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what to wear on the first day of college outfit #1 you could never go wrong with a tank top, denim shorts and a cardigan. Brandy Melville and Garage have the best tank tops. My favorite denim shorts are from Pacsun. And Old Navy has some great affordable cardigans. outfit #2 A matching set is the easiest way to look cute and put together. Brandy Melville has some really cute ones. And I love these comfy sets from Aritzia. outfit #3 If you want to look more elevated, then I would recommend a button-up top with either jeans or a mini skirt. Princess Polly is the cutest button-up tops. And Princess Polly also has built-in skirts. And I love these jeans from Pacsun. outfit #4 Another amazing outfit would be an athletic dress with sneakers. Here's a super cute and basic one from Garage. I also love this striped one from Altard State. And for shoes, I would recommend the New Balance 530s.