Blogger and founder of The Man Repeller (manrepeller.com).
My Investment Piece: Derek Lam maxi dress, $3,190 (barneys.com for stores).
Why I've Gotta Have It: People think that outerwear should be their season investment when really, a maxi dress can go a long way literally and figuratively.
Hanging Out Look: A T-shirt tones down the dress's formal nature and makes it perfect for drinks with the girls.
Tips: A fun, chunky necklace and stacked arm-party adds a playful touch.
Keep a discreet hair band among your many bracelets for pulling up a messy bun whenever the mood strikes.
Tee, $54, Monrow at CPW; (212) 579-3737. Dannijo necklace and multilink cuff, Medine's own.