I don’t typically head to Gap for much of anything these days, but I do really like the brand’s Leather Satchel. It’s a study in simplicity, made of smooth leather (in your choice of gray, beige or this navy) and accented by a tan strap and handles. A soft slouch gives it a casual feel without taking away from its pulled together look. A great choice if you’re in the market for a neutral, timeless handbag. Available for $100 at Gap.