Clad in biker chick-meets-Mother Earth ensembles, supermodel Cindy Crawford, at 53, is still riding high at the top of her game.

Portrait of Tammy Strobel
Cotton jacket; knit bra; silk dress (worn as skirt); metal earrings; rope belt; leather boots, Dior
My Reading Room

Leather dress; leather belt, Alexander McQueen. Gold and diamond earring, Ana Khouri. Leather boots, What Goes Around Comes Around Vintage.

OPPOSITE: Silk fringe hoodie; metal earrings, Dior 
My Reading Room

When Cindy Crawford announced she was intending to move on from modelling ahead of her 50th birthday three years ago, it made front cover news. Such is the power of this beauty with the trademark mole.The rumours turned out to be somewhat exaggerated. She’s back on our cover looking as fit and fabulous as she ever was. She is possibly the first of her supermodel coterie (ie Supers Naomi, Christy, Claudia and Linda et al) to have successfully parlayed her modelling fame into Cindy Inc, building an empire ranging from skincare to home design. The matriarch of her own modelling clan—her two children, Presley, 20, and Kaia, 18, are fashion superstars themselves—now has the freedom to pick and choose her projects. The OG Super takes a few minutes out of her busy schedule to answer our questions.

Tell us about your first cover shoot for Harper’s BAZAAR Singapore.

It was in December 2005. I was in Kuala Lumpur, Malaysia, in my role as an OMEGA ambassador. The watch brand asked me to do a shoot as part of my schedule there. I remember arriving at Carcosa Seri Negara and I instantly connected with Kenneth Goh, the editor-in-chief, as well as Simon Upton, the photographer. It was such an elegant story and we loved shooting together!

How do you keep looking and feeling fabulous after more than 30 years in the business?

Thanks—I do try! I exercise, try to eat right and take care of my skin, but the most important thing is having gratitude and doing things that make you feel good: like living your work, connecting with friends and family, and giving back. 

What is your advice to new models?

This is such an exciting time in the modelling industry and I have a front row seat watching my daughter Kaia’s career. Some of my advice is the same as it would be for any job—be on time, be prepared and stay off your phone! But specifically for modelling, authenticity is even more important now than ever. As the fashion industry embraces diversity, social media gives everyone a platform to speak their truth and share what’s important to them. 

Is there one thing that you want to forge in this new decade?

My focus will be more and more on balance and being of service. My children are nearly grown, but I know I still have a lot to give. Finding new ways to share my gifts is what excites me!

Who are the fabulous women who inspire you? Who is your real-life hero?

More than anyone else, my mother inspires me and is my hero. She lost a child, my little brother Jeff, to leukemia and also went through a bad divorce from my father. But she remains the type of woman who chooses to see the best in everything and everyone.
My Reading Room

Leather dress, Bottega Veneta. Metal earrings, Ana Khouri. Metal necklace, Jenny Bird

OPPOSITE: Leather jumpsuit, Chanel. Metal aviator sunglasses, Jacques Marie Mage. Metal necklace, Jenny Bird. Vintage leather boots, What Goes Around Comes Around 

My Reading Room
My Reading Room

Cotton jacket; cotton shirt; embroidered cotton skirt; metal earrings; leather boots, Dior OPPOSITE: Silk fringe poncho; knit bra; metal earrings; leather boots, Dior

Makeup: Rachel Goodwin/ Streeters Hair: John Ruggiero/ The Wall Group Manicure: Christina Aviles/ Star Touch Agency Producer: Trever Swearingen/88 Phases Digital imaging: Luis Jaime/88 Phases Photographer’s assistants: Jaime Kang, Calvin Mendez, Danya Morrison Styling assistant: Kristen Layne Alvarez 
My Reading Room
Photographed by Yu Tsai.
Styled by Deborah Afshani