The name Oakley has its origins in Old English and is derived from the words "ac" meaning oak and "leah" meaning meadow or clearing. It was originally a surname referring to someone who lived near an oak tree clearing or meadow.

The earliest recorded use of Oakley as a given name dates back to the 13th century in England. It was initially more common as a surname, but gradually transitioned into use as a masculine given name over the centuries.

One of the earliest known bearers of the name Oakley was Sir Thomas Oakley, an English landowner and knight who lived in the 14th century. Another notable person was Walter Oakley, a 16th century English merchant and explorer who traveled to the West Indies.

In the 17th century, Oakley Charnock was a prominent British naval officer who served in the Anglo-Dutch Wars. He was born in 1632 and died in 1687.

Moving into the 18th century, Oakley Hamilton was a British colonial administrator who served as the 12th President of the Council of New Jersey from 1738 to 1743.

In the 19th century, Oakley Hunter was an American politician who served as a United States Representative from Ohio between 1835 and 1837.

While traditionally a masculine name, Oakley has also been adopted as a unisex name in more recent times. One notable female bearer of the name was Oakley Browne, an Australian novelist and short story writer who lived from 1914 to 2003.

Throughout its history, the name Oakley has maintained its connection to the natural world, particularly oak trees and meadows. Its roots in Old English reflect the significance of these elements in the lives of early English communities.