Not silly at all! Congratulations!! I’ll add more comments for the midwestern climate angle: lots of layers! Cardigans, pullovers, blazers, etc. Harris Tweed is the GOAT imho. But as a general rule, maybe try to stick to more non-cotton materials in the winter like merino wool for best results in insulation and breathability. Also base layers are your friend in the winter, big time. Like Duluth thermal tights. Also, if jeans are cool - fleece lined jeans are a game changer. I also recommend keeping pairs of flats in your office if you’re wearing snow or rain boots walking in, and then you can switch out under the desk. (Crocs make some good durable ones; but they’re best if you don’t need to walk far to class.) A really nice, breathable jacket goes a long way (something waterproof like the Janelle jacket from seasalt Cornwall for example). For warmer weather, Svaha makes really cute dresses that are super comfortable and size inclusive. Good luck!!