Glance at this bag head-on and it looks like a typical satchel reminiscent of a doctor’s bag. Stare a moment longer – and you probably would – and you’re struck by the side pockets that flair out, for a cool shape and interesting profile. These pocket protrusions break up that super-structured body and make Michael Kors‘ ladylike bag just a tad rebellious.
The wide opening does have a downside and that’s in the closure. You have to be okay with leaving it open most of the time; the zipper comes apart completely, so in order to close it you have to attach the zippers, for a tricky open-and-shut. It’s often the more conservative-looking bags that require the easy-going owners! It comes in two colors, “elephant” and “teak,” but the almost metallic “elephant” gray grants the silhouette way more depth – and it’s radically more youthful than its brunette counterpart. At Saks Fifth Avenue for $795.
Pair with: A deceptively classic shoe, like Alexandre Birman’s python pump with built-in platform and a toe that strikes the balance between pointy and round. Alexandre Birman Python Platform Pump, $550.