Start with The Importance of Being Earnest. It takes an hour, it is the funniest thing he wrote, and it is the purest sample of the sensibility — nothing in it is trying to be about anything, which is exactly the point he spent his critical prose defending.
The obvious alternative is The Picture of Dorian Gray, and it is the wrong first move for a practical reason: the novel is doing something Wilde does nowhere else, and read cold it gets mistaken for a moral fable, which is close to the opposite of its intent. Come to it second, once the comedies have taught you how he uses a sentence.
The novel, and which edition to buy
The Picture of Dorian Gray exists in two substantially different texts. The shorter magazine version appeared first; the longer book version added six chapters and softened several passages after the first had been attacked. Modern editions print one or the other, sometimes without making it obvious. The longer text is the standard one and the one most editions mean by the title; the shorter is more direct. Check the introduction before you buy — this is the single most common Wilde purchasing mistake.
The short fiction
The Happy Prince and other tales collects the fairy stories, and they are not children's stories in any comfortable sense — most of them end in death or ruin, delivered in the plainest prose he ever wrote. The Canterville Ghost is the comic counterweight, a haunted-house story in which the Americans terrorise the ghost.
The society plays, in order of writing
Lady Windermere's Fan is the first and the most conventional in its machinery. A Woman of No Importance is the weakest of the four and the most openly angry about the double standard it dramatises. An Ideal Husband is the best of the three that precede The Importance of Being Earnest, and it is the one with an actual moral argument underneath the epigrams.
Salome stands apart. Wilde wrote it in French, and the Lord Chamberlain refused it a licence for the English stage, so it circulated as a text long before it was performed. It reads nothing like the comedies: incantatory, repetitive, deliberately airless.
The criticism
Intentions holds the critical dialogues, including the argument that life imitates art rather than the reverse — this is where Wilde is doing philosophy rather than performing it. The Soul of Man Under Socialism is the political essay, and it surprises most readers: it is far less interested in economics than in the claim that art requires individuals who are not obliged to be useful.
Prison, and where to stop
De profundis is the letter written to Lord Alfred Douglas from Reading Gaol. The edition history here is genuinely tangled — for decades the only available texts were heavily cut, and the complete letter was not published in full until 1962. An abridged De Profundis is a different and much smaller book than the complete one, so check what you are getting.
The Ballad of Reading Gaol is the last thing he published and the natural place to end. It is written in a flat ballad measure with none of the wit, and coming to it after the comedies is the whole point of reading Wilde in order.
Wilde was imprisoned for gross indecency, and the final two works cannot be read apart from that. The full ordered sequence, with the plays in composition order, is on the path below; you can also browse more Wilde context on his subject page.
Follow the full ordered path here: Oscar Wilde: What to Read First, and in What Order.
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