At 28, Molly Sims Was Gearing Up To Wear A $30 Million Diamond Bikini

In 2001, Molly Sims was 28 and living her best life, hosting MTV’s House of Style, walking the Victoria’s Secret Fashion Show, and starring on the cover of Sports Illustrated. “Twenty-eight was fun,” she says.

Born in Kentucky with a passion for politics, Sims went to Vanderbilt University intending to become a lawyer. There, at the suggestion of her roommate, she snapped a few pictures. The future model signed with Next Management after her first meeting.

Suddenly, she was on a wild ride: Runways and photoshoots brought her all over the world. She began to pursue big-screen acting dreams in Hollywood while maintaining “real-life” friendships in NYC. “I took 77 red-eye flights between New York and L.A. during that time,” Sims says.

Sims says she wasn’t an obvious choice for the cover of SI. “I had more of an athletic look,” she says. “It was the best feeling for a girl like me.” The model was featured in SI another four times. In one 2006 issue, she famously sported a $30 million diamond bikini — the magazine’s most expensive suit to date.

Her acting career took off, too, as she played the brilliant Delinda Deline on NBC’s comedy-drama Las Vegas from 2003 to 2008. Today, she hosts the cheeky beauty podcast Lipstick on the Rim and founded the innovative skin care brand Yse Beauty (pronounced “wise”) in 2023. “I’ve lived nine lives,” Sims reflects.

Below, the multi-hyphenate discusses behind-the-scenes of life in Hollywood at 28, beauty, and the dating advice she’d give her younger self.

Take me back to the early aughts when you were 28. What were you doing? Where were you living?

Twenty-eight was a big year for me. I went from living in Paris and New York to L.A. more full time. The transition from modeling, to hosting, to acting was a major shift in my life.

What was your skin care routine at 28 compared to now?

I have always used micellar water, especially to take off my makeup after working all day. I also started to develop cystic acne at that time, so skin care was really important to me. I even was using Proactiv a bit for that, but reverted back to being a French pharmacy girl at heart: La Roche-Posay, Avène, Biologique Recherche Lotion P50 1970. I burned my face off from overusing P50 [a chemical exfoliant toner] back then, so it actually inspired me to create our [Yse Beauty] version of it called the Ex Pads.

What was it like being on the cover of Sports Illustrated?

That moment was life-changing for me, because it put a name with the face. Before that, models just had a face, and [I] didn’t even really have a name that was recognized.

What is a beauty product you used at 28 that is still in your makeup bag now?

I have used Vaseline on my eyelids forever for a dewy look. That and a white eyeliner on the waterline — I like Benefit Cosmetics — and Clinique waterproof mascara on your bottom lashes to finish. It will not budge.

What are your favorite products today?

I am obsessed with our new hydrating lip mask from Yse Beauty right now. It’s all the benefits of a mask, balm, and gloss in one product. The Skin Glow SPF is my go-to for skin prep, and the Vacation Highlighter to top if off.

What was dating like at 28?

I was always in a monogamous relationship of sorts, a bit codependent too. I was always attracted to the dead bird on the side of the street that you think you can save but you can’t.

What dating advice would you give to yourself then?

If you end up in therapy and you’re not married yet, it’s probably not going to work.

If you were to give one piece of advice to your 28-year-old self, what would it be?

Say yes. As hard as it is to change, do it. Change the job. Move. Dump the boy.

This interview has been edited and condensed for clarity.