Returning from their well-earned 16-day getaway on Martha’s Vineyard, Massachusetts, yesterday, the First Family were like all of us: slowly coming to grips with the summer’s inevitable end. But Michelle Obama was still clinging to the last days of the season. In an empire-waist black-and-white checkered frock and black cat-eye sunglasses, the First Lady showed no signs of breaking out any new fall purchases just yet—save for a pair of squeaky-clean Converse Chuck Taylors. The all-American staple added a sporty edge to her prim summertime look, and was a styling move we hadn’t quite seen the fashion chameleon try before. Perhaps she was taking cues from her daughter Malia who was also laced up into a pair of Converse high-tops while wearing a white shirtdress. The First Daughter and Lady were having the definitive end-of-summer preppy cool mommy-and-me moment.
In fact, it would be Sasha in her flatform wooden sandals and black peasant dress who broke with the family dress code. The look was a far cry from the uniform the teen had been donning at her summer job, and was a stylish reminder that there are plenty of warm-weather looks to be worn, and still plenty of time in which to wear them.