With the vicious baggage fees and shrinking personal space on planes these days, the benefits of a tailored yet tough weekender bag shouldn't be ignored. But when the open road calls, how do you answer it? Do you simply need a vessel in which to toss your clothes and toothbrush? Perhaps you require a bag engineered for the modern business traveler. Or maybe you want a beautifully tanned leather carryall—the kind Ralph Lauren packs when he heads to his Colorado ranch. However you choose, it's clear that when it comes to weekender bags, what you're carrying says as much about you as what you're packing inside.