You have to be living under a rock to not be aware of the trend of the “hipster” glasses. These are big framed black (or other colored) glasses that are more than likely worn for style purposes. The glasses help create a vintage feel to a persons outfit, obviously since these type of shaped glasses were worn back in the day, you may catch your grandparents still wearing these type of frames! Well, like everything that was worn in the past, mostly everything will make its comeback to future generations like these have.
I know I have personally felt intimated by these because I was unsure how to style and wear them. Felt awkward at first, but once you get the hang of them and awkwardly wear them out a few times, it will come together and you will notice you can almost pair these up with anything to give a different feel to your outfit.
Make-up wise, I would avoid any bright shadow colors or anything too complex. I think simple liner and highlights would do the trick to keep it simple and vintage inspired, rather than have a whole eyeshadow look that people wont even be able to noticed behind the frames anyway. Make sure to keep the ridge of your nose well powdered because often glasses start slipping around the area where they lay and can rub your foundation off. This is the look I wore with mine.
On my eyes I am wearing Nylon by MAC to highlight the inner corners and a no-name brand of brown gel liner. I coated my lashes with Voluminous by Loreal. On my lips I am wearing Blankety by MAC and cheeks Harmony, also by MAC.
An outfit example would be a black leather jacket over a loose white wife-beater with some distressed jean shorts and combat boots paired with these type of glasses. The looks these could go with are endless!