Oversized turtleneck: Worn either as a top or as a minidress, this cozy oversized knit can do double duty. The draping on the side adds a subtle punch to this winter basic.

Stephanie Strauss, Assistant Market Editor

Hitched up skirt: Paired either with pumps or flats, this navy blue, multilayered draped skirt is easy, nonchalant elegance.

Melissa Karl, Assistant Accessories Editor.

Oversized trousers: Consider these a posh alternative to your basic sweats. Draped and fluid with darts at the hips and roomy cut legs, these deconstructed tuxedo trousers can transition from a day at the office to black tie.

Trompe l'oeil high-top: Clean, slick, and functional, these sneaks, in winter white with a caramel rubber sole, are perfect for casual day-to-day activities.

Invisible wedge ankle boot (black): There's not much about Lucite that we don't like, and with a slick geometric wedge matched with a black leather upper, these ankle booties are, quite literally, like walking on air—a 21st century take on space-age.

Jessica Mycock, Senior Fashion and Accessories Editor

Open clasp watch: MMM is synonymous with no-nonsense but inventive utilitarian jewelry, and this bracelet, modeled on a watch, is a clever, surreal update on the classic ID bracelet.

Darted Sweater: A high neck for winter, with some fashionista flair.

Charlotte Fetridge, Fashion Assistant

Watch Braclet: Telling time is overrated. We love the balance of feminine and sexy bondage the ribbon gives this bracelet.

Miguel Enamorado, Fashion Director

Two Jackets: Simple, chic, necessary.

Reversed Denim: To wear with our new blazer, of course!