- Adam Chanler-Berat - Jordan Glassberg
- Zión Moreno - Luna La
- Jason Gotay - Rafa Caparrós
- Savannah Lee Smith - Monet de Haan
- Todd Almond - Gideon Wolfe
- Megan Ferguson - Wendy Fineman-Walsh
- Sarah Baskin - Rebecca Sherman
- America Olivo - Martine
- Kelsey Lu - Kelsey Lu
- Gary Littman - Doctor
- Cedric Cannon - Store Owner
- Rana Roy - Reema
- Paul James - Aaron
- Erin Lindsey Krom - Linda Schacter
- Douglas Everett Davis - Henry Schacter
- Jakob von Eichel - George
- Ann Harada - Linda
- Frank DiLella - Frank DiLella
- Oskar Eustis - Oskar Eustis
- Azhy Robertson - Milo Sparks
- Princess Nokia - Princess Nokia
- Yoko Hyun - Shika
- Mason Versaw - Simon Ravetch
- Jared Reinfeldt - Victor
- Yin Chang - Nelly Yuki
- Billy Porter - Singer
- Marc Shaiman - Pianist
- Tamara Fay - Celeste
- Carla Hall - Rocky
- Elisabeth Waterston - Lara
- Shari Abdul - Maya
- Jason Liebman - Dr. Gibson
- Hettienne Park - Jodi Menzies
- Lucy Punch - Saskia Bates
- Alexandra Chelaru - Valeria
- Lyne Renee - Helena Bergmann
- Malcolm McDowell - Roger Menzies
- Alisyn Camerota - Alisyn Camerota
- April Hernandez Castillo - Carmen Gruben
- Jenna Leigh Green - Nancy Vogel
- Katerina Tannenbaum - Riley Love
- Sejal Joshi - Rachel
- John Benjamin Hickey - Roy Sachs
- Donna Murphy - Vivian Burton
- Elizabeth Lail - Lola Morgan
- Jeremy O. Harris - Jeremy O. Harris
- Edmund Donovan - Scott Kovacs
- Aaron Schwartz - Vanya
- Zuzanna Szadkowski - Dorota Kishlovsky
- Wallace Shawn - Cyrus Rose
- Margaret Colin - Eleanor Waldorf
- Nate Washburn - Micah
- Aubin Bradley - Ana
- Serena Berman - TA
- Ella Rubin - Bianca Breer
- Katherine Reis - Pippa Sykes
- Cole Doman - Rex Huntington
- Jonathan B. Wright - Klaus
- Kathryn Gallagher - Heidi Bergmann
- Ann Magnuson - Donna Calloway
- Peter Grosz - Mr. Spencer
- Jeanette Bonner - Payton Sykes
- Stacey van Gorder - Barrett Brier
- Maya Rosewood - Personal Shopper
- Amanda Warren - Camille de Haan
- Mitchell Slaggert - Rob
- Luke Kirby - Davis Calloway
- Tanis Parenteau - Samantha
- Carla Brandberg - Gerta
- James Wilcox - Kenneth
- Dean Neistat - Bouncer
- Carol Jacobanis - Mom
- Grace Dumdaw - Popular Girl
- Robyne Parrish - Twin Mom
- Rina Mejia - Rosa
- Max Garfin - Jock Teen
- Kristen Bell - Gossip Girl (voice)
- Pico Alexander - Mike Shubin
- Anna van Patten - Grace Byron
- Lois Smith - Iris Lefferts
- Bryan Terrell Clark - Garrett Barnes
- Artrece Johnson - Gwen Barnes
- Grace Lee - Spectator Rep
- Hunter Harris - Hunter Harris
- Rick Worthy - Greyson de Haan
- Julie Halston - Sharon
- Julie Halston - Sharon Kleinberg
- Samantha Rose Baldwin - Shelby Wright
- Angelic Zambrana - Tati
- Angelic Zambrana - Tati Gardinier
- Allie Levitan - Anne-Marie
- Gretchen Allison - Chairwoman Stroud
- Brenda Currin - Chairwoman Hartshorn
- Elizabeth Stanley - Charlotte Byron
- Frank Whaley - Mr. Keller
- Ana Yi Puig - Tiff Myers
- Henry Trueheart - Luc
- Winslow Bright - Head Teacher Duvall
- Ariel Eliaz - Sergeant
- Erin West - Erica
- Roya Shanks - Odeon Hostess
- Haniq Best - Budtender
- Charli XCX - Charli XCX
- Renée Stork - Barbara Shubin
- Michelle Trachtenberg - Georgina Sparks
- Sandra Maren Schneider - Daniela Sommer
- Sandra Maren Schneider - Daniela
- Zephani Idoko - Ashley
- Orfeh - Orfeh
- Ali Stroker - Ali Stroker
- Andy Karl - Andy Karl
- Dash Mihok - Richard Hope
- Aaron Quinn Long - Florian
- Johanna Braddy - Jessica Bradley
- Fernanda Urrejola - Dolores
- Miriam Cruz - Yoli
- Yên Sen - Young Woman
- Adam Enright - Florist
- Francesca Ferrara - Hotel Maid
- Leighton Samuels - Rhinebeck Waiter
- Delilah Napier - Taylor
- Adam Keane - Partygoer
Lois Smith interpreta a Iris Lefferts en la serie.
Whitney Peak interpreta a Zoya Lott en la serie.
Tavi Gevinson interpreta a Kate Keller en la serie.
Eli Brown hace el papel de Obie Bergmann.
Thomas Doherty hace el papel de Max Wolfe.
Emily Alyn Lind interpreta a Audrey Hope en la serie.
Evan Mock hace el papel de Aki Menzies.
Johnathan Fernandez hace el papel de Nick Lott.
Laura Benanti interpreta a Kiki Hope en la serie.
Adam Chanler-Berat interpreta a Jordan Glassberg en la serie.
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