Fresh off a family vacation in the Caribbean, Obama chose an oversize shearling jacket similar to styles the Barbadian favors on nights out, even sliding it off one shoulder as Rihanna likes to do. The wintry coat was offset by a fitted black crop top underneath, which flashed just the right hint of skin above her high-rise blue jeans—probably about as much as Michelle Obama would allow. As for accessories, a simple brown leather belt cinched the jeans and played off a utilitarian leather backpack, but it was Obama’s Timberland boots that gave off the strongest Rihanna vibes. The singer has been known to wear her own custom version and even drew inspiration from the iconic work boot when designing her second Manolo Blahnik shoe collection—but we think she’d also approve of Malia’s perfectly weather-worn pair.
/Vogue/
