Dogs have been our best friends for the last 15,000 years. So it shouldn't be surprising that as soon as we invented the camera, we started taking wacky photos of dogs wearing glasses, hats, suits, ties and other gear. Here are the most adorable (and alarming) vintage photos of dogs wearing human clothing.

A real gentleman, c. 1900

(via vintag.es)

Tommy Atkins, c. 1905

(via Library of Congress)

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Old Heidelberg, c. 1905

(via Library of Congress)

An old sea dog, c. 1905

(via Library of Congress)

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The Missis, c. 1905

(via Library of Congress)

A fiddler dog by Harry Whittier Frees, 1914

(via Library of Congress)

Using sawhorse to saw wood, by Harry Whittier Frees, 1914

(via Library of Congress)

Watering the flowers, by Henry Whittier Frees, 1914

(via Library of Congress)

Making baby's clothes, by Henry Whittier Frees, 1914

(via Library of Congress)

A German Army dog from the First World War wearing a hat and glasses and carrying a pair of binoculars, 1916

(Photo by Henry Guttmann/Getty Images)

Smoking dog, 1923

(via Library of Congress)

Pep, the dog who was sentenced to life in prison in 1924

"Pep, The Cat-Murdering Dog was a black Labrador Retriever admitted to Eastern State Penitentiary on August 12, 1924. Prison folklore tells us that Pennsylvania Governor Gifford Pinchot used his executive powers to sentence Pep to Life Without Parole for killing his wife's cherished cat. Prison records support this story: Pep's inmate number (C-2559) is skipped in prison intake logs and inmate records. The Governor told a different story. He said Pep had been sent to Eastern to act as a mascot for the prisoners. He and the Warden, Herbert "Hard-Boiled" Smith, were friends. Pep was much loved, and lived among the inmates at Eastern State for about a decade. While the truth may never be known, in photographs Pep – with his head down and ears back – looks GUILTY" – according to the former American prison's own homepage.

(via Eastern State Penitentiary)

Smoking, 1926

(via janwillemsen)

Pete, the performing Staffordshire Bull terrier, in costume for his next role, 1927

(Photo by J. Eldee Hester/General Photographic Agency/Getty Images)

Jiggs II, bulldog given to Marines by Gene Tunney, in catcher's mask, on a photo taken by Leslie Jones in 1929

(via Boston Public Library)

A dog dressed up as a policeman and with a pipe in its mouth, 1929

(Photo by Fox Photos/Getty Images)

Sitting

(via Wall To Watch)

Dog with glasses playing the piano, photo by Leslie Jones, between 1934 and 1956

(via Boston Public Library)

Bulldog with hat, photo by Leslie Jones, between 1934 and 1956

(via Boston Public Library)

Dressed up, taken by Leslie Jones, between 1934 and 1956

(via Boston Public Library)

Tea Party, 1934

(Photo by Fox Photos/Getty Images)

Gangster dog in bowler hat, 1939

(Photo by Leslie Jones, via Boston Public Library)

A Dalmatian dressed up like a firefighter, photo by Leslie Jones, 1940s

(via Boston Public Library)

A boxer dog called Jefferson modelling a head scarf and glasses for an intellectual look, 1950

(Photo by Keystone Features/Getty Images)

Buddy, the Deaf Dog, late 1950s

(via The Hydrant Blog)

Under A Hairdrier

(via Joanne Casey)

Dogs, by Elliot Erwitt

(via vintag.es)