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Sissies forced to wear their hair short
I know many sissies and their Superiors prefer a girlish hair style be worn, all the better to appear to be more 'femme'. 
But then there's another side to a sissy's hair length, that of having to wear a short 'boys' cut with their frilly and girlie garb.  Think short-back-and-sides, a crew cut, a bowl cut, even the head shaved bald.   Then there's no hiding the fact the sissy / petticoatee is an emasculated male, a little boy 'child'.  Exposure like no other. Frightening. Humiliating.   

Here's an image I found that captures this approach nicely.  Unknown artist.  

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Ah, the dilemma! 

No boy wants the embarrassment of knowing they look so girly that they regularly get mistaken for an actual girl, and will want to cling on to any remaining vestiges of boyishness.
Yet having a boys' haircut will show everybody that you're cleary a boy wearing girls' clothes.

You can't win.
When I was a child and a teenager my mother used to offer me the choice:

1) having my hair cut in a normal boy's style, which looked good most of the time, or

2) leaving it a bit longer which meant that when I was being punished by being made to dress as a girl she could make my hair look girly too

I reluctantly went for option 2.
Probably the best choice Ali as you could (I imagine) get away with it being a longer boys style or a girly one.
I know in previous posts you've said that your mum never made you go out in overly girly dresses, but were you made to go out as a girl (complete with hairstyle) and did you get accepted as a girl by the public, or was it strictly kept at home? 

My punishments were mostly at home, but the threat of being taken out in a dress was always there.

I did occasionally get taken out dressed as a girl, and sometimes in a nappy too.

One time that really sticks with me was when I had been put into my sister's school uniform, and got taken to collect her from her school. It was so embarrassing having to get out of the front seat and climb into the back wearing the same uniform as Lucy and her friends, except that I had on one of her gym skirts, so much shorter than the skirts they were all wearing. I'm sure they saw my knickers.
Ali, I agree and understand your choice about hair style. With my dressing as a girl as much as I did as a teenager, I went for a style that could be changed fairly easy to being girly rather than looking like a boy cut. Being seen with a longer bit of hair (even though the rest of your clothing said you were a boy) really wasn't that bad. But having a short obviously boy-style haircut that let the world know you were a boy in that pretty dress or skirt was horrid.
Yes, absolutely.

But having slightly longer hair meant that my mother would sometimes say, even when I wasn't being punished, something like "Your hair's looking pretty, Ali." I'd blush beet red, knowing that I was only a moment away from having to be dressed 'pretty' to match my hair.
Those casual nods towards petticoating are some of the best parts of any story, real or fiction.
It must play straight into your fears and worries;
If you're not being punished, the comments might be in front of people who don't know you are regularly petticoated, and make you worry they are going to start wondering/questioning, or that you're moments away from punishment starting again.
Alternatively, if you are being punished and are say dressed as a girl, people may assume your are being made to wear a dress, and that's all, yet a throwaway comment might lead people to think that maybe you just might be wearing a nappy under that dress.

The worry is almost as bad as the punishment itself.

Hi all,

Mistress has always insisted that I wear my hair in a short masculine style. I am 6 feet tall with broad shoulders and to finish off any pretence at all, I am required to have a moustache.
When I am serving Her and Her friends/lovers there is to be no doubt that I am her feminized submissive husband.
When out and about in ladies slacks and a blouse, I am to be identified as a man in feminine attire, mind you my handbag tends to be a bit of giveaway.

I do have wigs to wear if Mistress decides I am to appear more feminine but the moustache stays.
Aren't our superiors wonderfully inventive.

Oh Sarah, a moustache - eeeeekkkkk! You poor, poor thing. I'd be mortified if my Superior made me grow either a beard or a mo to contrast my sissified dress. Nowhere to hide.

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