Penny Pleated Bow Heel

When Jesse Randall couldn’t find shoes that she was truly excited about, she went ahead and did what any savvy designer would do: she fashioned her own. In 2004, she teamed up with her husband to launch Loeffler Randall, an ebullient line of bags and shoes that are at once playful and polished. Today, the brand still manages to hit that sartorial sweet spot, offering up everything from animal print bucket hats to sophisticated combat boots.