The Chapman classic medium-sized waterproof duffle is on the pricier side of what we normally post, but it made our list for good reason. This UK-made overnight bag is worth it's weight in waterproof canvas. With genuine leather accents, a dual zipper design (allowing you to lock it closed) and brass feet give this bag a great look while maintaining a high level of functionality. Did we mention its waterproof? Because it is, waterproof cotton canvas mind you. You don't see a lot of these at your local J.Crew, which is probably why it holds a higher price tag. Caution: This is not a full weekender-sized bag, it is a tad smaller, so don't be disappointed when you can't fit 4 shirts, two pairs of jeans, and a sweater in here along with your chukkas. You've been warned.

Available at Bodenusa.com for $398