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A deerstalker (right) along with typically associated paraphenailia of Sherlock Holmes

A deerstalker is a type of hat that is typically worn in rural areas, often for hunting. Because of the hat's popular association with Sherlock Holmes, it is also a stereotypical hat of a detective.

Its main feature is a pair of fore and aft brims and two flexible side flaps. The dual brims provide sun protection for the face and neck of the wearer. The side flaps can be worn down or tied under the chin to protect the ears in cold weather, or tied up above the crown to keep them out of the way when not in use. The checkered pattern in the twill fabric also serves as camouflage, and modern hunting clothes (including deerstalkers) are often made with a red-and-black or orange-and-black check pattern for this and hunter safety.

The most famous wearer of this kind of hat is the fictional character Sherlock Holmes, who is popularly depicted favoring this style of hat. However, in Arthur Conan Doyle's stories Holmes is never actually described as wearing a deerstalker. The public perception of Holmes as a "deerstalker man" was derived from the original illustrations for the stories by Sidney Paget, Frederic Dorr Steele and others. Later uninformed depictions of Holmes wearing this hat in the city fail to take into account that the fashion-conscious Holmes would never commit such a faux pas; the deerstalker is traditionally a rural outdoorsman's cap, not the appropriate headgear for the properly-dressed urban gentleman. Paget and the other illustrators who portrayed Holmes in a deerstalker always placed him in the proper setting for such attire (i.e., traveling crosscountry or operating in a rural outdoor setting).

Legendary 60's British R & B band, The Downliners Sect, also shared an affinity for the Deerstalker cap, so much so that it became a trademark for most of their publicity photos and album art work.