Style Analysis: Classically Edgy

This style analysis is based on a friend of mine from my old middle school. We were locker neighbors in seventh, and had a couple classes together in eighth. Throughout all of that she was always cool, funny, and insanely stylish. She looked good even in seventh grade, and no one looked good in seventh grade. Her style veered from a classic hipster to a punked out retro thing. She would take inspiration from Audrey Hepburn and wear black capris with a t-shirt but wear dark burgundy lipstick with her wild curly hair. She is cool. Here are some of the things she wore most.
Classic black skirt- just at the knee. Her style was a 1950s rebel and she almost always kept modesty at the forefront of what she wore.( these images are from her Pinterest)

 Plenty of t-shirts- she would wear nerdy t-shirts, band t-shirts, plain black t-shirts- it all fit perfectly with her skirt, jeans, or whatever she wore. Not super baggy sports shirts, but slightly fitted soft vintage (or not) shirts that represent something you actually love

Converse- Go to. Whether worn by 12 year old boys from the 50s or hip twentysomethings now, converse have transcended time and will eternally look simultaneously cool and sort of outsiderish. Classic black, red, or burgundy would do nicely here.