When you're going away for just a weekend (or a 48-hour business trip), you don't want to be the jackass lugging along a giant, rolly suitcase. Showing up with a giant suitcase for a short trip says, "Hi, I'm high maintenence." What the hell do you need to pack, anyway? You need two outfits, your toiletries, and your iPad. Case closed.
This Savile Weekender Bag ($389, Monte & Coe) is all you need. Named after London's historic, fashionable Savile Row, the bag is made of gray felt with brown leather straps, meaning it's fancy enough for a business trip and casual enough for a weekend with your buddies.