The album was made with an early line-up of Adam and the Ants, which disbanded after the album was released. Guitarist Matthew Ashman and drummer David Barbarossa went on to form Bow Wow Wow with then-Ants bassist Leigh Gorman (who had only played one gig with the Ants and was not involved in any studio recordings). Original bassist Andy Warren had departed shortly after recording the album to join former Ants guitarist Lester Square in The Monochrome Set. Many of the songs, notably "Cleopatra" and "Never Trust a Man (With Egg on his Face)", remained a part of Adam Ant's live repertoire throughout his career, both with the Ants and later as a solo artist.
The "Dirk" of the title refers to classic British film icon Dirk Bogarde.
Dirk Wears White Sox was released on 30 October 1979.
The album was re-released in 1983, featuring a different album cover taken from a December 1979 video for the song "Zerox". "Catholic Day" and "Day I Met God" were dropped and "Cartrouble" appears in its single version. This edition also adds three songs from the same era not on the original LP: "Kick!", "Zerox", and "Whip in My Valise". It was re-issued again in 1995 by Sony, featuring the original black-and-white album art in somewhat cropped form. The lettering on the sleeve was recreated in the style of the original and does not feature the stroke through the letter O in the word "Sox"; it also substitutes a letter "Z" in place of the zig-zagged "S" in the word "Ants" (previously a common practice among unofficial merchandisers around the time of the album's original release).
In his retrospective review, Chris Woodstra of AllMusic wrote "while the somewhat pretentious, overly arty lyrics and inexperienced playing are a drawback, the album offers a fascinating look at the Ants' formative years, capturing a raw energy that would be sacrificed for more polish on subsequent releases."