I was asked via email for my advise on getting past the intimidation of vintage stores and what I typically look for when shopping. Here's what my quick response turned into. It may not be beautifully written but I sure enjoyed writing it...
Yeah they can definitely be overwhelming!
I find it helpful to walk into places knowing the types of things I like/need and are easy to add to my existing wardrobe and home decor.
If you aren't looking for anything specific then just go when you have the energy and time to simply browse. There's nothing worse than feeling tired or crunched for time in a vintage store. There's simply TOO much to look at but also know that its OKAY to not see everything. I fly past the ceramics and toys because I know I'm not interested. Things related to fashion and home decor stop me in my tracks.
If you like fashion accessories, necklaces, purses, scarves and handbags are great to start out with. Most of what's out in stores today is based on old styles so it's always fun to get the original thing. They are often of better quality too. Accessories may help you feel like you can "pull them off" because they are so easy to mix into what you already have.
I would avoid getting into clothing until you feel more comfortable sifting through alot of "stuff". Many vintage clothing items require alterations and understanding of fabrics and construction (to scout the real winners for quality and comfort at least) so that may be too much for starters.
My hunch is that this may also be the stuff you feel like you cant pull off? Vintage clothes can be intimidating but if it's priced well for you, think about how it can be incorporated into your everyday wear (or special occasions) seamlessly rather than trying to convince yourself that you will wear it. Just because it's trendy and looks like the latest designer styles doesnt mean it's worth buying, especially if its not "you" already. You wont ever wear it or pull it off if it doesn't feel right to begin with.
What I've been shopping for lately have been items for the home since I just moved too. I make a mental list of what I need/want so that everytime I step into a shop, those things catch my eye immediately amidst all the clutter. For example, I needed a small portable table mirror so that I could do my makeup by my window. I found an amazing metal one within two minutes of going through a store, and for 6 bucks!
Think of it as a treasure hunt for something unique and it will become like a game. Just take the first step inside and see how you feel...your eyes will lead the way :)