The Best Gucci Bags of All Time

If you didn’t know already, the Jackie bag gets its name from former First Lady Jackie Onassis Kennedy, who was photographed in 1961 using the shoulder bag (originally called Fifties Constance) as a shield against paparazzi. While just as popular today, the Jackie bag is so much more than its start-studded association. Its strong calfskin leather and canvas design make it a very favorite Gucci silhouette—which you can read all about in our best designer bags write-up.

The medium web stripe-trimmed coated-canvas bag might be the most recognizable iteration, but the label has expanded into various sizes and hues, including pared-back pink and blue pastels that, according to our co-founder Stefy Allen, are a favorite of our private clients. For Naer, it’s all about the Grace Kelly-inspired floral design, which she purchased second-hand after seeing a handful of Scandinavian it-girls sporting the silhouette. “Everyone in New York and Copenhagen is styling it with different basics and blazers. It kind of adds this special pop-effect to an outfit,” says Naer.

For your first Gucci bag, we recommend sticking with the classic web-trimmed coated canvas silhouette. Playful patterns and colors require more styling forethought (pro-tip: stick with neutrals). An added bonus: the archival GG-coated canvas only looks better as it becomes more worn. Plus, the medium size is big enough to fit a 13-inch Macbook, your phone, and those all-important designer sunglasses. If you want the vintage look straightaway, check out Vestiaire Collective and Rebag. Aside from its ’60s appearance, what we love most about the Jackie bag is that it’s easy to use. Other shoulder bags like Saint Laurent Manhattan take time to get used to due to the intricate fastening, but the signature piston-lock closure is seamless to open and close, making for that smooth, sleek user experience that we crave in all our luxury goods.