Don't underestimate the ability of your favourite accessories to give basics a boost. Start simply with a striped tee, denim jacket, and jeans. Add in a bold cross body bag, heels, and your favourite earrings — et voila! — your outfit goes from everyday to infinitely more attention-grabbing, albeit without trying too hard.
On Hannah: Madewell jacket, POPSUGAR at Kohl's collection shirt ($36), Madewell jeans ($128), Ganni bag ($395), Manolo Blahnik heels ($1,055), J.Crew earrings