Ann Demeulemeester Sandals, $689
Every season I fall in love with a pair of Ann D’s. They’re understated, but still a little edgy, and to top it off, they look so comfortable. This is a less obvious choice, because even though the designer is legendary, she’s not as trendy, and is less known outside of fashion circles. If I were fortunate enough to have a pair of these, I would wear them everyday. With everything.