Hobos are great for casual ease, body-conforming fit, nonchalant daytime comfort, and maximum storage. The downside of all those enjoyable pluses: things go missing. The one item you need is always the one that’s impossible to locate as you fumble and rummage. Sissi Rossi has addressed it straight on with a roomy zip-pocket right within arm’s reach. The clever detail not only looks cool – it gives the large, seamed shoulder bag a snappy spot for your eyes to go, especially with their signature safety pin-style zipper pull (find a second pocket on the interior to keep every little thing in place).
A nonchalant look like this with that thick, one-piece double-sling handle will never fall out of fashion. And it’s a good thing too, distressed brown leather like this improves as it collects scratches from your loving wear. At Barneys New York for $935.
Pair with: See stars with a cozy sweater that flaunts an au courant pattern. In the classic combo of white and navy, Chinti and Parker’s take on cashmere brings prep to into your starry galaxy. On Net-a-Porter for $545.