Photo Diary: Olivia Holt Takes Us Backstage of Chicago on Broadway

Since its debut in 1975, the musical Chicago has been a beloved mainstay on Broadway—it currently holds the title for the longest active-running production—and the stylish shoes of its infamous murderess Roxie Hart have been filled by a slew of noteworthy names. Originally portrayed onstage by Gwen Verdon, the role has since been played by the likes of Liza Minnelli, Renée Zellweger (in the 2002 Oscar-winning film adaptation), Michelle Williams, Ashlee Simpson, Christie Brinkley, Pamela Anderson, and Angelica Ross, to name a few. 

Taking up the torch in its current run is actress and singer Olivia Holt. The 25-year-old, who starred in last year’s hit series Cruel Summer, kicked off her eight-week engagement at the Ambassador Theatre on April 10, taking on favorite musical numbers "Funny Honey” and "Roxie.” The performance marks Holt’s Broadway debut and a thrilling one at that. So before the curtain falls on her final June 4 show, we asked the actress to document a typical day in the life playing one of the most iconic stage characters.


(Image credit: Olivia Holt)

"I start the day with a walk and a yummy oat milk latte that I usually end up taking to go to the theatre.”


(Image credit: Olivia Holt)

"I start my skin prep using Shani Darden’s Weightless Oil-Free Moisturizer ($48) and serum and Sonya Dakar’s Blue Butterfly Balm ($85).”


(Image credit: Olivia Holt)

"Then I go in with some light foundation using Koh Gen Do foundation and Nars concealer and fill in my brows with Anastasia Beverly Hills Brow Wiz Ultra-Slim Precision Brow Pencil ($25) in Taupe. I begin my smoky eye with Makeup by Mario Master Mattes Eyeshadow Palette ($50) and Dusty Rose Blush ($30).”


(Image credit: Olivia Holt)

"Our wonderful hairdresser Barry getting me wig ready!”


(Image credit: Olivia Holt)

"Roxie’s little black wardrobe.”


(Image credit: Olivia Holt )

"Along with some fun shoes…”


(Image credit: Olivia Holt )

"A quick warm-up and stretch before I get dressed for act one.”


(Image credit: Olivia Holt )

"It’s officially showtime!”

Catch Olivia Hart in Chicago on Broadway from now until June 4. 

Executive Director, Entertainment

Jessica Baker is Who What Wear’s Executive Director, Entertainment, where she ideates, books, writes, and edits celebrity and entertainment features.