Use of stamps began on 8 May 1858, with stamps of Great Britain.
Until 1860, the postal service under the control of Great Britain, despite repeated efforts by Jamaican authorities to take over. Soon afterwards, British stamps were no longer accepted, and De La Rue was commissioned to produce stamps for Jamaica, featuring a laureated profile of Queen Victoria. The first issue consisted of five values ranging from one penny to one shilling, each with a different frame, inscribed "JAMAICA POSTAGE", and were watermarked with a pineapple design. They were first issued on 23 November 1860. Additional stamps in the series appeared through the end of the century.
In 1863 four letter boxes were placed around Kingston. Inland delivery was increased from twice/week to three times per week in 1868. Mail carriage was originally via mule, then via railroad in the 1860s, then back to roads due to difficulties with the trains, not switching back to railroad until the railways were improved in the late 1870s.
Jamaica joined the Universal Postal Union on 1 April 1877.
In 1887, the Legislative Council resolved to use a common stamp design for both postage and revenue purposes, and in 1889 Jamaica issued three key plate stamps inscribed "POSTAGE & REVENUE", with the value tablet in a different color.
In 1900, Jamaica's first pictorial stamp featured a view of Llandovery Falls. Originally intended as a commemorative stamp marking the adoption of Imperial Penny Postage in 1889, it was too long delayed, and is considered a regular stamp. Originally issued in red, it was redesigned and issued in red&black the next year.
For unknown reasons, Jamaica did not adopt a profile of Edward VII upon his accession. Instead, beginning in 1903, new stamps featured the coat of arms of the colony. Following a special petition in 1910, Edward VII was recognized posthumously on a two-pence gray stamp issued 3 February 1911. Stamps depicting George V were more timely, first appearing in 1912.
A pictorial series in 1919 included twelve stamps, ranging from the Jamaica Exhibition of 1891 to various statues and scenery. The series was not commemorative, but was a result of repeated requests by local philatelists to governor Leslie Probyn.
The next definitive series was issued for George VI in 1938, with low values being a profile of the king alone, and the higher values including scenes of various local industries. An issue with new scenes and a full-face portrait of George VI marked the granting of self-government in 1944, although it was not issued until August 1945.
A set of four stamps with historic scenes marked the 300th anniversary of British control in 1955, followed in 1956 by a series of 16 stamps depicting flora, fauna, and local scenery.
Upon independence in 1962, the 1956 stamps were overprinted "INDEPENDENCE" and "1962". In 1964, a set of three depicted Miss World Carole Joan Crawford; they were soon followed by a new series of 16 with various designs. Only the one-pound value included a portrait of Queen Elizabeth; from independence on, the Queen was rarely included in designs.
(Information from wikipedia.com)