We love how our friend Cynthia paired a wedge Chukka boot with baggy chinos (nicely peg-rolled) . The wedge makes the chukka a little more feminine and less casual. We think they’d look great as well with skinny jeans. She got hers at L.L. Bean for a song, before they sold out in every single size and color. Despite late night phone calls to the incredibly nice customer service representatives at L.L. Bean, they will not be reordering this season. For a similar look, we like these slightly higher wedges from Toms, Tory Burch, and J Crew.