Marge gets an expensive "new" dress at the outlet mall. While wearing it she meets a former schoolmate who invites her and the family to the country club. Marge becomes obsessed with trying to fit in. Homer takes up golf at the club and Mr. Burns challenges him to a game. After Homer catches him cheating, Mr. Burns agrees to help Homer's family become members of the country club if he doesn't tell anyone.
When Grampa Simpson tries to "fix" the family's television, it breaks irreparably, so the family travels to the Ogdenville outlet mall. Marge and Lisa wander off to a discounted store and Marge locates a beautiful Chanel suit, which has been marked from $2,800 and is now $90. Marge is first reluctant to buy the suit, but after Lisa's convincing that it's a great buy, Marge purchases the suit. She becomes infatuated with it and wears it constantly, begging Homer to take her somewhere fancy so the suit can be put to good use. However, one day when Marge wears it to the Kwik-E-Mart, she runs into an old classmate, Evelyn Peters. Evelyn is impressed by Marge's fashion sense and invites her to come to the Springfield Country Club (even though Marge has married Homer, as Evelyn originally assumes with horror). Marge, intimidated by the wealthy club members during a game of croquet, works hard to fit in with their snobbish ways. Along the way, Marge loses interest in her family and becomes obsessed with both impressing the club members and altering her suit so she comes off as wealthy.
Meanwhile, the rest of the family is uncomfortable at the country club until Lisa finds the stables and Homer begins playing golf. Homer is revealed to have a knack for golf, and Mr. Burns, having seen Homer's skill in the bathroom at work, challenges him to a match. Mr. Burns believes that he is the best golfer in Springfield, and is determined to take down Homer. However, once they begin playing, Homer, who is in disbelief at one of Mr. Burns' shots, runs over to the green and finds Mr. Smithers replacing the ball Mr. Burns hit with a new one that is close to the hole. Homer wants to reveal the cheating to the entire club, but Burns threatens to block the Simpsons' membership if he tells. Homer reluctantly agrees.
In the meantime, Marge is offended by a crack made by one of the snobby club members and is eager to change the suit even more to impress at a party. However, due to Lisa's annoyingly inquisitive nature, Marge accidentally destroys the suit on the sewing machine. She rushes back to the Ogdenville outlet mall, but there are no suitable clothes for the party. Marge, having nowhere left to turn, goes to the actual Chanel store and purchases a $3,300 dress. When she and the rest of the Simpsons arrive at the party, Marge criticizes the behavior of everyone in her family, including Maggie. Homer tells Marge that he and the kids will be silent and just stand in the corner the whole night so she can have a nice time. Marge realizes that she has changed for the worst, and goes to Krusty Burger with her family instead of the party. However, it is later revealed that the party was actually supposed to be an initiation party, as Evelyn Peters has decided to sponsor their membership.