Welcome CW, I think the sly look would look really great on you !
I think about a week ago I was in the same situation as you are - everyone on this forum told me to shave and that I'll look good and that it will do good for my confidence. I was thinking about shaving till november and at this time my confidence was at an all time low (break-up with my girlfriend and hairloss - what a great combination) I was sure that I would have to be alone from now on

and then last week I did it and at first I wasn't happy at all and now I'm one week in and bekieve it or not I feel great, my confidence is back and I finally for the first time can accept my looks and dont have to worry that anyone will notice my hairloss and think badly about me.
You look good on that photo and I think a buzzcut or shave will fit you - so now I'm one of those anoying "just do it" people too

do it! I'm sure you'll also think why didn't I do it earlier - but you might have to get used to it - but I'm sure it will look good on you
You won't know until you try. Go for it, I know you will love it.
Go for it. You won't know until you try
Thanks for all the encouragement guys!
I've taken your advice and am walking myself into it..albeit slowly! Went to my hairdresser and she graded it from a 2/4 at the sides to a 6 on top. I know that's pretty long for most of you on here but it's the shortest I've ever had it!
Already liking it, I'll give it a week or two and then go a bit shorter. Thanks again
You are on the right track mate. You'll know when you are ready for the next step
That's a good beginning. When I started heading for shorter hair, a buddy and I did it together. I told the barber I wanted what he had. I'd guess it was about a #4. I liked it. Then kept going shorter and shorter. The shorter you go, the more frequently you need a hair cut, so I took on the task myself. The shorter lengths are easy enough to do yourself and save the expense.
When I got down to the #1, my friends questioned why I did not just shave it bald. I was almost there and they said I'd like it. And I did.
Welcome to the forum. Start with a buzz cut, gradually clip it closer, and before long you will want to shave it down. Guaranteed.
I think the only goof is the person who doesn't try it. Go and try, and come back; show us a picture when you eventually do it.
Do it, you can always grow it back to where you are! (maybe it will take a while

)
I've been buzzing it lately and it feels great, I will go as far as saying that I don't like how I look if I leave it to grow too much