A headwear support system includes a support base having a shape that is generally one-half of a hemisphere. The support base includes a front projection extending outwardly therefrom, a rear connection rib coupled to a top rear of the support base, and two diametrically-opposed apertures on a bottom rear of the support base. The headwear support system further includes a first elastic member having opposed ends, each end configured to be coupled to respective ones of the diametrically-opposed apertures and wherein the first elastic member is configured to selectively secure the headwear to the support base. The headwear support system also includes a second elastic member configured to be coupled to the rear connection rib and configured to be selectively coupled to a button of the headwear. A clip member is also included in the system and is configured to be coupled to the rear connection rib and configured to be selectively coupled to a travelling case.