Check out the Glassy Eyes blog here: http://glassyeyes.blogspot.com
There are several places you can order glasses online and afford to get several pair and still spend less than you would for a single pair at a chain store or anywhere else. Glassy Eyes has reviews for some of the bigger places.
I’ve bought eight pair of glasses online now! Admittedly, many of the glasses from these online places aren’t the best looking (some are just plain weird), but there certainly are some nice ones. I’ve been making all my purchases through one site so far (Zenni Optical), and I’m really happy with all of the glasses I’ve bought. (Okay, I returned two pair, but only because I got a little too adventurous in my selections, and those two styles looked, for lack of a better description, out of place on me. But the other eight are great!) I haven’t had any problems with this company, and I plan on going back to try ordering some prescription sunglasses. My first order cost me just under $42 for three pairs of glasses *and* shipping!
Your coloring and face shape is pretty similar to mine, and I think you’ll find you can pull off a pretty good variety of styles/colors. If you don’t want to obscure your eyes, I’d recommend a rimless style or a half rim frame, most of which are metal, that isn’t too heavy looking. I have metal allergies so I’m partial to plastic frames. I don’t wear a lot of jewelry (again with the allergies!) so my glasses are my big accessory. I actually bought a pair of red plastic frames ($8 with lenses!), and they really pop against my light skin and dark hair and draw attention to my eyes. They’re very similar to the ones in this picture, which actually inspired me to try the red ones in the first place. Like Angela suggested, tortoise or dark plastic frames will probably look great on you! I have these tortoise frames. They’re not so stunning in the stock pic, but they look great on and get me compliments all the time. The other day I had someone tell me I should be an eyeglass model. Strange but true! Probably the best $19 I’ve ever spent.
If you decide to try ordering online, I recommend going somewhere to try on different styles first so you can figure out what shapes and colors you like best and then try to find similar ones online. Other than that, all you need is your full prescription and the distance between your pupils (your optometrist should have this on file anyway from the last time you bought glasses), and you’re good to go.
Whew! Long post! If you have any questions or anything, I’d be more than happy to help!