We have always been enamored with the classic, effortless, yet incredibly chic style of Caroline Bessette Kennedy. She stuck to figure flattering pieces in black and neutral tones with a splash of color or print here and there, and the occasional polished red lip. Clean, simple and stunning.

Shop the Classic Caroline look: The Jessica by Haney - Alexander McQueen Pencil Dress - Reed Krakoff Sandals - American Vintage Black Top - Burberry Pencil Skirt - J. Crew Button Up - Current Elliott Boyfriend Jeans - Thierry Lasry Sunglasses - NARS Lipstick - Miu Miu Leopard Purse - Meandher Valentina Loafer