Every once in a while I run into someone fascinated with vintage clothing, but who says, "Oh, I could never get away with wearing vintage." She seems to think that to wear vintage clothing you need Kate Moss's body and Cher's courage. My advice is to start off with a vintage coat.
Coats are one of the great bargains of the vintage world. For less than $100 you can walk away with a 1960s cashmere coat with a silk lining and buttons more spectacular than jewelry. Try that at Nordstrom and you'll be at least $1,000 poorer, and the coat's lining will rip out before the season is over. Coats made more than 40 years ago were made to last, and last they do. I have one coat with seams reinforced with velvet patches. It wears like iron.
Style-wise, a coat is relatively low risk, too. People who are self-conscious about wearing vintage know that they take off their coats once they're inside. (I love my vintage coats enough that I'm tempted to parade around a bit first.) Plus, vintage coats come in fabulous colors and patterns that you can't find today. When you're wearing mostly black, as many people do, nothing beats a vibrant coat. Some vintage coats even have designer provenance--Balenciaga designed for Lilli Ann from time to time, for instance.
Xtabay has a great selection of coats right now. We have a vintage Burberry raincoat, a camel-colored vicuna coat from the 1960s, a gorgeous orange and green tweed swing coat, a pink leather jacket perfect for Fonzi's girlfriend, a pumpkin orange mohair coat with a princess skirt, and a black 1930s evening coat, among many, many more.