An article of footwear includes an upper and a sole coupled to the upper. The article of footwear includes an inflation system. The inflation system includes an inflatable bladder, a pump in fluid communication with the bladder, and a control circuitry operatively linked to the pump. The pump adjusts the air pressure of the inflatable bladder. The control circuitry receives a command signal from a remote device, and upon receipt of the command signal, the control circuitry transmits an actuation signal to the pump to adjust the air pressure of the inflatable bladder.