I am a happily married boring middle-aged guy. I am on styleforum. I notice clothing. I look like a poor man's Matt Lauer, complete with the exact same haircut and thinning hair, i.e. I'm no Tom Brady. About a month ago, I'm having a few drinks w/ friends, I'm standing at the bar ordering a round, this rather attractive girl significantly younger than me is also ordering drinks, wearing kind of a cool leather jacket. I tell her I like her jacket. This leads to a conversation of how she thrifted it, got it for $30, I tell her how I got a cool sport coat on eBay for $40, blah blah blah, we could have talked all night, but my friends finally yell at me that they want their drinks. So I say sorry I have to go, and she says "too bad," then she says "wait a minute." Digs in her purse and gives me her phone number and says something along the lines of she really enjoyed talking with me and would like to again some time.
Of course, when I'm single, I can't get a girl to talk to me, but now that I'm married, women are interested left and right.
Anyway, the point is, compliment one of these girls on their earrings, sandals, whatever, a good icebreaker, and go from there.
