11 Times Anna Kournikova Went Makeup-Free And Looked Flawless

From a rising tennis star to a devoted partner and mom, 42-year-old Anna Kournikova has evolved and changed a lot over the years. At the height of her tennis career, she won the Australian Open twice. However, it wasn't just her athletic skills that garnered her attention. Kournikova became well-known for her appearances on magazine covers, and her endorsements, too. When back issues meant she needed to retire from tennis, Anna took her career in a different direction, and appeared as a trainer on the show, "The Biggest Loser." Outside of her career, Kournikova's been a long-time partner of singer Enrique Iglesias with whom she shares three children. 

While she might not be in the spotlight as much as she used to, that doesn't mean she isn't living life to the fullest, or embracing the changes that come with it. In a 2008 interview with Sports Illustrated, she got candid about the subjects of beauty and aging, saying, "Here's one thing I don't get. Why are people afraid of getting older? You feel wiser. You feel more mature. You feel like you know yourself better. You would trade that for softer skin? Not me!" So it seems that Kournikova has swapped serving on the tennis court for serving stunning makeup-free looks, and is totally okay with it. 

Anna goes sans makeup in Italy

On a trip to Italy, Anna Kournikova rocked a gorgeous makeup-free look. In an Instagram post from May 2019, she can be seen smiling and flashing a peace sign. She paired her bare-skinned look with a simple high ponytail, a pair of sunglasses, and an understated but edgy outfit comprised of black jeans, a white tee, and a black moto jacket. The look as a whole is proof that you don't need makeup to create a vibe that's ultra-cool.

A bare-skinned and breezy boating adventure

In January 2019, the ex-tennis star can be seen sporting another casual no-makeup look. Sitting boatside with her hair pulled back in a high, wind-blown braided pony, she gives the camera a slight smile. At her feet are her two dogs, also lounging and looking relaxed in the setting sun.

Styling in shades

Wearing some gold-rimmed aviator shades, Anna Kournikova shares another glowing makeup-free look. In her Instagram post from December 2017, to which she added the hashtag "Miami winter," she pairs her sunglasses with a nylon jacket and some small stud earrings. Wisps of hair are flowing free from her ponytail, all coming together to make a boating look that's both polished and breezy.

Pre-workout glow

In September 2016, Anna Kournikova posted a glowing pre-workout selfie, to which she added some hashtags, including "positive vibes" and "workout time." In this photo, her hair is pulled back into a messy bun. Wearing some black headphones and a soft smile, she looks absolutely radiant and confident in her skin.

Fresh-faced weekend vibes

In another glowing selfie, Anna Kournikova lets her hair down in 2015 as she shows off her healthy skin and her beautiful no-makeup look. Accessorizing with some silver necklaces, her look is low-key but vibrant. With a hint of black on her eyelashes, it's possible she could be rocking a low-effort eye look, which will be super on-trend for spring 2024.

Bare skin while doing Pilates

From her 2014 post, it's clear that Anna Kournikova understands the benefits of Pilates. She looked beautiful while going without makeup again as she exercised, and cuddled with her big pup whom she hashtagged as her "best workout partner." In some pink and black workout gear and with her hair tied up in a messy bun, Kournikova looks like she's ready to get in a good workout, and have some fun while she's doing it, too.

Supporting the troops

Geared up in some trademark sunglasses along with a protective helmet, vest, and black coat, Anna Kournikova paired her long, slender braid with a makeup-free face while supporting the troops in Iraq in 2009. Her 2015 post reflects on the time overseas, hashtagging the experience as "life-changing." 

Doing yoga and glowing

In a post from May 2015, Anna Kournikova looks like she knows the pros of trying out yoga. In a post where she uses the hashtags "take care of yourself" and "inner peace," she can be seen in a pose called a dead bug, or happy baby. She looks relaxed, serene, and glowing without any makeup on. Her hair is tied up in a bun, and she sports some stud earrings along with her black workout outfit.

Makeup-free selfies in Minnie Mouse headphones

In an Instagram post from December 2014, Anna Kournikova dons some bold sunglasses, a pair of ultra-cute and nostalgic Minnie Mouse headphones, and a mysterious smile along with her bare-skinned look. A black top and a stylish silver chain bring the look together in a way that's both eye-catchingly cute and understated at once.

Living it up without makeup in the lake

Anna Kournikova doesn't just ditch the makeup when she's hanging out at home — she goes makeup-free to go swimming, too. Pictured again with her beloved pet, Kournikova can be seen having fun in the water in a September 2014 post. Along with glowing healthy skin, she's styled in a white swimsuit with a high pony as well as stud earrings and plenty of bracelets. It seems she wasn't worried about all the reasons you may want to leave jewelry at home for a beach day!

Clean-skinned and ready for bed

Cozied-up and clean-skinned Anna Kournikova posted a throwback pic of her and her puppy in September 2014. They make a perfect picture of cute comfiness with Kournikova in a cherry-print bathrobe. Her hair is tied back and her long bangs (that look a lot like the shadow bang trend) hang free, creating a look that's soft, relaxed, and naturally beautiful.