- Attention Whore: Arguably. At the very least he impersonates one in Mike and Psmith when he claims that his false confession to save Mike was due to "[t]he craze of notoriety."
- Batman Gambit: Psmith's occasional modus operandi. In Psmith in the City, he stays in his job by cultivating a rapport with his supervisor, despite his occasional flagrant disregard of the rules.
- Big Brother Instinct
- Book Dumb: Gets expelled from Eton and sent to Sedleigh instead. Nonetheless an insightful and brilliant social manipulator.
- Breakout Character: Introduced as a supporting character to Mike Jackson, but took over the series to the extent that Mike is now invariably remembered as Psmith's supporting character.
- Carry a Big Stick: In Psmith, Journalist, Psmith uses Billy Windsor's walking stick (purchased specifically for such a situation) to fend off a group of New York City thugs. When one of the thugs shouts, "He's got a big stick!" Psmith mutters to himself, "I and Roosevelt."
- The Champion: For Mike.
- Character Filibuster: His standard method of speaking.
- Cloudcuckoolander: Psmith pretends to be one because it amuses him and throws people off their guard; nevertheless, he is always aware of and in control of the situation.
- The Cuckoolander Was Right: Sure, he acts like a complete lunatic, but he's also utterly brilliant and nigh-invincible.
- Comical Overreacting / The Comically Serious: Swings wildly between the latter and the former. (Death threats and angry mobs are nothing serious. Having to take public transport is a tragedy.)
- Didn't Think This Through: A side effect of living by the Indy Ploy.
- Dissonant Serenity: Whenever there's any kind of a skirmish.
- Embarrassing First Name: "In conversation you may address me as 'Rupert' (though I hope you won't)."
- Fleeting Passionate Hobbies: Becomes briefly obsessed with things like running a newspaper.
- Gentleman Thief: Merely practical socialism.
- Genre Savvy: Upon meeting Mike, Psmith lists several Stock Characters in Boarding School stories, asking Mike which one he is.
- Happily Married: According to Word of God, he and Eve, eventually (when the series ends, they're engaged).
- Hat Damage: Psmith's hat takes a bullet during a shoot-out in Psmith, Journalist. He doesn't take it too well.
- Heterosexual Life-Partners: With Mike. Just to cement it, they end up marrying (respectively) Phyllis and Eve, themselves possible examples of this trope.
- Hidden Heart of Gold: When Mike tries to thank him for sacrificing himself to save Mike from expulsion, he acts upset and pretends to have no idea what Mike is talking about.
- High School Hustler: Psmith's original role. Even after he leaves school, his interactions with authority figures retain some of the same style.
- Hypocritical Humor: Psmith often refers to himself as "a man of few words".
- Insane Troll Logic: One of his many rhetorical skills ("How do you propose to strengthen the Navy by burning boats?")
- Love at First Sight: with Eve in Leave It to Psmith.
- Mad Libs Catch Phrase: "The cry goes round..." and variants thereof. Also, "Work, the ___ of the ___ and the ___ of the ____," which he eventually fills in with "Work, the what's-its-name of the thingummy and the thing-um-a-bob of the what d'you-call-it."
- My Favorite Shirt: His reaction to having his hat destroyed in Psmith, Journalist. He becomes determined to make the culprits pay...for the hat, and, in fact, succeeds.
- Neat Freak: Often described as flicking minute specks of dust or lint from his clothing.
- Standing Between the Enemies: Mike and Psmith contains an amusing subversion. Just as Mike and Adair are on the verge of beating each other senseless, Psmith stands between them and tells them not to fight...because they're in his room and they should be fighting outside. He proceeds to lead them outdoors and referree the battle.
- Sudden Name Change: Originally named "Rupert", Psmith gets his first name changed to "Ronald" to enforce the One Steve Limit in Leave It to Psmith.
- We Help the Helpless: His newspaper advertisement in Leave it to Psmith states that he's willing to do anything for money, from walking dogs to commiting crimes, "provided it has nothing to do with fish".
- Workaholic: Parodies this trope aggressively in Psmith in the City. He actually hates the job and spends most of his time cheerfully slacking off.
- Achilles in His Tent: The Trope Namer incident from The Iliad is referenced to explain why Mike refuses to play cricket at Sedleigh.
- Book Dumb: Brilliant cricketer, not so good in school.
- Chronic Hero Syndrome: In Psmith in the City Psmith accuses Mike of developing an addiction to sacrificing himself for others, likening it to "dram-drinking".
- Class Clown: Was often in trouble for "ragging" back at Wrykyn.
- The Confidant: One of Mike's duties as Psmith's secretary.
- Demoted to Extra: In Psmith in the City he and Psmith are still on roughly equal footing in terms of page time, but by Psmith, Journalist he's become a side character.
- Didn't Think This Through: Tends to make the quickest, most practical move required to save someone without fully realizing the consequences until it's too late.
- Dumb Jock: Not dumb per se, but it's obvious he'd be doing better in school if it were not for his single-minded pursuit of athletic interests (namely, cricket). This is part of the reason his father sends him to Sedleigh, a school with less emphasis on athletics.
- Heterosexual Life-Partners: With Psmith.
- Innocent Blue Eyes: Subverted: "As the blue-eyed hero he would have been a rank failure."
- Last Name Basis: "Mike" in the narration, but "Jackson" (or "Comrade Jackson" to Psmith) in the dialogue. Boys at British boarding schools went by their surnames.
- Mirror-Cracking Ugly: Psmith accuses him of being this in Psmith in the City.
- Name's the Same: Michael Jackson?
- The Pirates Who Don't Do Anything: He's Psmith's personal secretary and adviser, supposedly. (It's mostly just Psmith's excuse for keeping him around.)
- Put on a Bus: In the last two books.
- The Quiet One: Certainly seems this way by association with Psmith.
- Unfazed Everyman: Doesn't appear to find Psmith (all that) strange.
- Big Man on Campus: Mostly due to sheer fervor and force of personality.
- Suspiciously Similar Substitute: For Mike.
- Heterosexual Life-Partners: with Phyllis, Mike's wife.