Okay. Here is my area of experties. Try something comfortable like sweatpants, looose tee-shirt, jacket and Uggs. But there is always more options.
Where I live American Eagle, Aeropostale, Abercrombie & Fitch, and Hollister is the cool clothes to wear. I wear them there really cute and comfortable. They sometimes can be pricey. But if you get them when there on sale, its soo worth it. Make sure to get Fashion Tops and Cardigans. There a must when you want to dress up a little. Make sure o get a pair of each jean type. Super skny, skinny, bootcut, Flare, and jegging. just in case. Try to get a pair of clogs from American Eagle. Uggs are a must or a pair of Boots from Aeropostale. Hoodies too. I like these clothes mostly because there very simple yet dressy. They may seem expensive but there good quality. A fleece The North Face Jacket is a favorite of many. They keep you very warm. Addidas is good if you play sports as well as Under Aurmour. If you can't afford these or don't like these try WetSeal, Forever21 or JcPenneys. Hope this helps.
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This depends mainly on the season, trends and school dress code. I would look around what people at school are wearing take the general idea and make it your won. If you don't like it then try current trends and styles. If you don't like any of it then, i would try classics: cardigans, blazers, button downs, jeans, t-shirts, sneakers and things like that. Always stay true to your personal style.