Hey Delilah, I've been doing vintage/pinup hair for a few years now, and I can tell you that all it takes is learning the techniques and some practice!
Resources (you're going to have to work with me since I don't have enough posts yet to link URLs!)
The Fedora Lounge (thefedoralounge.com), specifically this thread that I started to round up some great tutorials for the members, as they were spread all over the place: thefedoralounge.com/showthread.php?56507-The-Hair-Tutorials-thread
And another awesome one is Lisa Freemont Street, she does a lot of great YouTube tutorials.
I hope that helps you π
I love the pin up style I've just started growing my hair again so I can start wearing my hair all pin up XD
I got a book by Lauren Rennells called Vintage Hairstyling and i just love it. it shows + explains step by step what to do. It was almost $40 though but i finally got it earlier this year