Welcome Chadwick.
I'd have to agree with my fellow SBG's. It was a liberating experience for me to go sly 3 months ago. Once you do it, any self-perception issues will likely go down the drain with your hair

. In all seriousness, you'll probably stand in front of the mirror and gawk at yourself grinning, laughing, and wonder if the decision was the right one. After a few days, you'll likely go back to that same mirror, take a sip of your mai-tai and ask yourself, "Why didn't I do this earlier?". For me, it's a cool feeling to be sly. Frankly, I can't think of the last time I woke up and immediately reached for a baseball cap. I LOVE going around town, playing golf, and running WITHOUT a hat. Before Jan. 1, 2007, I could NEVER make that statement !
By the way, we have a couple of financial SLY Guys besides myself (Robmeister & Johnny, I'm sure there's more out there). So far, I have not found any career negatives to my new look. I'd be surprised if they have either. Also, congrats on getting married this year. Have you talked to your fiancee about it? Do you think she'd rather have a SLY hunk standing next to her at the altar or a guy with a horseshoe of hair? Don't mean to be derogatory about it, but to answer your question...yes, men have a sense of vanity also.
Personally, I think I look much better with a sly look and I certainly feel much more confident about myself and my appearance, despite the fact my lovely wife HATES my new look (too bad, I ain't a-changin').
I can almost guarantee you will quickly embrace your sly look and the sly lifestyle. As corny as this may sound, going SLY is empowering.
Best wishes and I'll pour an extra shot a kahlua in my cup o' joe this morning for ya!
Schro