The skull with wings logo is used extensively in motorcycle club/gang art. In the early 1930s, motorcycle riders started to develop a kind of modern-day outlaw reputation, inheriting some of the heritage of the outlaw pirates of the past. Harley Davidson played to this image and capitalized on it by introducing a skull with wings logo. Later, chapters of the Hells Angels motorcycle club often featured a winged skull on their jacket logos.
The skull with wings motif also has a long history of military use. The first combat mission with B-25 bombers bearing the now famous “Skull and Wings” insignia, was flown on 18 February 1943, but symbol is actually much older than the 20th Century.
Through time there is a close connection between the skull with crossbones symbol and the skull with wings symbol. A skull is representative of the transitory nature of life and death, or sometimes the death-resurrection cycle. Sometimes skulls are shown with wings, called death’s heads or winged death, symbolizing the fleeting nature of life and death. Alternatively, skulls are shown with crossed bones beneath, representing death and the crucifixion.
Both the skull with crossbones and the skull with wings icons were popular symbols in America in the 17th and early 18th centuries, particularly on grave headstones. Here the winged skull symbolized the flight of the soul from mortal man. During this time the skull and crossbones image was popular both on headstones and the flags of seafaring pirates, inspired by gravestone images, meaning, you are about to die.
Going back before the 16th century to the Middle Ages, the skull and crossbones symbol is also used in initiation rituals as a symbol of rebirth. In Kabbalistic rituals, it symbolized the gateway to the higher realms of understanding only achievable through spiritual death and rebirth. In this context a skull did not inspire horror; it symbolized the promise of a new life. In Astrology the skull simply symbolizes change.
It seems the common thread here for the meaning of the winged skull is the link to death. However, throughout time the meaning has not been absolute death, but rather an emphasis on a spirit transitioning between planes of existence or heaven and earth.
Historian, Harley Owners Club, Kingwood, Texas Chapter
Carlos Miller, The Arizona Republic
Gerald Erichsen, About.com