J. Crew Horsing Around Sweatshirt (also here), Clare Vivier Haircalf Clutch, Current/Elliott boyfriend jeans, Samantha Wills bracelets (c/o), Urban Outfitters button down, Nine West heels (c/o)
Hard to get cozier than boyfriend jeans and a sweatshirt. Now, comfy shapes like this can get muy messy, muy rapido. But the prancing, fancy-pantsy horse motif does help counteract the slouchy effect (far more prepster than hipster), and a good pair of pumps can elevate any outfit.