Cara Santana Is Complicated AF, and I Think You'll Really Like Her

“Everyone hates riding in a car with me because I only listen to CNN,” Cara Santana tells me, confirming that she’s a woman after my own heart. “I always wanted to be one of those cool girls who listens to the cool music. Really, I’m more of a Jake Tapper fan.” Standing there outside the H&M store on the corner of Fifth Avenue and 18th Street in her oversize gold earrings and chunky Maison Margiela sneakers, Santana—who lives between the glitz of the Hollywood Hills and grit of New York’s Lower East Side—is the very picture of one of the cool girls she claims not to be.

Although she’s 33 years old and engaged (I belatedly discovered her fiancé is actor Jesse Metcalfe), the actress, influencer, and beauty entrepreneur is one of those women who will undoubtedly be referred to as a “girl” for another decade, at least. I can’t help but like her a lot—and not just because she has a thing for Jake Tapper and also uses characters off Friends as a means to articulate personality types. It takes about three minutes to realize that Santana sits comfortably atop a mountain of contradictory personality traits, unworried that her unbridled enthusiasm for animal videos on Instagram somehow takes away from anything more serious she has to say. I like that in a woman.

While on the subject of things we care about to the point of obsession, Santana launches into an impassioned monologue covering civil rights, the state of our democracy, and issues facing minorities in general (“I’m not just talking about race; I’m talking about gender, sexual orientation—the list goes on and on”), before telling me she’s fanatical about a reality TV show called 90 Day Fiancé. (“I’ve seen every episode, every reunion, the follow-up shows…”) The trajectory is dizzying but refreshing.

In the spirit of H&M’s “For Every You” fall campaign, Santana and I had a lot more to talk about.


(Image credit: Patterned dress, faux-fur jacket, captain's cap, hoop earrings, sneakers, and shoulder bag all from H&M F/W 18)

Is getting dressed up fun or a pain in the ass?

I love getting dressed up, but it can be cumbersome. I think coming home from NYFW, it’ll be nice to chill in some athleisure.

How do you find the experience of having everyone be so interested in what you choose to wear—particularly when, as a woman, it’s something that seems to make or break your career? Is there any kind of male equivalent for this?

I think men are judged based on their appearance as well. I feel like we’re quick to categorize people. My fiancé is a great example of someone who, at one time, there was a certain opinion held about him, and through his career that has changed based on a myriad of things. So I see that it happens; maybe not to the degree that women face of judgment and observation, but I really don’t care. I just get dressed for me. Everyone’s got an opinion. You drive yourself crazy if you try to make everyone happy.

Do you have a uniform or do you experiment?

I totally experiment with my style. I allow my mood on any given day to dictate what I wear. Right now, I keep asking myself, Would Zoë Kravitz wear this? Would Diane Kruger wear this? Would Cate Blanchett? Julianne Moore? Which sounds crazy because they’re all incredibly different.

How do you find your look for all the different events you attend? Do you work with a stylist?

I work with a stylist for events and appearances; I think it’s great to have someone push you stylistically, and help you cultivate and curate your personal style. And I’ve been working with Maeve Reilly now for a little over two years. She’s actually a long-standing friend of mine, and she knows me really well, so it’s fun to let her play with an element of myself that I’m not necessarily keyed in to. I love it; I love experimenting with fashion and allowing your aesthetic to speak for you.

Do you feel like you get stereotyped?

People think I’m more style than substance. Maybe a little superficial, potentially uncool. Not very edgy. In reality, I think I’m a little more thoughtful than people would assume. Probably a little bit more edgy than they would think, with a little bit more depth than I think meets the eye. I think in Hollywood, certain things qualify people into different categories—the cool girl, the cheesy girl, the quirky girl, the elevated girl—and frankly, I think most of us are an amalgamation of all of them. I think I certainly am.


(Image credit: Wool-blend coat, paperbag pants, and sandals all from H&M F/W 18.)

Give us some insight into your inner monologue.

I’m full of questions. Am I doing enough? Am I doing this right? Am I doing too much? Am I a pushover? Am I too strong? Was I mean? Was I too nice? Should I have spoken my mind and been honest about how that made me feel? Did I say too much? Does this make me happy? Will this make me happy? I’m 33, so I feel as though I’m really trying to identify the next chapter of my life and make sure I’m the woman I aspire to be.

How do you want to go down in history?

As someone known for standing up for what they believed in—someone who was ambitious, smart, and true to her convictions.

In what ways do you consider yourself wonderfully contradictory?

I think we’re all full of dualities. I think I’m full of contradictions, to be totally honest. I’m strong at times and soft in others. I can be terribly insecure but appear wildly confident. I can be very, very serious and focused, and on the other hand be silly and naïve. I think that’s the beauty of being a woman—that you can be multifaceted.

In a three words, how would Jesse describe you?

Independent, sweet, sensitive.

How would your assistant describe you?

Demanding, specific, direct. I think my personality differs when it comes to business: I’m incredibly focused on getting the job done. I’m able to separate my emotions and also work from a very pragmatic place. I become more of a “feelings aren’t facts” type of person. As opposed to my friendships, where I’m much more overtly sensitive.

Your friends?

Type A. My good friend Stephanie [Shepard] always tells me that if I were in the cast of Friends, I would definitely be Monica.

How about your family?

Incredibly stubborn. I was always the type of child—and now adult—who had to touch a burning stove to know it was hot. They would say I’m outspoken. My mother always tells the story of dropping me off in the carpool line at school and me noticing the marquee said “Good will on earth and peace to all mankind.” I marched right up to the headmaster and said, “Hey, Mr. Whaler, don’t you think you should change that to ‘womankind’? Don’t you think ‘humankind’ is more inclusive?” I was in fifth grade.


(Image credit: Knit sweater, wide high ankle jeans, ankle boots, and bucket bag all from H&M F/W 18)

What did you want to be when you grew up?

I always wanted to be an actress. Ever since I was a little girl, I loved escapism, I loved creating, and I loved fantasy. I really love stepping outside of myself and into someone else’s shoes.

What’s the best advice you’ve ever been given?

My mom always said, “Your best quality in excess can be your biggest detriment.” And I think there’s a lot of truth to that.

Tell me about your recent story for Harper’s Bazaar.

As the immigration crisis was unfolding [at the Mexican border], I really started to feel helpless and uncomfortable with the limitations I was feeling as an individual. After some reflection, I felt like I offered a unique perspective, having grown up on the border of El Paso, Texas, and Ciudad Juarez, Mexico. So at 9 p.m. on a Wednesday night, I decided to book a trip back to my hometown.

It was the first time I had been home in 15 years. I made it my mission to reach out to everyone I know, from every element and perspective of the crisis, to really understand what was happening. I reached out to Chrissy Rutherford, a fashion editor at Harper’s Bazaar, and she connected me with Olivia Fleming, a features editor. I asked them for a platform to tell the story as I saw it unfolding.

What’s a really great quote?

“Take your criticism seriously, but not personally.” That’s Hillary Clinton.

What’s your take on how the world at large understands complicated women?

I think as of late, with the explosion of the #MeToo movement and having women’s rights at the forefront of popular culture, we’ve made incredible strides. I feel as though it would be naïve to think there wasn’t much more to do. Recognizing the work ahead of us is of paramount importance, but I’m certainly proud to be a part of a societal shift that’s looking to evolve and find a new way forward. And there’s no better time to be a woman.

What should women be talking about right now?

The upcoming midterm elections, and how that has a direct result and impact on our future rights and the rights of women to come after us. I feel like women should be talking about issues relating to this immigration crisis and how families are being torn apart, and how important it is for early development for a child and mother to be together. We should be talking about quality, equal pay… I don’t think there’s an issue we shouldn’t be talking about.


Natalie Cantell
Executive Director, Brand Studio

Natalie leads the style direction for the all content we create in partnership with our friends at various brands plus the legendary team of editors who work on those shoots and stories. She loves collaborating and storytelling, so it's a really fun role for her. It's also the first full-time job she's ever had⁠! She started out in her career as a very mediocre model who agreed to her first styling job to impress a photographer she had a crush on, which led her down a happy path of contributing to Vogue Australia and working as a stylist, fashion writer, and creative director for all sorts of brands and titles. She has a bachelor of communications, but most of her career opportunities came up thanks to some fleeting and accidental street style moments. She's been at Who What Wear for three and a half years and still loves to work as a freelance consultant with brands and designers to shoot their campaigns in NYC. She's originally from New Zealand, and Bondi Beach is her second home, but like just about every other 20-something, she fell in love with New York at some point. She lives in Williamsburg with her fiancé and their weird little dog, Ruby. If you ever need reccies for feel-good fashion, legit coffee spots, politics podcasts, or non-intimidating yoga studios, she's very much your girl.