When people talk about the modern "it" girl, Olivia Culpo is usually the first name that pops up. But before she was the face of every major fashion house or the wife of NFL star Christian McCaffrey, she was a Rhode Island girl with a massive dream: landing a spot in the Sports Illustrated Swimsuit Issue. Honestly, most people think it just happened because she was Miss Universe. It didn't.
The industry is brutal. Olivia had to fight for her spot in the magazine just like everyone else. She actually spent years building a portfolio and taking test shoots before the editors finally gave her the nod.
The Raw Truth of the Olivia Culpo Sports Illustrated Journey
Most fans assume Olivia’s first shoot was a glamorous beach day. It wasn't. In 2018, her debut wasn't even in a swimsuit. It was for the "In Her Own Words" project. She was in a studio in Brooklyn, not some tropical island.
She had words like "Beauty is not perfection" and "Stand in your truth" painted across her body in black ink. It was vulnerable. It was gritty. It was about reclaiming the female narrative before the #MeToo movement fully took over the headlines.
The 2020 Cover That Changed Everything
If you were online in July 2020, you couldn't escape the cover. Olivia Culpo, Kate Bock, and Jasmine Sanders—the "Golden Trio"—posed in Bali. This was the moment Olivia finally reached the peak.
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- Photographer: Yu Tsai.
- Location: Bali, Indonesia.
- The Vibe: High-fashion tropical.
But here's the thing. They wrapped that shoot on March 5, 2020. Literally days before the entire world shut down. While we were all stuck at home in sweatpants, those images were the last bit of "normal" glamour we had.
Olivia didn't just have one cover; she had a solo one too. She wore a tiny black Minimale Animale suit that became an instant bestseller. The impact was huge. She wasn't just a model anymore; she was a brand.
Why Olivia’s SI Run Was Different
Usually, models do one or two years and move on. Olivia stayed. She came back in 2019 for a shoot on Kangaroo Island in Australia. Then again in 2021 in Hollywood, Florida.
What made the 2021 shoot stand out was the "Old Hollywood" aesthetic. Photographer Ben Watts captured her in these vibrant, retro-inspired pieces. It felt different from the 2018 Brooklyn shoot. It was more confident. More "WAG" chic, as she was already dating McCaffrey at the point.
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Breaking Down the Wardrobe
Olivia’s style in the magazine evolved constantly. In Australia, it was all about crochet. She wore multiple neutral-toned knit pieces that made the rugged landscape of Kangaroo Island look soft.
By the time she got to Florida in 2021, she was rocking:
- Norma Kamali (bold, structured)
- Anna Kosturova (detailed knits)
- Rudi Gernreich (geometric and sporty)
She’s basically a chameleon. She can go from "girl next door" in a white bikini to "high-fashion editorial" in a mesh one-piece without breaking a sweat.
The "Secret" to Her Success
MJ Day, the editor-in-chief of SI Swimsuit, has said on record that Olivia is one of the hardest-working people in the game. She doesn't just show up and look pretty. She’s a "multi-hyphenate."
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She’s a restaurateur (she owns Back 40 in Rhode Island). She’s a philanthropist who started "More Than A Mask" during the pandemic. She’s an actress. Basically, she used the Olivia Culpo Sports Illustrated platform to launch a legitimate business empire.
Life After the Cover
Fast forward to 2026, and Olivia is in a whole new chapter. She and Christian McCaffrey recently welcomed their daughter, Colette Annalise, in the summer of 2025. You’d think she’d slow down, but she’s already back to work, hosting Next Gen Chef and appearing in the SI 60th Anniversary "Legends" features.
The magazine has changed too. It's more about "who you are" than "what you look like." Olivia was one of the first models to really lean into that, sharing her struggles with endometriosis and the pressures of the industry while still looking like a goddess on the cover.
Actionable Insights for Aspiring Creators
If you’re looking at Olivia’s career and wondering how to replicate even a fraction of that success, here’s what you need to do:
- Diversify Early: Don’t just be a "model" or a "writer." Build a brand that touches on different industries. Olivia’s restaurant and clothing lines gave her staying power when modeling jobs were lean.
- Authenticity Wins: People connected with her 2018 "In Her Own Words" shoot because it felt real. Don't be afraid to show the "behind the scenes" messiness.
- Leverage Every Platform: Olivia used her Miss Universe win to get into SI, and she used SI to get into acting and hosting. Each win should be a stepping stone, not the destination.
The Olivia Culpo Sports Illustrated story isn't just about a girl in a bikini. It's about a woman who knew exactly what she wanted and worked for a decade to make sure she wasn't just a face on a page, but a name you couldn't forget.
For more on how the modeling industry has shifted toward influencer-led brands, you can check out the latest industry reports from The Society Management or follow the SI Swimsuit official archives for 2024-2026.