I had the same problem for the first day or two.  I thought about wearing a hat when I went out, then decided nope, this is me now, I'm going to show it.  Later when I was in a crowd of people it was actually better no longer wondering who was behind me seeing my bald spot and what they were thinking.  At least they know that this look is my decision and not mother natures.

Bulls_Fan, you're missing a lot of headrubs.  The Sly look brings out the character of your face, a strong face, and centers it on your eyes.  The gals are going to reach out, trust us, and you'll be the center of attention--and not for the flagging hair setup.  The guys, particularly any that have the same genetic advantage, are going to come up and confide that they've thought about it too, then, between the babes, and giving advice on doing it, you won't have time to worry about anything negative.  Go out tonight and live, I remember the movie Mame, where she tells her nephew, "The world is a banquet and most poor fools are starving to death!"  Go on out there and feast on the banquet, you're looking good and you own it!
Just one thing, report back, I'm looking forward to a great report. 

Bulls_Fan, don't just have the look, own the look. You just have to go with the attitude, this is me.
It's kinda like sex for the first time with someone new, do you cuts the lights out before you undress or do you rip your clothes off with the attitude of "This is me and I'm about to rock your world!!!"
In a matter of seconds who the hell cares if the lights are on 

True story... My sisters birthday was in december and my brother-in-law asked if I could bring the entertainment (meaning my DJ/KJ equipment) for her party at a house he rented. I agreed,love my sis, and I showed up and started setting up in the house. I hadn't seen her or him in about 6 months, and was working out, lost the glasses, and have the goat. While setting up all of a sudden I heard, OMG, thats my brother's ass I have been checking out... is he sexy or what??
My sister was standing in a group of her friends and they didn't even realize it was me. Needless to say it was a fun night from that point forward.
My favorite phrase to use when people I haven't seen in a long time ask me where my hair is...... I decided to bring sexy back!
So bro, go out and have sex with the lights on, you will be glad you did!!

Hey man;

don't know what more to add to these excellent posts; except to give you a bit of my testemonial.   I went sly at 53 ...  a lot older than you;  but did it because my hair was sooo   thin on top; very grey/white ; and it made me look ...  well; old and stodgy .    I went sly very slowly ; and felt pretty self conscious at first .   I enjoyed going out to places where NOBODY knew me .   It helped me gain confidence and even PRIDE in my appearance -- and courage not to feel so self conscious when i was around people I know; when casual acquaintences saw me sly for the first time ...   A breakthrough was meeting up with someone I hadn't seen for a few months ....    I just walked up to him, started a conversation, laughed, smiled; and just watched his unspoken reaction.   My unspoken words were "I look good like this, don't I ? " .....   So it just takes a little time; a little convincing of your self that you look good  (and you do, by the way; you wear the sly look quite well) ....   so ; don't worry ; go out there and live life ....    and you'll meet that special woman who really digs your total slyness.

Hey

I had some self confidence issues when it came to being out and about and sly, mainly because there was no one else sporting the look at the time. Also because people were so used to me having spikey hair.

I think the most important thing is feeling comfortable in your own skin. Literally. I think the look suits you.

Have fun with it