Nothing feels more like Fall to me than swapping fresh florals for school-inspired plaid prints. In classic shades, or this season's brighter yellow versions, the effect is prep-school-meets-fashion-girl. While booties in any colour work well here, a fresh pair of white kicks gives your basics a 2018 spin.
On Hannah: Zara top, Citizens of Humanity jeans (shop similar, Tibi boots (shop similar, Balenciaga bag, Westward Leaning sunglasses (shop similar)