With the large amount of high waisted, cut off shorts you probably bought over the summer, it probably seems like a waste to stuff them in the back of your closet where your other seasonal clothes (think obnoxious Christmas sweaters and nauseatingly pastel Easter dresses) go to die.
Cue the thigh/knee high sock.
Thigh/knee highs have been one of my go to summer-to-fall transitioning staples for almost 5 years now. Nothing says "I really like this outfit but I am aware it's 3 degrees Fahrenheit outside right now and I could easily get hypothermia and frostbite if I don't cover my extremities" more than a pair of your favorite shorts worn with some thigh highs.
The pairing of a delicate top with a relaxed, cropped sweatshirt definitely gives me a Cher Horowitz vibe (it is a life long dream of mine to create that white button up shirt under a sweater vest look). I found the cropped sweatshirt in the boys department at a local thrift store. My friend looked at me like I was insane when I squealed with delight. Who's the crazy one now? (probably still me).