It’s rare that I feature a Burberry bag. I’m not a fan of plaid bags in general, however, every now and then, I will find one that catches my eye. The Burberry Check Chain Medium Weatherby Hobo didn’t make it on my wishlist but I would totally recommend it. The coated canvas and creamy, neutral leather trim with the chain and lock details gives an unexpected edgy twist to the classic Burberry check pattern. Price: $1,095 at Bloomingdales.com.