The next series after the original gossip girl. This series follows Jenny at Waverly Prep.
- Jennifer Tallulah "Jenny" Humphrey, the main character of The It Girl, arrives at Waverly Academy after having been expelled from Manhattan's Constance Billard School for Girls. Jenny is eager to reinvent herself as 'New Jenny,' a more confident and more popular version of her former self, and to make an impression on her new classmates. Although Jenny gets off to a rocky start at Waverly, the attention she receives from the other students generally gets more positive as the series progresses.
- Callie Vernon, with her strawberry-blond hair and warm hazel eyes, her all-preppy look suits her position as daughter of the governor of Georgia. Prior to the beginning of the series, Callie was best friends with Brett Messerschmidt and Tinsley Carmichael, and the three of them were the most popular girls at Waverly. However, the three of them got caught taking ecstasy during their sophomore year, which resulted in the expulsion of Tinsley and the probation of Brett and Callie. Callie tends to turn to Tinsley for friendship and support more than anyone else, partly due to her deep-seated envy and admiration of her friend who always seems to have it together. The two usually team up against Jenny, whom Callie resents for stealing the beloved Easy Walsh away from her. However, Callie and Jenny do get along but their relationship is usually complicated by their ever changing love triangle with Easy Walsh.
- Brett Lenore Messerschmidt; smart, driven, and an all-rounder aiming to get into Brown, Brett is also one of Waverly's elite. She stands out from her aristocratic classmates due to her jaded appearance: her hair is dyed red and she habitually wears seven gold earrings in one of her ears. She loves Dorothy Parker and often quotes the author to herself. Brett claims to have lost her virginity, and that her parents are doctors who run an organic farm in East Hampton but in actuality, she is a virgin, and her parents are nouveau riche from New Jersey (her father being a plastic surgeon). Brett is the junior class prefect and a member of the Disciplinary Committee.
- Tinsley Adea Carmichael, the leader of Waverly's elite, makes a dramatic return in Notorious, after being unceremoniously kicked out at the end of her sophomore year for getting caught taking ecstasy with Callie Vernon and Brett Messerschmidt. It is revealed that Tinsley was the only one who was expelled because she was the only one who confessed to taking the drugs; Brett and Callie both denied it. She was accepted back into Waverly when the school authorities learned that she spent her summer in Africa producing a documentary with her father.
- Easy Walsh is an artsy, good-looking young man with a passion for both art and horseback riding. He is involved with a multiple girls throughout the series including Tinsley, Callie and Jenny. Although a part of the gossiping and drama filled society within his private school,he is very moralistic. He always wants and desires for the "right thing" to be done, however he is hypocritical in this sense in that he often commits questionable actions (e.g. "Stealing" Callie away from her boyfriend, pursuing a relationship with Jenny while dating Callie). Although he commits said questionable actions he has a very present conscious and feels remorse for his actions. Example: "[Easy] had always been ashamed of the shady way [Callie and him] had gotten together behind Brandon's back..." (Notorious page 62)
- Heath Ferro is similar to the character of Chuck Bass in Gossip Girl. An attractive, wealthy, egotistical womanizer, Heath is just as good at acting obnoxious and being a gossip as any girl at Waverly. Yet, he has a dorky side which includes being a fan of comic books and superheroes.He and his roommate Brandon Buchanan do not always get along due to Heath's messy habits. In the first It Girl novel, he was nicknamed "Pony" because he got more ass than a pony at a county fair. Despite the suggestions otherwise, in Unforgettable, Heath proves himself to be trustworthy when he keeps a lesbian relationship a secret. However, he falls in love with Kara, who initially rejected him due to his teasing of her during freshman year. For someone who never really cared about his relationships, Heath was surprisingly deeply hurt about the breakup. In Adored, he was mentioned to have been looking out for Kara during the Inferno party he hosted, probably in hopes of getting back with her. Heath and Brandon's relationship throughout the series improved somewhat, mostly in part to his break-up with Kara which allowed Brandon and Heath to empathize with each other.
- Brandon Buchanan is a ass whole. Despite being dumped by Callie Vernon for Easy Walsh, he remains hopelessly in love with Callie, hoping to win her back someday. Conversely, he has nothing but hate for Easy whom he feels stole Callie away from him. When Jenny Humphrey first arrives at Waverly, he is attracted to her, but is quickly disappointed when she first makes out with his horny roommate Heath Ferro, and later confesses to Brandon that she likes Easy. Nevertheless, Brandon remains a good friend to Jenny in spite of his perception that she has exceedingly poor taste in guys.
- Benny Cunningham, a horsey looking girl with brown hair and brown eyes, is a friend of Tinsley, Callie, and Brett. She is also Sage's best friend, but is crushed when she finds out that Sage is warming up to snobby Emily Jenkins. She comes from a very aristocratic background and is referred to as "American royalty."
- Isaac Dresden is the son of the new dean, Dr. Henry Dresden, and brother to Isla Dresden. He has dark wavy/curly hair, pale green eyes, and smooth, tanned skin. Like the rest of the It Girl cast, he is unbelievably gorgeous and rich. He immediately takes a liking to Jenny. Together with Jenny, he plans a party at the dean's house which went terribly wrong. Despite seeming sweet, he had some secrets.
- Isla Dresden is the daughter of the new dean, Dr. Henry Dresden, and sister to Isaac Dresden. Like her brother she has dark wavy hair and green eyes. Throughout the series, she goes from being Tinsley's best friend to her worst enemy. She tends to go to several different schools per semester due to her "high-spirited" behavior which includes having an affair with a Brad Pitt-like teacher at a school in Senegal. She loves to take risks and break the rules and takes advantage of her being a "daddy's girl" to easily manipulate her parents and others into giving her what she wants. She does her Jan Plan project with Tinsley which causes the two to become fast friends but the two have a falling out when Isla blames Tinsley for breaking an expensive stained glass window. She attempts to explain herself to Tinsley by claiming that if their situations were reversed, Tinsley would've done exactly the same thing. However, Tinsley disagrees and ends their friendship.
- Sage Francis is best friends with Benny Cunningham. Though initially thought to be just another ditzy, blonde, gossiping minion of Callie's but is revealed that she is very unpretentious and sweet. She has a crush on Brandon who finds out from Chole Marymount, Dean Marymount's niece. The two begin dating but Sage breaks up with him because Brandon is "too sweet" and "too feminine."
- Julian McCafferty; tall, very hot, blond, and with a penchant for wearing funky T-shirts, Julian is somewhat of a mystery to the other Waverly students. Despite being a freshman, he hangs out with the junior-year boys in his dorm, usually Heath Ferro and Brandon Buchanan. He doesn't talk about himself much. In Reckless, he kisses Tinsley Carmichael, but Tinsley insists that they keep their relationship a secret. Julian complies, but in Unforgettable he finds himself attracted to Jenny Humphrey, whom he often bumps into when hanging around Tinsley's dorm.
- Yvonne Stidder, a saxophone player and member of the Jazz Band with a slight British accent, is eager to join the in crowd, though she is generally ignored by the more important population of Waverly. Yvonne is the first girl Jenny meets at Waverly. In a game of I Never which kicks off most of the drama, Yvonne reveals that she is a virgin. Her house in New York is the main setting for Infamous, as she holds a party while her parents are away. She is known for her bad fashion sense and eagerness to boost her own popularity, which often fails dramatically and is laughed at by Tinsley and Heath especially.
- Alan St. Girard is the roommate of Easy Walsh. Notorious for smoking pot, and never shaving his beard. He and Easy spend their times together playing on his Xbox in their dorm room and he dates Alison Quentin but the two break up over Thanksgiving break due to the fact that Alan is planning on meeting up with an old pot-smoking girlfriend and cannot promise to be faithful. In the last book of the series Alan and Callie are paired as perfect match. While the two do not get involved romantically, Alan gives Callie advice on how to deal with her feelings for both Brandon and Easy which backfires.
- Sebastian Valenti; Brett has been ordered to tutor Sebastian in Tempted, the book in which he is introduced. He has shiny, long black hair which he puts gel in and has a New Jersey accent. He has 'cheekbones that you only see in Armani ads', an olive skin tone, and dark, almost black eyes. In Tempted, he lets Jenny and Tinsley borrow his car. In Infamous, he gives Brett a ride to her house during Thanksgiving break. They realize his best friend used to date Brett in 8th grade. They flirt, argue and tease each other often. Brett later invites him to Thanksgiving under false pretenses. He likes her tacky cropped black shirt and leopard print skirt and her family's animal print furniture, and bonds well with her parents. In Adored, he and Brett make a bet about whether he knows how to attract girls - Sebastian claims that if he changed his appearance and put on a polo shirt, girls would chase after him. He goes on a couple of dates with Callie, who tries to morph him into her ideal boyfriend, making Brett go into a jealous rage. She finally admits her feelings towards Sebastian as they kiss and get together at the end of the novel. In Devious Brett breaks up with him, after jumping into conclusions that he is talking to his past ex-girlfriends, only to be found later on that he was calling to tell them that he was off the dating market. He and Brett get back together in the end.
- Kara Whalen first makes an appearance in Reckless during a party held at Dumbarton. She becomes popular after throwing beer in Heaths face as revenge for teasing her when she was fat. Her mother is a fashion designer, which also contributes to her popularity. Sage, Benny and the others are known for wearing her clothes. In Unforgettable, Kara is having a rather close relationship with one of the Waverly girls and they keep it a secret until Callie reveals it during The Cinephiles party.