Olukai

Kailua Shoe - Women's

At first glance, the Olukai Kailua Women's Shoe looks like a classic slip-on. At second glance, it looks like a boat shoe. At third glance, no one knows what it looks like anymore—the genre-bending blend of style, comfort, and class has fried many a shoe fanatic's brain. The rubber cupsole makes the Kailua look like a classic SoCal slip-on, but the full-grain leather upper gives it more upscale feel than most of the ska-kid kicks we grew up with. A lightweight canvas lining and removable EquiFit PU footbed makes it more comfortable, too, while the fold-down heel design means you can wear it as a full-fledged heelless slip-on if you don't want to mess with pulling it on and off.