What flatters you

Now that I've expressed a bit of a carte blanche attitude about what vintage one could and should wear, I need to take one step back. I do believe you can wear what you feel good in, but you may feel better (and look better) in some vintage styles more than others. It is good to cultivate a sense of what flatters you.

Because “vintage clothing” has been defined as any garment twenty years old or older, you have a pretty big range to choose from!

Do you know what your best features are? Consider not just your figure, but your face, your hair, your neck, your ankles, your shoulders...heck, even your knees. There is an era and a style that is going to show off your best. In a general sense, the 20s and 60s favor a straighter, younger, thinner shape, while the late 40s through the early 60s was the hourglass era. I consider 1939-46 a somewhat more natural (neither straight nor exaggeratedly curvy) era, same with most of the 70s.

Take a look again at some styles I've shown from the 20s through the 80s:

ca. 1925

ca. 1930

ca. 1935

ca. 1940

ca. 1945

ca. 1948

ca. 1950

ca. 1955

ca. 1960

ca. 1965

ca. 1970

ca. 1974

ca. 1978

ca. 1985

ca. 1990

There are many more silhouettes from these eras, this is just a very general sense. Many more silhouettes and garment types are covered on fashion-era.com. This site contains an absolute gold-mine of information. I check this great reference often to help confirm my dating of items. Another great reference is the Vintage Fashion Guild's Fashion Time Line. Look for styles or components of styles that will help show you at your best. Many people tell me that they love such-and-such an era and that is all that interests them. If that is your case, you may limit yourself somewhat. I recommend staying open-minded.
One caveat: Before I get anyone too excited about very vintage and antique (defined as 100+ years old) clothing, let me caution you: Rare and delicate items need to be treated with respect and care, and may not actually stand up to wearable use. A great example of this, particularly because popular culture is currently mad for it: 1920s beaded silk dresses. These gorgeous creations are everything good except durable. The weight of the beading, sequins, and/or metallic threads applied to fine silk has just not stood the test of time in many cases. If you find such a dress in wearable condition, you should seriously consider (and I know this hurts) not wearing it, or just wearing it briefly for a photo. Clothing is in fact ephemeral. 
Next time: Alternatives to authentic vintage items