Start with The Cruel Prince, and read the trilogy in order: The Cruel Prince, then The Wicked King, then The Queen of Nothing. This is one of the rare series where order genuinely is not a question — each book ends on a reversal that the next one opens by paying off, and the last thirty pages of The Cruel Prince are the hinge the whole thing turns on. Go in unspoiled.
What actually confuses readers is the material around the trilogy. There are two novellas, one of which ruins the second book if read early and one of which is a coda that ruins the third. There is a later duology set in the same court. And there is an entirely separate Holly Black faerie sequence from the early 2000s that shares the world's logic but none of its characters, which is why search results mix them together.
The trilogy
The Cruel Prince (370 pages in our record) puts a human girl raised in the High Court of Faerie by the man who murdered her parents into the business of making herself indispensable to people who despise her. The Wicked King is the shortest and fastest of the three at 332 pages, and ends on the series' most-argued-about betrayal. The Queen of Nothing resolves the exile and the crown in 336 pages. Read the second and third close together; the third assumes the sting of the second is still fresh.
Content, stated plainly: these are young-adult novels containing poisoning, torture, on-page killing, and a central relationship built substantially out of coercion and mutual manipulation. That is the point of them rather than an accident, but it is worth knowing before handing them to a younger reader.
The two novellas, placed correctly
The Lost Sisters is Taryn's account of the first book, written as a letter to Jude and running to 26 pages in our record. It goes between The Cruel Prince and The Wicked King. Read earlier and it simply hands over a betrayal you have not experienced yet.
How the King of Elfhame Learned to Hate Stories is an illustrated collection of vignettes from Cardan's childhood, at 200 pages with Rovina Cai's artwork. Its final section is set after the trilogy ends, which is the reason it must come after The Queen of Nothing. It is a coda, not a companion.
The sequel duology
The Stolen Heir and The Prisoner's Throne are set eight years after the trilogy, following Suren — the child queen of the Court of Teeth from the earlier books — and Oak. They read as a genuine continuation rather than a spin-off, and they depend on knowing how the trilogy ended. The two are effectively one book split down the middle, and the first ends on a cliffhanger the second resolves, so do not start The Stolen Heir unless you intend to read both.
The older faerie books
The Modern Faerie Tales are the harsher, grubbier, contemporary version of the same material. Tithe is Black's 2002 debut: a sixteen-year-old drifting around the New Jersey shore discovers she is a changeling being lined up as a sacrifice. Valiant is near-standalone, about a runaway living in the New York subway and serving a troll, and is the strongest of the three on its own terms. Ironside returns to Kaye and closes the quest set up at the end of Tithe. They are often sold as one omnibus but resolve individually.
The Darkest Part of the Forest is the bridge between the two sequences — a town that has learned to live beside the Folk, a boy in a glass coffin, and the courtly cruelty that would become Elfhame. It is the closest in tone to The Cruel Prince, so read it last of this group.
Outside Faerie
The Coldest Girl in Coldtown is vampires quarantined in walled cities that livestream their own parties, and the best standalone Black has written. Doll bones is a Newbery Honor middle-grade novel about three friends, a bone-china doll and the exact age at which pretending stops being allowed — much younger than everything else here and the most quietly serious book on the list. Book of Night is her first novel for adults, a con-artist story in a world where shadows can be altered and sold.
The full ordering, novellas included, is laid out at the Folk of the Air reading path.