-They're always gonna use the "I'm older so I know x" line on you as a shyt test, so always have ammo for that.
-Salsa clubs, Lounge's, etc. Basically, you want to increase the time + proximity aspect as fast a possible. Moms are essentially losers with limited time on their hands. So once you break the ice, you're pretty much in. You'll also get laid in no time, the only problem I see, is how well you can talk. Get good at dancing, and you can get some spanish milfs.
As for apparel, keep it simple, not hood, but simple. If I'm going to a popular cougar spot, I usually just do a simply Nirvana or Misfits Tee shirt, with black jeans, gives them a point of reference to how much I love music and what I can talk about.