This success of this look, which I really love, depends on a couple things. First, the white shirt. Not all white shirts are created equal! Don’t buy a man’s dress shirt! Please don’t!! You need to buy a woman’s shirt which is inspired by men’s shirts. A woman’s shirt will have curves, created by seams or darts that flatter a woman’s shape. It needs to be the right length too and have the right kind of shirttail hem. If it’s too long it looks sloppy. It should hit just above your hip not at your hip or below your hip. Nice details in the collar and buttons and cuffs will add to the feminine allure. You want to have a nice mix of masculine/feminine not look like you are dressing in a man’s clothes.
The pencil skirt is a good idea if you can carry it off. I think it looks best just above or just below the knee. If you are short, above, if you are tall and leggy, below, if you are average, your choice! The jewelry and shoes you wear with it will keep it from looking “waitressy”. I would keep the jewelry understated and classy, probably a little modern, like Elsa Peretti for Tiffany. No sensible low heeled pumps! That is what a waitress would wear. You want the sexiest shoe you can stand (in). This is a look I really love. It is timeless. The whole masculine/feminine and dandy look is one of my favorites. A little touch of lace somewhere also helps keep it from looking “waitressy”.
Ann Taylor is a good place to look for the white shirt.
http://www.anntaylor.com/ann/product/product%3A263648/AT-FULL-PRICE-TOPS/Cotton-Long-Sleeve-Perfect-Shirt-with-Satin-Placket/263648?colorExplode=false&skuId=10045435&catid=cata000010&productPageType=fullPriceProducts&defaultColor=9000