Bailey developed a love of natural history, and this led him into photography. Suffering from undiagnosed dyslexia, he experienced problems at school. He attended a private school, Clark's College in Ilford, where he says they taught him less than the more basic council school. As well as dyslexia he also has the motor skill disorder dyspraxia (developmental coordination disorder).
In one school year, he claims he only attended 33 times. He left school on his fifteenth birthday, to become a copy boy at the Fleet Street offices of the Yorkshire Post. He raced through a series of dead end jobs, before his call up for National Service in 1956, serving with the Royal Air Force in Singapore in 1957. The appropriation of his trumpet forced him to consider other creative outlets, and he bought a Rolleiflex camera.
He was demobbed in August 1958, and determined to pursue a career in photography, he bought a Canon rangefinder camera. Unable to obtain a place at the London College of Printing because of his school record, he became a second assistant to , in Charlotte Mews. He earned £3 10s (£3.50) a week, and acted as studio dogsbody. He was delighted to be called to an interview with photographer John French.
In 1959, Bailey became a photographic assistant at the John French studio, and in May 1960, he was a photographer for John Cole's Studio Five, before being contracted as a fashion photographer for British Vogue magazine later that year. He also undertook a large amount of freelance work.
Along with Terence Donovan and Brian Duffy, Bailey captured and helped create the 'Swinging London' of the 1960s: a culture of fashion and celebrity chic. The three photographers socialised with actors, musicians and royalty, and found themselves elevated to celebrity status. Together, they were the first real celebrity photographers, named by Norman Parkinson "the Black Trinity".
The film Blowup (1966), directed by Michelangelo Antonioni, depicts the life of a London fashion photographer who is played by David Hemmings, whose character was inspired by Bailey. The "Swinging London" scene was aptly reflected in his Box of Pin-Ups (1964): a box of poster-prints of 1960s celebrities including Terence Stamp, The Beatles, Mick Jagger, Jean Shrimpton, PJ Proby, Cecil Beaton, Rudolf Nureyev and East End gangsters, the Kray twins. The Box was an unusual and unique commercial release. It reflected the changing status of the photographer that one could sell a collection of prints in this way. Strong objection to the presence of the Krays by fellow photographer, Lord Snowdon, was the major reason no American edition of the "Box" was released, and that a second British edition was not issued. The record sale for a copy of 'Box of Pin-Ups' is reported as "north of £20,000".
At Vogue Bailey was shooting covers within months, and, at the height of his productivity, he shot 800 pages of Vogue editorial in one year. Penelope Tree, a former girlfriend, described him as "the king lion on the Savannah: incredibly attractive, with a dangerous vibe. He was the electricity, the brightest, most powerful, most talented, most energetic force at the magazine".
American Vogue's creative director Grace Coddington, then a model herself, said "It was the Sixties, it was a raving time, and Bailey was unbelievably good-looking. He was everything that you wanted him to be – like the Beatles but accessible – and when he went on the market everyone went in. We were all killing ourselves to be his model, although he hooked up with Jean Shrimpton pretty quickly".
Of model Jean Shrimpton, Bailey said:
She was magic and the camera loved her too. In a way she was the cheapest model in the world – you only needed to shoot half a roll of film and then you had it. She had the knack of having her hand in the right place, she knew where the light was, she was just a natural.
Since 1966, Bailey has also directed several television commercials and documentaries. From 1968 to 1971 he directed and produced TV documentaries titled Beaton, Warhol and Visconti. As well as fashion photography, Bailey photographed album sleeve art for musicians including The Rolling Stones and Marianne Faithfull. One of Bailey's most famous works depicts the Rolling Stones including Brian Jones, who drowned in 1969 while under the influence of drink and drugs. He is seen standing slightly apart from the rest of the group.
Bailey was hired in 1970 by Island Records' Chris Blackwell to shoot publicity photos of Cat Stevens for his upcoming album Tea for the Tillerman. Stevens, who is now known as Yusuf Islam maintains that he disliked having his photo on the cover of his albums, as had previously been the case, although he allowed Bailey's photographs to be placed on the inner sleeve of the album.
In 1972, rock singer Alice Cooper was photographed by Bailey for Vogue magazine, almost naked apart from a snake. Cooper used Bailey the following year to shoot for the group's chart topping 'Billion Dollar Babies' album. The shoot included a baby wearing shocking eye makeup and, supposedly, one billion dollars in cash requiring the shoot to be under armed guard. In 1976, Bailey published Ritz Newspaper together with David Litchfield. In 1985, Bailey was photographing stars at the Live Aid concert at Wembley Stadium. As he recalled later: "The atmosphere on the day was great. At one point I got a tap on my shoulder and spun round. Suddenly there was a big tongue down my throat! It was Freddie Mercury."
In 1992, Bailey directed the BBC drama Who Dealt? starring Juliet Stevenson, story by Ring Lardner. In 1995 he directed and wrote the South Bank Film The Lady is a Tramp featuring his wife Catherine Bailey. In 1998 he directed a documentary with Ginger Television Production, Models Close Up, commissioned by Channel 4 Television.
In October 2013, Bailey took part in Art Wars at the Saatchi Gallery curated by Ben Moore. The artist was issued with a stormtrooper helmet, which he transformed into a work of art. Proceeds went to the Missing Tom Fund set up by Ben Moore to find his brother Tom who has been missing for over ten years. The work was also shown on the Regents Park platform as part of Art Below Regents Park.
In September 2020, Bailey exhibited 50 previously unseen oil paintings at a London Fashion store. David Bailey Unseen adorns the walls of Flannels of Oxford Street. “I find painting relaxing,” says the photographer. 
In October 2020 Bailey's Memoir "Look Again" in co-operation with author James Fox was published by Macmillan Books a review on his life and work.
Bailey began working with fashion brand Jaeger in the late 1950s when Jean Muir landed the role of designer. After working alongside other fashion photographers such as the late Norman Parkinson, Bailey was officially commissioned by Vogue in 1962.
His first shoot in New York City was of young model Jean Shrimpton, who wore a range of Jaeger and Susan Small clothing, including a camel suit with a green blouse and a suede coat worn with kitten heels. The shoot was titled 'Young Idea Goes West'.
After 53 years Bailey returned to Jaeger to shoot their AW15 campaign. As menswear subject; James Penfold modelled tailored tweed blazers and a camel coat. Also on the shoot was model, philanthropist and film director Elisa Sednaoui along with GQ magazine's most stylish male 2003, Martin Gardner.
- 2001: Commander of the Order of the British Empire, as part of 2001 Queen's Birthday Honours.
- 2005: Centenary Medal and Honorary Fellowship (HonFRPS), Royal Photographic Society.
- 2016: Lifetime Achievement award, Infinity Awards, International Center of Photography, New York.
Painting and sculpture
Bailey paints and sculpts. Some of his sculptures were shown in London in 2010, and paintings and mixed media works were shown in October 2011.
In popular culture
In the 1970s Bailey lost some equipment in a robbery and replaced it with the new Olympus OM system equipment which was substantially smaller and lighter than contemporary competitors' equipment. He then appeared in advertising promoting the Olympus OM-1 35 mm single lens reflex camera. He subsequently appeared in a series of UK TV commercials for the Olympus Trip camera.
Bailey has been married four times: in 1960 to Rosemary Bramble; in 1965 to the actress Catherine Deneuve (divorced 1972); in 1975 to American fashion model and writer Marie Helvin; and in 1986 to the model Catherine Dyer (born 20 July 1961), to whom he remains married. He is a long-time vegetarian and refrains from drinking alcohol. An art-lover with a long-held passion for the works of Picasso, his Company address is in London and his wife is listed as a Director under her married name Catherine Caliope Bailey, together with their photographer son Fenton Fox Bailey. The family maintain a home on Dartmoor, near Plymouth. His youngest son b.June 1994 Sascha Taday Bailey, is an art curator.
- Box of Pin-Ups, 1964
- Goodbye Baby & Amen, 1969, 2017
- Warhol, 1974
- Beady Minces, 1974
- Papua New Guinea, 1975
- Mixed Moments, 1976
- Trouble and Strife, 1980
- Mrs. David Bailey, 1980
- Bailey NW1, 1982
- Black & White Memories, 1983
- Nudes 1981–1984, 1984
- Imagine, 1985
- If We Shadows, 2001
- The Lady is a Tramp, 1995
- Rock & Roll Heroes, 1997
- Archive One, 1999 (also titled The Birth of the Cool for USA)
- Chasing Rainbows, 2001
- Art of Violence, Kate Kray & David Bailey, 2003 (also titled Diamond Geezers)
- Bailey/Rankin Down Under, 2003
- Archive Two: Locations, 2003
- Bailey's Democracy, 2005
- Havana, 2006
- NY JS DB 62, 2007
- Pictures That Mark Can Do, 2007
- Is That So Kid, 2008
- David Bailey: 8 Minutes: Hirst & Bailey, 2009 With Damien Hirst
- EYE, 2009
- Flowers, Skulls, Contacts, 2010
- British Heroes in Afghanistan, 2010
- The David Bailey SUMO, 2019
- "Look Again", 2020
- National Portrait Gallery 1971
- One Man Retrospective Victoria & Albert Museum 1983
- International Center of Photography (ICP) NY 1984
- Curator "Shots of Style" Victoria & Albert Museum 1985
- Pictures of Sudan for Band Aid at The Institute for Contemporary Arts (ICA) *1985
- Auction at Sotheby's for Live Aid Concert for Band Aid 1985
- Bailey Now! Royal Photographic Society in Bath 1989
- Numerous Exhibitions at Hamiltons Gallery, London. 1989 to now
- Fahey Klein Gallery, Los Angeles 1990
- Camerawork Photogallerie, Berlin. 1997
- Carla Sozanni. Milan. 1997
- A Gallery for Fine Photography, New Orleans. 1998
- Touring exhibition "Birth of the Cool" 1957–1969 & contemporary work
- Barbican Art Gallery, London – 1999
- National Museum of Film, Photography & Television, Bradford. 1999–2000
- Moderna Museet, Stockholm, Sweden. 2000
- City Art Museum, Helsinki, Finland 2000
- Modern Art Museum, The Dean Gallery, National Galleries of Scotland, Edinburgh 2001
- Proud Gallery London Bailey /Rankin Down Under
- Gagosian Gallery. Joint with Damien Hirst "14 Stations of the Cross" 2004
- Gagosian Gallery. Artists by David Bailey. 2004
- Democracy. Faggionato Fine Arts 2005
- Havana. Faggionato Fine Arts 2006
- Pop Art Gagosian London 2007
- Galeria Hilario Galguera Mexico 2007
- National Portrait Gallery – Beatles to Bowie 2009
- Bonhams, London. Pure Sixties Pure Bailey 2010
- Pangolin London. Sculpture + 2010
- The Stockdale Effect, Paul Stolper Gallery, London 2010
- David Bailey's East End. Compressor House, London, 2012.
- David Bailey's East End Faces London February/May 2013
- Bailey's Stardust, National Portrait Gallery, London 2014
- Bailey's Stardust, National Gallery, Edinburgh 2015
- David Bailey Stardust, PAC – Padiglione di Arte Contemporanea, Milano (Italy) 2015
- Heaf, Jonathan (20 January 2012). "David Bailey photography interview – GQ.COM (UK)". GQ. Retrieved 10 April 2012.
- "BBC Four – David Bailey: Four Beats to the Bar and No Cheating". bbc.co.uk. 2012. Retrieved 10 April 2012.
- The Houghton Mifflin Dictionary of Biography. Houghton Mifflin Harcourt. 15 July 2003. p. 96. ISBN 9780618252107. Retrieved 10 April 2012.
- "Passed/Failed: An education in the life of David Bailey, photographer Archived 26 September 2006 at the Wayback Machine", The Independent.
- "David Bailey was a scowling, socially mobile rude boy". The Independent. 2 January 2016. Retrieved 15 April 2020.
- Levy, Shawn (2002). Ready, Steady, Go!: The Smashing Rise and Giddy Fall of Swinging London. New York: Doubleday. pp. 16–18. ISBN 0-385-49857-8.
- "David Bailey: Godfather of Cool", BBC.
- Pittman, Joanna (20 August 2009). "David Bailey:still snapping away at 71". The Times. London. Retrieved 20 August 2009.
- PDN Legends Online: David Bailey. Retrieved 15 November 2013.
- Petkanas, Christopher (24 January 2011). "Photographer Who Broke Molds". The New York Times. Retrieved 24 January 2011.
- Ellison, Jo (July 2010). "Rogue's Gallery". British Vogue.
- Islam, Yusuf; Alun Davies (1970). "A conversation with Yusuf Islam & Alun Davies". Interview (upon the anniversary of Island Records) of Stevens and Davies. UK. Retrieved 26 July 2015 – via YouTube.
- Wilkinson, Carl (17 October 2004). "Live aid in their own words". The Observer. London. Retrieved 3 April 2013.
- "Biography: David Bailey". CNN. 3 November 2006. Retrieved 1 September 2018.
- Ash, Laurien (2 October 2013). "Damien Hirst and David Bailey don their Stormtrooper helmets for 'Art Wars'". The Daily Telegraph. London. Retrieved 12 January 2017.
- "Info". Art Below. Retrieved 12 January 2017.
- Editors, Luxe Review (6 September 2020). "David Bailey Unseen exhibition unites art and fashion in a surprising way". The Luxe Review.CS1 maint: extra text: authors list (link)
- Sturges, Fiona (29 October 2020). "Look Again by David Bailey review – no reflection, no regret". The Guardian. ISSN 0261-3077. Retrieved 1 November 2020.
- "David Bailey". Vogue UK. Retrieved 9 December 2015.
- "The Campaign: AW15". Jaeger. Jaeger. Archived from the original on 7 October 2015.
- "No. 56237". The London Gazette (Supplement). 16 June 2001. pp. 7–8.
- Royal Photographic Society's Centenary Award
- "Infinity Awards". International Center of Photography. 3 February 2016. Retrieved 3 February 2016.
- Durón, Maximilíano (3 February 2016). "ICP Gives 2016 Infinity Awards to Walid Raad, Zanele Muholi, David Bailey, More". ARTnews. Retrieved 3 February 2016.
- Stuart, Jeffries (26 August 2010). "Out of his skulls". The Guardian.
- "1970s Olympus Trip 35 Commercials Starring British Photographer David Bailey".
- "UK Company Search". Retrieved 20 October 2015.
- "Fenton Fox BAILEY - Personal Appointments (free information from Companies House)". find-and-update.company-information.service.gov.uk. Retrieved 1 November 2020.
- "UK Electoral Roll". Retrieved 20 October 2015.
- Exhibition notice Archived 31 July 2012 at the Wayback Machine, Create London. Retrieved 28 July 2012.
- "East End Faces, William Morris Gallery". The Daily Telegraph. London. 21 February 2013.
- Brown, Mark (5 September 2013). "Unseen pictures to feature in David Bailey show at National Portrait Gallery". The Guardian. Retrieved 30 January 2014.
- David Bailey on IMDb
- David Bailey at FMD
- Liz Walker interviews David Bailey, September 1990
- Text of 1994 interview.
- 2000 interview (text and video)
- 2006 CNN interview (text and video)
- David Bailey British Vogue Covers Archive
- Francis Hodgson, "David Bailey: Still troubling after all these years"