It's comfortable, forgiving, you don't have to worry about bending over when you drop your keys. But how does one wear it without looking like a reject from the year 2003? Stick to solid colours, patterns tend to recall either an aging art teacher, or a member of the Holiness sect. One of the biggest supporters of the long skirt was Olivier Theyskens when he worked at Rochas.
His designs look both terribly modern, and wonderfully romantic. I wouldn't suggest wearing them with a high neck or long sleeves. I fear you would too closely resemble a character from a du Maurier novel. If you have long hair like myself, don't wear it down, it will look too heavy. And unless you are super tall, wear long skirts with heels, but make sure the skirt isn't so long that you're tripping over it!
You can find a long silk ball skirt in pretty much any consignment shop in the country.Keep it simple with a delicate tank top
And to keep it young, add a leather jacket and plenty of jewelry.