I’m fond of that kind of look, grunge (not too much!), and casual. Besides I feel that T-shirt dresses are the most comfortable dresses to wear and also very easy to adapt with the seasons. During winter time, wear it with Dr. Martens / military boots, and in summer time, wear it with a pair of flats or flip flops. You can find this type of dresses at Acne (for the New Yorker: I bought a great one in burgundy red, on sales at Barneys, $60) or at Zoe tees (France and UK).
Regarding the glasses, have a look on Culter and Gross website … (this is my favorite brand for glasses!) 🙂