An article of footwear comprising: a sole having a medial side, a lateral side, and a foot-receiving surface; wherein the foot-receiving surface has a forefoot portion, a heel portion, and a midfoot portion extending from the forefoot portion to the heel portion between the lateral side and the medial side; an upper having: a medial side portion extending from the medial side of the sole and tapering in width to a first distal end; a lateral side portion extending from the lateral side of the sole and tapering in width to a second distal end; a support member extending laterally at least partially across the foot-receiving surface at the midfoot portion and having a first end fixed to the first distal end of the medial side portion; wherein the medial side portion, the lateral side portion, and the support member are configured to wrap at least partially around a wearer's foot positioned on the foot-receiving surface and on the support member; a heel member extending from the heel portion of the sole; and a fastening system configured such that the first distal end is securable to the heel member posterior to the lateral side portion, and the second distal end is separately securable to the heel member posterior to the medial side portion when the medial side portion and the lateral side portion are wrapped at least partially around the foot. a sole having a medial side, a lateral side, and a foot-receiving surface; wherein the foot-receiving surface has a forefoot portion, a heel portion, and a midfoot portion extending from the forefoot portion to the heel portion between the lateral side and the medial side; an upper having: a medial side portion extending from the medial side of the sole and tapering in width to a first distal end; a lateral side portion extending from the lateral side of the sole and tapering in width to a second distal end; a support member extending laterally at least partially across the foot-receiving surface at the midfoot portion and having a first end fixed to the first distal end of the medial side portion; wherein the medial side portion, the lateral side portion, and the support member are configured to wrap at least partially around a wearer's foot positioned on the foot-receiving surface and on the support member; a heel member extending from the heel portion of the sole; and a fastening system configured such that the first distal end is securable to the heel member posterior to the lateral side portion, and the second distal end is separately securable to the heel member posterior to the medial side portion when the medial side portion and the lateral side portion are wrapped at least partially around the foot. a medial side portion extending from the medial side of the sole and tapering in width to a first distal end; a lateral side portion extending from the lateral side of the sole and tapering in width to a second distal end; a support member extending laterally at least partially across the foot-receiving surface at the midfoot portion and having a first end fixed to the first distal end of the medial side portion; wherein the medial side portion, the lateral side portion, and the support member are configured to wrap at least partially around a wearer's foot positioned on the foot-receiving surface and on the support member; a heel member extending from the heel portion of the sole; and a fastening system configured such that the first distal end is securable to the heel member posterior to the lateral side portion, and the second distal end is separately securable to the heel member posterior to the medial side portion when the medial side portion and the lateral side portion are wrapped at least partially around the foot.