Lily Bart—Wharton paints Lily, the heroine of her novel, as a complex personality with the purity that her Christian name implies, the defiance that her surname implies,[m] and the foolishness that the title of the novel implies. The combination of the social pressures and conventions of her reference group and her refusal to "settle" numerous times to save herself portend a fateful destiny where she becomes complicit in her own destruction. Wharton depicts Lily as having an aesthetic purpose in life—a fine specimen to be looked at and admired. Her extraordinary beauty should have served her well to find a wealthy husband with the requisite social status that would have secured her place in upper-class New York society. However, her inner longing to become free of her society's social conventions, her sense of what is right, and her desire for love as well as money and status have thwarted her success in spite of a number of eligible admirers over the ten years she has been on the marriage market. Challenges to her success are her advancing age—she is 29 as the novel begins—the loss of her father's wealth, and the death of her parents which has left her orphaned without a caring protector, her constant efforts to "keep up with the Joneses"(4),[n] the very modest but erratic "allowance" from her straight-laced Aunt Julia, and her gambling debts which make her the subject of vile gossip. To protect Lawrence Selden's reputation, she refuses to use damning evidence against her nemesis, Bertha Dorset, which would have recouped her ruined social standing. This leads to a tragic yet heroic ending.
Lawrence Selden—A young lawyer who, although not wealthy himself, is able to move easily within and without Old New York's elite social circles through kinship with old-line New York families. He has known Lily since her "coming out" eleven years earlier. For all this time he has been in the background of her life. He views the comings and goings of New York's high society with the detachment and the objectivity of an outsider —a characteristic that Lily not only admires but also that allows her to view those people in her surroundings in an objective, critical and a not-so-flattering way. She becomes fascinated and envies his independence from the "tribe" and the freedom that has given him.[o] Her encounters with Selden underscore the conflict between her inner voice —her self-hood at its core— and the outer voices of her reference group. It is from Selden's description, assessment and admiration of Lily's outward characteristics that we glean those attributes that contribute to New York high society's perception and misperceptions of who she is. He can be brutally honest about Lily's superficiality and artificiality and simultaneously appreciate the sparks of freedom and spontaneity that temper these negatives. These mutual admirable qualities give way to their romantic regard for one another. He is not, however, free from the social pressure of rumor. Though he has shown Lily consistent friendship, he abandons her when she becomes the victim of appearances that put her virtue, as an unmarried woman,in question.
Simon Rosedale—A successful and socially astute Jewish businessman—the quintessential parvenu—who has the money but not the social standing to be accepted into the circle of New York's leisure class. Building his fortune in real estate, Rosedale makes his first appearance in the story when he observes Lily leaving his apartment building after what appears to be a tryst with one of his tenants. Rosedale is interested in Lily because not only is she beautiful, but what is more important, she is also a social asset in gaining him a place in high society. She reflects that she has put herself in his power by her clumsy dress-maker fib and her refusal to allow him to take her to the station which would have given him the prestige of being seen by members of the society with whom he was aspiring to gain acceptance. As his social ascendency continues, he offers Lily marriage which would provide her a way out of her financial dilemma and her precarious social standing; she puts him off. His cleverness and business acumen serve him well to achieve a higher and higher rung on the social ladder. Lily, however, is on her way down to the point that Rosedale is no longer interested in marrying her. Despite the differences in their social standing , Rosedale by the end of the story shows compassion for Lily. He offers her a loan when he runs into her after she has lost her hat-making job—an offer she refuses.
Percy Gryce—A conservative, rich, but shy and unimaginative young eligible bachelor on whom Lily, with the support of her friend Judy Trenor, sets her sights. Percy's less than titillating personality notwithstanding, Lily works out a strategy to catch him at week-long festivities at Bellomont. Her fortuitous and successful encounter with Percy on the train to Bellomont further encourages her in pursuit of her goal. Her strategy gets interrupted, however, when Selden at week's end also appears on the scene unexpectedly. Lily then decides, on the spur of the moment, to set aside her well-thought-out tactics to pursue Percy in favor of spending some time with Selden. When, at a more rational moment, she returns to pursuing Percy, his mother-in law-to-be tells Lily at Jack Stepny's and Gwen Van Osburgh's wedding about his engagement to Evie Van Osburgh.
Bertha Dorset (Mrs. George Dorset)—A petite and pretty high-society matron whose husband George is extremely wealthy. She is first introduced catching the train to Bellomont where she boards with great fanfare and commotion. She demands that the porter find her a seat with her friends, Lily and Percy. Once at Bellomont Judy Trenor intimates to Lilly that Bertha is manipulative and also unscrupulous such that it is better to have her as a friend rather than an enemy. It is well known that Bertha is bored with her husband and seeks attention and love outside the confines of marriage. At Bellomont Bertha continues to pursue Selden in an attempt to rekindle the flame of an adulterous affair they have been carrying on but with which he has become disenamored. As Book I ends, she invites Lily to accompany her on a Mediterranean cruise to distract her husband so she can carry on an affair with Ned Silverton. Bertha understands, as a married woman, she must keep up appearances and ruthlessly impugns Lily's reputation to mask her own adultery. She spreads false rumors that besmirch Lily's virtue among their friends. Lily, as an unmarried woman without a protector, has little she can do in her own defense.
Mrs. Peniston (Julia)—Lily's wealthy, widowed Aunt –sister to Lily's father. Mrs. Peniston embodies "old school" morality and has a family pedigree that goes back to the industrious and successful Dutch families of early New York. Although she maintains an opulent residence on fashionable Fifth Avenue, she does not follow fashion or renovate constantly to maintain a chic appearance. In Lily's eyes, the Peniston home is therefore dingy. Mrs. Peniston's "Old New York" lifestyle requires keeping her drawing room neat, eating well and dressing expensively. She harbors a passive attitude and does not actively engage in life. Although she spends time in the country during the first part of the book, by the last half of the book she is a shut-in with significant heart problems. When Lily arrived in New York in financial distress after the death of her mother, Mrs. Peniston took pleasure in the public display of her generosity by agreeing to take Lily on for a year after her mother died—much to the relief of the extended family. She found, to her surprise, that she liked the volatile Lily. She therefore continued to support Lily for over a decade during Lily's fruitless search for a wealthy, socially connected husband. She indulges and passively enables Lily's habit of gallivanting with her fashionable friends, and ignores the way Lily avoids and abandons her. Although Lily is clearly Julia's favorite, displacing her previous favorite Grace Stepney, Julia never makes any verbal or written promise to provide for Lily in the long term. Although Lily and her friends believe that is "understood" that she will inherit most if not all of Julia's fortune, Julia herself never made such a statement. Indeed, her forbearance is stretched to the limit when rumors reach her that Lily gambles for money and is encouraging attention from married men who compensate her for it. As upset as Julia is by evidence of Lily's immoral behavior, she does not immediately ask Lily for details because it is easier to discredit the messenger. When Lily comes to Julia asking for money to pay various debts, including what Lily passes off as gambling debts, Julia refuses. The relationship is permanently damaged, and when Lily sails away with the Dorsets instead of cleaning up the social and financial mess she has made, Julia does not write to Lily or attempt to repair the relationship. When word reaches her that Lily has been publicly accused of having an affair with George Dorset, and when Lily continues to gallivant in Europe instead of returning home, Julia disinherits Lily in favor of the more loyal Grace Stepney. By the time Lily returns to New York, Julia has died, and nobody knows about the disinheritance until her will is read.
Judy Trenor (Mrs. Gus Trenor)—Lily's best friend and confidante— is the stereotypical high-society matron, married to Gus Trenor, a successful business man. She frequently hosts large parties and social events at their country home, Bellomont. By engaging in gossip Mrs. Trenor keeps up on the social scene. She acts as matchmaker between Lily and Percy Gryce. She uses Lily as her surrogate private secretary and spends much of her day making sure that every detail of her events is done to perfection. This includes poring over lists to decide which guests are the most desirable to invite, which have been "stolen" by another conflicting event, and which unmarried men and women should be set up together. She invites Selden to Bellomont on anonymous advice to keep Mrs. George Dorset entertained. Judy suffers from frequent headaches and avoids noisy environments such as the opera. She must sometimes cancel minor engagements on short notice, and prefers to stay at Bellomont when her head hurts.
Gus Trenor—Judy Trenor's husband—a massive man with a heavy carnivorous head and a very red complexion. He is a successful stock market speculator and an advocate of Sim Rosedale's acceptance in high society circles although he considers him a bounder. He is also a notorious flirt and looks for attention in relationships with women outside of his marriage. Gus becomes enamored with Lily, a frequent guest at his wife's weekend social events. He uses his financial investment skills and a large sum of his own money in a risky investment for Lily which she agrees to. The proceeds from this speculation will help her pay her gambling debts and other expenses necessary to keep up appearances. The investment pays off for Lily financially, as Gus intends that it should, but the friendship turns sour when Lily is unwilling to exchange romantic attention for money the way Gus believes she tacitly agrees to do.
Carry Fisher (Mrs. Fisher)—A small, fiery and dramatic divorcée. She is perceived as carrying "a general air of embodying a 'spicy paragraph';"(70) and according to Mrs. Trenor, ". . .most of her alimony is paid by other people's husbands." (91) She sponges money from Gus Trenor to cover her bills much to his wife's chagrin. Although Gus accepts romantic favors from Mrs. Fisher in exchange for paying her bills and investing her money in the stock market, he considers her a "battered wire-puller"(94) in comparison to the fresh and unsullied Miss Bart. Carry is also known for bringing newcomers into high society such as Rosedale and the Welly Brys who had managed the miracle of making money in a falling market. After Lily has been expelled from the upper class by Bertha, Carry is one of the few people who still shows compassion toward her, offering Lily support and job opportunities. Carry is an example of a woman who finds ways to earn money and to succeed in society despite being divorced and somewhat disreputable. Her presence in the story refutes the notion that Lily has no choice except to self-destruct.
Ned Silverton—A young man, whose first intention was to live on proofreading and write an epic, but ended up living off his friends. Ned's romantic relationship at the Bellomont house party is with Carry Fisher. Six months later Ned accompanies Lily and the Dorsets on their Mediterranean cruise. He has an affair with Mrs Dorset, who manages to keep it concealed from most of society. Ned's increasing gambling addiction consumes not only his resources but that of his sisters, who live in poverty while he travels with Bertha Dorset. After the fling with Bertha ends, Ned participates in a scheme to help a purportedly wealthy but disreputable woman to marry the younger brother of Gwen and Evie Van Osburgh. This conspiracy, in which Lily is implicated, helps ensure Lily's downfall.
Evie Van Osburgh—A young, innocent, dull, and conservative, stay-at-home kind of a girl, heiress to a substantial fortune. Judy Trenor paired her sister, Gwen, with Percy Gryce at the Sunday-night supper at Bellomont. Evie ends up getting engaged within six weeks of their stay at Bellomont to Percy Gryce due to Bertha Dorset's match-making skills.
Gerty Farish—Selden's cousin. She is a kind, generous woman who occupies herself with charity work, but Lily despises her because of her less than glamorous appearance. In Book Two, Gerty becomes one of Lily's only friends, giving her a place to stay and taking care of her when everyone else abandons her. Lily does not wish to continue living with Gerty or combining resources because she is unwilling to lower herself to the standard of living Gerty can afford.
Jack Stepney and Gwen (Van Osburgh) Stepney—A very wealthy couple—guests at Bellomont just before celebrating their wedding at the Van Osburgh's estate six weeks later. They belong to Old New York's high society although their money comes from Gwen's side. Prior to his marriage, the nearly bankrupt Jack has business dealings with Sim Rosedale and has tried to afford him entré into New York's high society. After marrying Gwen, Jack becomes plump, conservative, and complacent. Jack is Lily's cousin so he agrees to shelter her for the night after Bertha kicks her off her yacht for ostensibly carrying on romantically with Bertha's husband.
Grace Stepney—Lily's middle-aged cousin lives in a boarding house and has spent most of her life waiting on Julia Peniston. Until Lily arrived, Grace was Julia's favorite: she shares Julia's conservatism and sense of propriety, and she is willing to help out during the fall cleaning. Grace attracts and remembers all manner of gossip related to high society in general and to Lily in particular, but does not generally gossip herself. Lily treats Grace very poorly, regarding her as insignificant. When Lily prevails on her aunt Julia to exclude Grace from a family dinner party, Grace retaliates. She relays to Aunt Julia the talk about Lily's attention to Gus Trenor in exchange for money that Lily used to pay gambling debts, and stops protecting Lily from the otherwise predictable consequences of Lily's actions. When Lily comes to Grace after the reading of the will, Grace does not have the money to give Lily the loan she is asking for because the assets Grace inherited from Julia are still tied up in probate. When Lily asks Grace to borrow money against Aunt Julia's estate and lend or give it to Lily, Grace refuses.