It's worth it to spend money on outerwear. A pop of color or a unique shape in a jacket can change your entire look. Zara has great jackets for less, Tibi jackets are adorable and chic, and Celine has amazing jackets at a designer price point.
Jacket: Ali Ro. Jeans: JBrand. Scarf: Lilly Pulitzer. Boots: Hunter. Sunglasses: Ray-Ban. Earrings: Anthropologie. Watch: Michele. Bracelet: JCrew.