Would you like this type of guy?

Recently I've been having trouble approaching women, or maybe it's due to the cold because I've had better luck during the summer. But as I get wiser and start to make more money, I become less interested in taking the initiative to approach women. When I was younger, I used to have no problem approaching anyone, but as I get older I get more self conscious. I'm a 28 year old guy with a Certified Public Accountant (CPA) license who works at one of the top accounting firms in the nation. I'm pretty good looking as most would say, but everywhere I go I get the impression that women and girls are either intimidated by me or just uninterested. How would I go about approaching a lady I see in public like on the train, walking outside, or at a bar/club? How would you like to be approached?