Bokenam wrote a series of thirteen legends of holy maidens and women. These are written chiefly in seven and eight-lined stanzas, and nine of them are preceded by prologues. Bokenam was a follower of Chaucer and Lydgate, and doubtless had in mind Chaucer's Legend of Good Women. His chief, but by no means his only, source was the Legenda Aurea of Jacobus de Voragine, archbishop of Genoa, whom he cites as Januence. The first of the legends, Vita S[an]c[t]ae Margaretae, virginis et martyris, was written for his friend, Thomas Burgh, a Cambridge monk. Others are dedicated to pious ladies who desired the history of their name-saints.
The Arundel MS. 327 (in the British Museum) is a unique copy of Bokenam's work; it was finished, according to the concluding note, in 1447, and presented by the scribe, Thomas Burgh, to an unnamed convent that the nuns may remember him and his sister, Dame Betrice Burgh.
The poems were edited (1835) for the Roxburghe Club with the title Lyvys of Seyntys …, and by Dr. Carl Horstmann as Osbern Bokenams Legenden (Heilbronn, 1883), in Eugen Kölbing's Altengl. Bibliothek, vol. i. Both editions include a dialogue written in Latin and English taken from William Dugdale's Monasticon Anglicanum (ed. 1846, vol. vi, p. 1600); this is a dialogue between a "Secular asking and a Frere answerynge at the grave of Dame Johan of Acres shewith the lyneal descent of the lordis of the honore of Clare fro ... MCCXLVIII to ... MCCCLVI". Bokenam wrote, as he tells us, plainly, in the Suffolk speech. He explains his lack of decoration on the plea that the finest flowers had been already plucked by Chaucer, Gower and Lydgate.