French Connection Hat
Topped with a pom-pom, this acrylic-blend cap is a cheerful essential.
To buy: $20, frenchconnection.com.
The genius of a navy tweed topcoat? It classes up anything you wear underneath.
To buy: $99, hm.com for stores.
Rachel Rachel Roy Top
Embrace your feminine side without leaving your comfort zone, thanks to this polyester-blend sweatshirt with silk panels and an open back.
To buy: $59, rachelroy.com.
Stretchy black corduroys feel like leggings but look more put-together.
To buy: $39, hue.com.
Lucky Brand Flats
Tread brightly with faux-suede slip-ons.
To buy: $48, zappos.com.