Jenna is a 16-year-old high school student who feels awkward and unsuccessful everywhere except at her job at Gladstone's Shoes, where she excels as a confident "shoe professional." At 5'11" with red hair, she struggles with her self-image and carries the heavy emotional weight of caring for her family. She is highly observant, driven by a need to help and protect those around her, and nervously accepts a summer job driving her elderly boss to Texas.

Mrs. Gladstone is the tough, 73-year-old president and CEO of Gladstone's Shoe Stores. The daughter of a Baptist minister, she built the company from scratch with her late husband and remains fiercely dedicated to high-quality merchandise. Suffering from a painful hip and facing a hostile corporate takeover from her own son, she hires Jenna as her personal driver to secretly inspect branch stores on the way to a Texas board meeting.

Jim is Jenna and Faith's father, a charismatic former traveling salesman who has been largely absent from their lives for over two years. His severe alcohol addiction dictates his erratic behavior, leading to unannounced visits and constant disappointment for his family. He refuses to accept his addiction, expecting his oldest daughter to cover for him.

Harry, known as "Mahatma Bender," is the legendary manager of the flagship Gladstone's store in Dallas. A recovering alcoholic with 23 years in Alcoholics Anonymous, he wears cowboy boots and a Stetson hat. He is deeply compassionate, dispensing vital life advice to Jenna while marshaling shareholder support to help save Mrs. Gladstone's company.

Elden is Mrs. Gladstone's only son and a major shareholder in Gladstone's Shoes. Dressed in floppy suits and tasseled Italian loafers, he is a corporate-minded executive who prioritizes cheap manufacturing and high profits over his parents' legacy of quality. He eagerly seeks to oust his mother from the company she built.

Jenna's grandmother is a former tailor who was known for her vibrant outlook and commanding physical presence. She now lives in a nursing home as she struggles with Alzheimer's disease. Before her memory began to fail, she was Jenna's best friend and primary source of strength, explicitly asking Jenna to help her remember as her condition worsened.

Carol is an emergency-room nurse who works long night shifts to support her two daughters as a single mother. She is fiercely independent and harbors deep resentment toward her ex-husband Jim for the chaos he brings. Despite her grueling schedule, she tries her best to stay involved and supportive of her girls, though she sometimes misses their deeper emotional struggles.

Alice is an elegant retired shoe model and Mrs. Gladstone's close friend of 41 years. Known for her crisp suits, dry humor, and no-nonsense attitude, she refuses to coddle Mrs. Gladstone, instead pushing her to fight for her health and company. She takes a maternal interest in Jenna, offering her fashion advice and boosting her confidence on the road.

Murray is a middle-aged, balding man who has been selling shoes for 23 years. As the manager of the Gladstone's shoe store in Chicago, he is a kind, patient boss who truly cares about quality and good service. He serves as an influential, supportive adult figure who builds up Jenna's self-confidence when she doubts herself.

Faith is Jenna's beautiful, 14-year-old younger sister. She has blonde hair and green eyes, and Jenna often compares herself unfavorably to her. Faith struggles with her father's lack of attention and relies heavily on Jenna to navigate the family's emotional turbulence, often feeling left out of the painful dynamics.

Ken is the 32-year-old CEO of The Shoe Warehouse, a rapidly expanding budget footwear chain. Known as the "Wall Street shoe baron," he is the executive Elden Gladstone wishes to merge with. Though initially viewed by Jenna as an enemy to quality, she learns he is a self-made man who started his career with a simple newspaper delivery route.

Opal is Jenna's best friend in Chicago. She works at a local Fotomat booth and provides a grounded, youthful connection for Jenna. She offers dramatic advice and supports her friend through her family difficulties and road trip anxieties.

Gladys is Grandma's roommate at the Shady Oaks Nursing Home. She is highly functional, friendly, and provides pleasant companionship for Grandma.

Floyd is Mrs. Gladstone's late husband. Together, they built Gladstone's Shoes from the ground up, instilling the core values of quality and customer care that define the company's ethos.

Miles is the manager of the Gladstone's Shoe Store in Peoria, Illinois. Hired by Elden, he runs a sloppy, poorly managed branch with an uneducated sales force, representing the exact decline in quality Mrs. Gladstone fears.

Mac is Elden Gladstone's loyal assistant in Dallas, tasked with enforcing Elden's directives and managing logistical elements like intercepting unwanted guests at corporate events.