This is a poem entirely built on the unexpected, with traditional poetic images, such as that of the "evening... spread out against the sky" juxtaposed alongside the jarring picture of "a patient etherized upon a table." The poem's images are sometimes surreal, but, more usually, simply show common images in unusual ways, as where the personified fog "licked its tongue into the corners of the evening," "rubbing its back" around the buildings, until the reader cannot help but to picture it as a cat of sorts. These feline qualities are not typical of the attributes normally allotted by poets to fog and smoke. T.S. Eliot takes advantage of the knowledge of what is expected and maintains interest by subverting these expectations.

The picture of the speaker "pinned and wriggling on the wall" is followed up the unexpected "butt-ends of my days and ways." Later, the straightforward image of "lonely men in shirtsleeves leaning out of windows" runs directly into Prufrock's inexplicable musing: "I should have been a pair of ragged claws, scuttling across the floors of silent seas." In both cases, the first image is traditional; the second, startling. Sometimes we see this pattern happen the other way about, as where Prufrock describes, "squeezing the universe into a ball"; this unexpected picture then transmutes itself into a familiar Biblical motif as it "rolls" into the reference to Lazarus, at which point we recognize the allusion to the stone rolled away from the tomb. Likewise, the Shakespearean references soothe the reader with their familiarity, before the unexpected ("I shall wear the bottoms of my trousers rolled") appears once more.

T. S. Eliot's poem "The Love Song of J. Alfred Prufrock" contains many striking contrasts and juxtapositions of imagery, starting with the title itself. The form of address, "J. Alfred Prufrock," is what one might expect to see on a formal business card, and it is strikingly incongruous to see it paired with "love song." In fact, the persona of Prufrock, a hesitant, polite, middle-aged man, is in striking contrast with the usual young romantic characters populating love songs. The setting also contrasts with our expectations of the love song genre, being gritty urban London as opposed to the idyllic countryside of the pastoral.

One of the first startling juxtapositions in the poem has do do with the nature of love, contrasting the seedy London slums and sordid sexual encounters, possibly with prostitutes ("The muttering retreats/Of restless nights in one-night cheap hotels") with fashionable drawing rooms where:

In the room the women come and go
Talking of Michelangelo.

The Prufrock character's clothing shows him to be clearly of this upper-middle class world ("My morning coat, my collar mounting firmly to the chin,/My necktie rich and modest, but asserted by a simple pin ...") and yet, in his search for love, he is not fundamentally different than any other single man, something he acknowledges, comparing himself with other London men:

..., I have gone at dusk through narrow streets
And watched the smoke that rises from the pipes
Of lonely men in shirt-sleeves, leaning out of windows? ...

The final striking contrast of imagery in the poem is one where Eliot sets a vision of Prufrock, descending into a cautious and proper old age against a romantic version of unobtainable mermaids. Prufrock reflects:

I grow old ... I grow old ...
I shall wear the bottoms of my trousers rolled.
Shall I part my hair behind? Do I dare to eat a peach?
I shall wear white flannel trousers, and walk upon the beach.

This beach evokes the image of mermaids, and what is the closest part of the poem to a conventional love song, in an almost Tennysonian style:

I have seen them riding seaward on the waves
Combing the white hair of the waves blown back
When the wind blows the water white and black.

However, as Prufrock has pointed out, his world is one contrasting with that of romantic love rather than participating in it, and he wryly comments at the start of the song: "I do not think that they will sing to me."