She’s wearing the J. Crew men’s super-soft cotton button-down in an xs.

The bubble shape of the skirt saves this outfit from being too literally a school uniform.

She loves how versatile her LD Tuttle boots are – perfect with skirts or pants.

Brighten up all these classic neutrals with a cheery cashmere scarf.

A shrunken cardigan won’t cover the cute shape of this skirt.

Sam borowed my Il Bisonte bag for the shoot – she’s constantly sending hotel guests to the store on Sullivan Street.

“They make me happy when I look down!” she says of her hot pink socks.

.