyles