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.
"I start the day with a walk and a yummy oat milk latte that I usually end up taking to go to the theatre.”
"I start my skin prep using Shani Darden’s Weightless Oil-Free Moisturizer ($48) and serum and Sonya Dakar’s Blue Butterfly Balm ($85).”
"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).”
"Our wonderful hairdresser Barry getting me wig ready!”
"Roxie’s little black wardrobe.”
"Along with some fun shoes…”
"A quick warm-up and stretch before I get dressed for act one.”
"It’s officially showtime!”
Catch Olivia Hart in Chicago on Broadway from now until June 4.

Jessica Baker has 16 years of experience in the digital editorial fashion and entertainment space. She is currently the Executive Director, Entertainment at Who What Wear where she ideates, books, writes, and edits celebrity and entertainment features.
-
These Luxe Nail Designs Are Begging to Be Worn With a Glitzy Dress This New Year's EveNew goals, new nails.
-
I Gave My Beauty Routine a Sophisticated Edit This Winter—17 Products That Whisper "She's Expensive"You'll see why.
-
Dua Lipa's Starry-Night Nails Just Made It to #1 on My List of Ideal NYE Party ManicuresThe disco-coded design screams December 31.
-
Every Chic Individual Is Wearing "Goth Christmas" Nails Right Now—6 Vampy Sets I'm Currently Obsessing OverElevated, not Ebenezer.
-
PDRN Skincare, Espresso Hair, and Polka-Dot Nails: 9 Trends That Dominated 2025, According to Search DataAs demonstrated by Hailey Bieber, Dua Lipa, and J.Lo.
-
Under-Requested Yet Highly Elegant: I'm Putting Gingerbread Nails at the Top of My Holiday To-Do ListI'm all about this warm, melty, molasses-colored mani.
-
It's Official: '80s Nails Are Back—17 Fashion-Forward Designs Giving This "Dated" Trend New LifeOh, the glamour!
-
Chrome French Manis Are Everywhere—10 Elevated Takes to Text to Your Nail TechWe're already wearing them.

