Digby Fairweather has been a full-time jazz musician since 1 January 1977, and had worked part-time for seven years before this with several local jazz bands in Essex and London. He recorded his first album in 1975 with Alex Welsh's band (as deputy for Welsh). When turning professional, Fairweather helped found the Keith Nichols Midnite Follies Orchestra. From 1978 he recorded solo albums, and joined a quartet known as Velvet, with guitarists Denny Wright and Ike Isaacs plus bassist Len Skeat. Before becoming a professional musician he was a librarian and has retained a strong interest in jazz bibliography and archiving.
In 1979, Fairweather became co-director of the nonprofit Jazz College along with pianist Stan Barker. He also joined the Pizza Express All Stars. From 1983 he began leading bands of his own and helped to revitalise the Kettners Five, co-led with veteran double-bassist Tiny Winters. In 1983, Fairweather and Winters collaborated in a touring tribute to Nat Gonella, and also worked on various projects together over the next decade. Fairweather's musical style has been influenced by a number of artists, particularly Louis Armstrong, Ruby Braff, Billy Butterfield, Bobby Hackett, Red Nichols and Gonella. Digby’s Half Dozen was formed in 1995 and toured and recorded with singer George Melly in the later years of his career (2003–07). Thereafter Fairweather's band has toured with former Manfred Mann lead singer Paul Jones in their presentation titled 'Rocking in Rhythm' (2007–present). Apart from his playing and bandleading, Fairweather has long pursued a parallel career as a broadcaster and writer on jazz.
From 1985 to 1988 he worked and recorded with Brian Priestley's Special Septet and Tony Milliner's Mingus Music and authored the book How to Play Trumpet. By 1990 he had embarked on a dual vocation as broadcaster for BFBS, BBC World Service, Jazz FM (1991–92) and BBC Radios 2/3 (including occasional deputising for Humphrey Lyttelton on the show Best of Jazz and successively presented Jazz Parade and Jazz Notes for BBC Radio 2/3 (1992–98). In 1987 Fairweather founded the Association of British Jazz Musicians and the National Jazz Archive. That same year he formed the Jazz Superkings (with Dave Shepherd, Brian Lemon, Allan Ganley, et al). Fairweather also helped bring jazz musicians into the British Musicians' Union by proposing, then founding, its Jazz Section in 1992. In 1994 (with trombonist Pete Strange) he co-founded The Great British Jazz Band and continues to teach and do solo work. Following the death of Humphrey Lyttelton, he was invited to succeed Lyttelton as the Patron of the Birmingham International Jazz Festival. In 2013 he continues to lead his Half Dozen (winners of the Best Small Group category at the 2012 British Jazz Awards) and to perform as a soloist.
- BBC Jazz Society Musician of the Year (1979)
Freedom, City of London (1992) British Jazz Award (trumpet)/1992 British Jazz Award 1992/Services to Jazz/dittoBenno Haussman Award (1993, Cork Jazz Festival) Freedom of Southend on Sea (Millennium Role of Honour/2000) British Jazz Award:'Top Small Group' (Digby's Half Dozen);2005/6/8/9/10/11/12
- Havin' fun (Black Lion, 1979)
- Going out stepping (Black Lion, 1979)
- Songs for Sandy (Hep Records, 1981)
- Anytime, any place, anywhere (Hep Records, 1982)
- A Portrait of Digby Fairweather (Black Lion, 1991)
- Mick Potts Tribute Concert (Flat Five Records, 1993)
- Squeezin' the Blues Away (with Tony Compton/FMR Records,1994)
- The Quality of Mercer (with Susannah McCorkle/Keith Inggham/Jazz Alliance, 1996)
- Twelve Feet off the Ground (with Digby Fairweather Half Dozen/Flat Five Record, 1998)
- Singing and Swinging the Blues (with Half Dozen/George Melly/Robinwood Productions, 2003)
- Things ain't what they used to be (with Half Dozen/Robinwood Productions, 2003)
- The Ultimate Melly (Candid Records,2006)
- Two Part Conversations (With Craig Milverton/Raymersound,2006)
- Partners in Time (With Pete Strange/Rose Cottage Records (RCR001), 2006)
- Farewell Blues (with Half Dozen/George Melly/Lake Records, 2007)
- Jazz at the Stone Hall (with Dave Claridge New Orleans Band)/Rose Cottage Records (RCR 002), 2009)
- Crackerbarrel Music (Hainault Records) 2011
- To Frederick with Affection (Rose Cottage Records (RCR 004),2012)
- Fairweather, Digby (2002). Notes from a Jazz Life. London: Northway Books. ISBN 978 0953704019. (autobiography)
- Fairweather, Digby (2005). Nat Gonella: A Life in Jazz. London: Northway Books. ISBN 978 0953704071.
- Priestley, Brian; Ian Carr, Digby Fairweather (2007). The Rough Guide to Jazz. Rough Guides. ISBN 1843532565.