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, in Lily's eyes it lacks a certain chic, and thus is but one step away from dinginess. 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. Mrs. Peniston took pleasure in the public display of her generosity by agreeing to take Lilly on for a year after her mother died—much to the relief of the extended family. Lily stayed on for years because she was able to adapt to her aunt's passive ways and because Mrs. Peniston was indulgent for the volatility of youth. Lily is dissatisfied with her existence in her aunt's house to the point of engaging in "fits of angry rebellion against fate"(56). She desires to make an independent life for herself, but that is economically and socially impossible. The peaceful co-existence she has constructed with her aunt comes to an end when Mrs. Peniston hears the rumors that Lily has had an affair, learns that Lily gambles on Sundays, and then disinherits her leaving Lily without a fashionable place to live and without a substantial inheritance.
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.
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 turns sour and Lily commits to repaying her debt to Gus rather than to bestow him with the sexual favors he desires.
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 money.
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.
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. In Book Two, she becomes one of Lily's only friends, giving her a place to stay and taking care of her when everyone else abandons her.
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. Jack has business dealings with Sim Rosedale and has tried to afford him entré into New York's high society. 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 competitive middle-aged cousin who lives in a boarding house and who attracts and remembers all manner of gossip related to high society in general and to Lily in particular. Unbeknownst to Lily, Grace dislikes her because she felt "mortally offended" at being excluded from her Aunt Peniston's dinner party for Jack and Gwen on their return from their honeymoon. She surmised, not unjustly, that it was Lily's counsel to her Aunt Peniston that kept her from being included. To get even Grace relays to Aunt Julia the talk about Lily's attention to Gus Trenor in exchange for money that Lily used to pay gambling debts. Grace refuses to give Lily financial assistance when she is down and out.