Aside from family members, old movies and television shows, most people I know today don't really have a reliable or complete source of knowledge when it comes to vintage fashion and how to put together certain types of clothes.
I get asked all the time what sources do I derived my knowledge for wearing vintage attire and for me, my biggest go to place when I really want to investigate different types of clothing, outfits, or just the purpose of a particular piece is books.
I make a point every few months to scour Amazon to find any dated books on just exactly how people put their outfits together back in the day. Out of the many books I have, one series in particular is a plethora of knowledge and pictures for you to not only drool over but really understand just exactly how these clothes are meant to be worn. That source is the "Fashionable Clothing From The Sears Catalog" series by Tina Skinner, which covers from the 1920's-1980's. This is my favorite resource because these books are truly thorough in covering all aspects of fashion rather than having just two or three pictures of this or that but provides a multitude of pages covering any and everything that you would see in a modern day Sears catalog.
Not only does this series cover so many decades but it actually covers the early, mid, and late periods of each decade for both men and women so you can get an idea of just exactly how to date your clothing as well as understand how fashion evolved over the years.
I really love the layout of these books because not only do they give you detailed pictures of the clothing but they show you exactly how the layouts appeared during those times, not the mention the cheap prices that you wish you could still get these clothes for - *SIGH*
These books are also great because they even go as far as to cover shoes, lingerie, sportswear, lounge wear, and more so you can really understand how fashion played out in everyday life.
So if you haven't seen these books yet, definitely check them all out on Amazon as they have really helped me learn how to organize and put together outfits down to the minute detail when no other resource was available.
Hopefully these books will not only help give you some ideas on how to put your wardrobe together but provide inspiration for creating your own vintage look as well!