Lady Lilith was commissioned by Frederick Leyland in early 1866 and delivered to him in early 1869 at a price of £472. Two studies, dated to 1866, exist for the work, but two notebook sketches may be from an earlier date. The painting focuses on Lilith, but is meant to be a "Modern Lilith" rather than the mythological figure. She contemplates her own beauty in her hand-mirror. The painting is one of a series of Rossetti paintings of such "mirror pictures." Other painters soon followed with their own mirror pictures with narcissistic female figures, but Lady Lilith has been considered "the epitome" of the type.
On 9 April 1866 Rossetti wrote to Frederick Leyland descrbing his progress on Lady Lilith:
"As you continue to express a wish to have a good picture of mine, I write you word of another I have now begun, which will be one of my best. The picture represents a lady combing her hair. It is the same size as Palmifera – 36 x 31 inches, and will be full of material, – a landscape seen in the background. Its color chiefly white and silver, with a great mass of golden hair."
Lady Lilith's frame was adorned with one of Rossetti's sonnets:
Of Adam's first wife, Lilith, it is told
(The witch he loved before the gift of Eve,)
That, ere the snake's, her sweet tongue could deceive,
And her enchanted hair was the first gold.
And still she sits, young while the earth is old,
And, subtly of herself contemplative,
Draws men to watch the bright web she can weave,
Till heart and body and life are in its hold.
The rose and poppy are her flowers; for where
Is he not found, O Lilith, whom shed scent10
And soft-shed kisses and soft sleep shall snare?
Lo! as that youth's eyes burned at thine, so went
Thy spell through him, and left his straight neck bent
And round his heart one strangling golden hair.