Best Bet: Mini Mailbag

When you're toting winter gear, gadgets, and subway reading, a tiny crossbody bag won't cut it. Madewell’s new mini mailbag, available in blush pink, tan, and classic black, is a happy medium between clutch and canvas tote. The boxy, vintage-inspired shape is refreshingly unadorned, and it makes a versatile transitional bag for schlepping your iPad or Kindle. For a similar look, it's less expensive than a Cambridge satchel.

Mini mailbag, $118 at Madewell or online.