If you're looking for the absolute most reliable place to sink those wardrobe dollars, a classic carryall's your best bet. Whether you opt for a classic flap-front 2.55 shoulder bag, a quilted tote or even a tiny crossbody carryall, there's just no going wrong with anything double-C-adorned. Proenza Schouler's cult-forming PS1, meanwhile, has made the tricky transition from trend to cool classic with ease. And of course, few can resist the heritage-steeped house of Hermès. While Birkins and Kellys may yield the longest waitlists, we're currently smitten with the smaller Constance crossbody.