Our friends over at Killspencer have updated their Weekender bag with handy features and high-quality upgrades that put this bag near the top of our list of best classic duffel bags. Whether you are flying on a business trip or taking a weekend off in the country, a weekender bag is the perfect size for, you guessed it, a weekend’s worth of clothes and necessities. While worn-in, slouchy styles may suit some tastes, this Original Wax Weekender 2.0 ($375) bag from Killspencer has a structured design that brings some polish and sophistication to an old standby. Upgrades to the original design include a waterproof interior pocket, expandable open-top design, and a zip-pocket for your MacBook Air or iPad. The bag also features two exterior pockets, a bullhide leather handle, and water-resistant AquaZip zippers to keep your things nice and dry. We like the Original Wax black fabric for its clean lines, but the bag is also available in three other finishes, including Olive Drab and Korean War Era canvas.