The best books aren't static stories, but living entities with meanings that change and grow along with you. That's why I strongly recommend reading thses classics.
"The Sun Also Rises," by Ernest Hemingway
Not only can you get your literary passport stamped twice with Hemingway's romp through Paris and Pamplona, but you can enjoy an immersive mood piece about the highs and lows of drunken, rambling youth.
"The Secret History," by Donna Tartt
Tartt's contemporary Greek tragedy about an unraveling clan of Classics majors is enchanting but may seem a little overwrought once your college days are decades behind you.
"A Collection of Essays," by George Orwell
You ripped through "Animal Farm" and "1984" in high school. Now it's time to take some of Orwell's insight straight, sans pig metaphors. He discusses British Imperialism, but it's not all political: "Such, Such Were the Joys," an essay about prep school, is particularly delightful.
"Hamlet," by William Shakespeare
We strongly advise against entering your 30s without having read (and we mean really read and fully ingested) one of Shakespeare's tragedies. If you have to pick just one, pick "Hamlet." Perhaps it'll help you with that pesky indecision you're likely experiencing if you're a 20-something.
"Hateship Friendship Courtship Loveship Marriage," by Alice Munro
Munro writes short stories about small worlds, often centered around Canadian women like herself. She reminds us that quiet foibles and triumphs can be as beautiful and significant as sweeping, epic tales -- an important insight to keep in mind as you leave your more self-centered, dramatized youth behind.
"Native Son," by Richard Wright
Wright's book is literary naturalism at its finest, creating empathy for the impoverished and downtrodden -- an important lesson to learn if you haven't already.
“Portrait of a Lady,” by Henry James
Protagonist Isabel Archer's transition from a wide-eyed and fiercely independent girl to a resigned woman stuck in a miserable marriage can serve as more than a warning sign. Her charming insights, along with the optimism of her cousin Ralph, make for an incredible read.
“The Golden Notebook,” by Doris Lessing
Protagonist Anna attempts to tie her four journals, each focusing on a different theme of her life (The Cold War, women's liberation in England, etc.), together into one, cohesive story. You may find yourself doing this in your 30s as well.
“A Room of One's Own,” by Virginia Woolf
Woolf argues that your own personal space is necessary for the peace of mind needed to create good art. Whether or not you agree with her, this long essay explores not just the importance of financial freedom, but women's emotional freedom, too.
"The Unbearable Lightness of Being," by Milan Kundera
Kundera offers keen insight into gender dynamics and the universal struggle to achieve both independence and meaningful relationships -- sounds familiar, right, 20-somethings?