My nickname used to be FRU-GAL... that's how frugal I am!!
I go to two specific thrift shops, one on Monday and the other on Tuesday, that sells upscale clothing for very little. I've dressed my son and myself that way since he was 5. Everytime he outgrows something he goes up on eBay. BTW, I've been getting compliments on his clothing from his teachers since kindergarten, why not, Ralph Lauren Izod and Bill Blass for $3.50 apiece???
I own Coach and Kate Spade bags that I spent no more than $15 on... I'M CHEAP but I like quality!
I clip coupons and buy items ONLY on sale and taught my son to do the same. I go to flea markets on the weekends and what I don't keep I sell on eBay.
I go to restaurants that I secret shop at least twice a week. The other restaurants I go to are via the certificates on restaurant.com.
I found my house and everything in it on Craigslist and freecycle. When I want something badly I buy it, and most of the time I return it or resell it. I bought a beautiful dinette set, kept it for 3 months and sold it for twice the price I bought it for. I also bought a front loading washer and dryer from Craigslist only to sell it when I got a house with one already in it for the same price I bought it for two years earlier!
Every weekend I check "moving sales" in Atlanta on Craigslist and find the people who are moving OUT OF STATE or the COUNTRY and get lots of furniture and appliances for FREE because they cannot move them~!

I keep some and sell the rest.
I'm a moderator on Freecycle, so I get lots of items quickly there. I also give away lots of stuff because I do believe you get more when you give.
Sure, I'm cheap... but my kid and I live very well and go to Orlando 6 times a year for less than $300 a pop. I make deals with owners, hotels and use Priceline, Hotwire and every discount you can imagine. My last trip in January included free airfare thanks to a very generous DISer, an extremely low rental of a 3 bedroom condo near Universal and a $36 rental car!!
And Michael...the poor kid thinks we're doing well!

Little does he know he has a destitute single Mom who knows how to pinch a penny till it screams.