Sandals with adjustable post assemblies are disclosed herein. In one embodiment, a sandal can include a sole assembly and a first strap coupled to the sole assembly. The first strap is positioned to engage a forefoot area of a wearer's foot. The first strap includes an aperture proximate to an intermediate portion of the first strap. The sandal also includes an adjustable post assembly extending through the aperture. The post assembly includes a post portion coupled to the sole assembly and one or more flexible second straps projecting from the post portion and configured to be releasably coupled to the first strap. The first strap is movable along at least one of the post portion and the one or more flexible second straps to adjust the position of the first strap relative to the sole assembly for engagement with the wearer's foot.