Dolce Vita Jody Skirt, $132 at shopbop.com, Elegantly Waisted Addison Belt, $96 at shopbop.com, Prada Multi-Strap Pumps, $695 at neimanmarcus.com: First off, the pants have to go. The top is vastly unflattering and a lot of look on its own, so it needs to be paired with a simple, sleek skirt. The extra skin exposed helps balance out the bulky upper half nicely. I'd go for black accessories, so they don't compete with the top and make the overall look too busy, but black with some sort of interesting detail to keep the feeling young. A slightly narrower belt would be more flattering and much more chic. I like this Elegantly Waisted belt because it's elastic in the belt, so it'll blend right into the skirt, and the black on black studs in the front draw the eye to the waist without being too attention-catching. I'd finish it all off with these Prada peep-toe pumps. Since they're basic black, they don't steal the show, but the big platform and all those tiny straps add a very necessary bit of edge, taking this look from slightly matronly to fashion forward.

Image Sources:
Leighton Meester, in order: gofugyourself.com, glamour.com, Dolce Vita skirt: shopbop.com, Elegantly Waisted belt: shopbop.com, Prada pumps: neimanmarcus.com
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