Whitney Port's Empowering Journey: Balancing Family, Fashion, and Self-Care

Whitney Port, known for her appearance on reality TV shows like "The Hills" and her own spinoff "The City," offers a refreshing voice of reason in a genre known for sensationalized drama. As a Teen Vogue intern on "The Hills," Port focused on providing thoughtful advice to her friend in the fashion closet, rather than getting caught up in the chaos. Even when she transitioned to her own show, "The City," in New York City, Port managed to navigate her early twenties on camera without succumbing to the typical pitfalls. "I was aware that I didn't want to embarrass myself because that's just not who I am," shares Port, now 38. "I had confidence in being true to myself, and that authenticity came across."

She still has a massive following, attracting hundreds of thousands of fans who tune in to her weekly podcast, "With Whit," and her YouTube channel. On these platforms, she discusses a wide range of topics, such as fashion, pop culture, and engages in conversations with her former colleagues and her husband, Tim Rosenman. Together, they share a 6-year-old son named Sonny. During the pandemic, their reaction videos to shows like The Hills and The City became popular, serving as comforting content for viewers.

Unlike her approach to reality TV, Port isn't afraid to share personal aspects of her life on her podcast. In 2021, she bravely opened up about experiencing her third miscarriage, and she also addressed the attention surrounding her weight earlier this year. Port believes that by being open and vulnerable, she can make others feel less alone. She shared these insights during an interview at Sunset Tower in L.A., where she discussed her journey of self-discovery with Us.

“When considering opinions, it is crucial to prioritize those from individuals who have a genuine understanding of your circumstances and who truly comprehend the essence of the situation. Nevertheless, the external environment can be quite challenging,” shares Port, according to Elizabeth Weinberg.

How are you feeling today?

I'm not feeling great at the moment, but I'm actively taking control and empowering myself, which will eventually have a positive impact. Currently, my focus is on self-care, avoiding overwhelming myself, and engaging in creative activities that serve as outlets for me.

What are your current projects?

I am currently engaged in various endeavors such as hosting my own podcast and YouTube channel where we provide entertaining reactions to reality shows. Additionally, I have partnered with Love, Whit for a collaboration with Rent the Runway, and we will be releasing a new fall collection this month. Furthermore, I am diligently working on curating a collection of vintage home goods and accessories, which will soon be available on my website. Recently, I have developed a newfound passion for interior design after renovating our office, and I am offering virtual styling services to my community. Sometimes, I ponder about how my career would have evolved had I not started in television, and I believe styling would have been a natural progression for me.

On your platforms, you have fearlessly addressed challenging subjects. During the summer, you bravely shared your experience with weight loss. What led you to express yourself on this matter?

After receiving numerous comments on a post I shared on [an Instagram], Timmy suggested that I address the situation. I am grateful for the genuine concerns expressed. However, the unnecessary remarks such as "Eat a burger" or "Maybe you should gain 20 pounds to get pregnant" are judgmental and uncalled for.

During New York Fashion Week, while alone in my hotel room, I noticed a post on Instagram that received numerous comments. Curiosity led me to investigate further, but to my dismay, it ignited a fiery anger within me. It has become utterly frustrating to constantly endure others passing judgment on my appearance without any knowledge or understanding. Fed up with this unjust scrutiny, I felt compelled to speak up and declare that I have finally reached my limit.

Has it prompted you to reevaluate your connection with food? It did - as individuals in my life, namely my close friends and sisters, expressed genuine concerns. Ignoring their worries would be negligent on my part. Previously, I never considered the significance of food, water, or even sleep. Now, I am compelled to give greater importance to nourishing myself adequately.

Have you ever experienced pressure to conform to a specific appearance while being in the spotlight?

Absolutely. When I first began filming The Hills, I had just completed my freshman year of college where I had gained a significant amount of weight. Seeing myself on screen compared to the other girls on the show made me realize how much bigger I appeared. This was the beginning of my struggle with food and body image. I was able to manage my weight for a while as I believed I was in a healthy place, but recently I have been dealing with some challenges.

What actions have you taken to improve your well-being?

I have consulted with a nutritionist and delved into identifying the root causes of my health concerns. It has come to my attention that my challenges are predominantly influenced by my surroundings. The passing of my father a decade ago and my five-year-long struggle with infertility have burdened me with immense sadness and grief. At times, I have denied the impact of these experiences, reluctant to confront them. Surprisingly, I have now come to recognize their detrimental effect on my physical well-being.

“I was excited to get dressed up and have fun, and not take life so seriously for a day,” Port says of her fashion shoot. Elizabeth Weinberg

Did discussing such a sensitive topic like pregnancy loss become difficult for you after initially finding it easy? It wasn't initially challenging but gradually became so as I continued to share my experiences. It wasn't because of any negative response I received, but rather because it became a constant reminder and a topic I had to constantly address. It started taking over my personal life and eventually bled into my professional life as a digital creator, where sharing personal experiences is part of the job. I felt like it became the primary topic of conversation and consumed every aspect of my life.

Timmy's support during this difficult period truly strengthened our bond. He empathetically reassured me, "We're in this together. It's not your sole burden, and it's not a fault of your body." Those simple words provided solace and made me feel understood, eradicating any sense of loneliness.

Do you still carry the pain from that experience?

Yes, it lingers. We are currently striving to determine the optimal course for ourselves, but surrendering is not an option. It remains a constant presence in my thoughts each day.

Earlier this year, you mentioned that you were contemplating surrogacy. We are currently exploring various options and experiencing numerous developments. However, I have chosen not to disclose everything as there have been a significant number of updates occurring in real-time. Moreover, I have yet to determine my exact sentiments towards these developments, hence I am not prepared to discuss the specifics of my plans.

You’d still like to expand your family.

I’d love to. I always wanted more than one. There’s just something in me that feels like we’re not complete yet.

Sonny has a strong desire for a sibling. This desire does not make me feel guilty, but rather he wants someone to be his companion and take care of. However, I don't think he fully comprehends the impact having a baby will have on his life! [Laughs] I don't want to lecture him about cherishing the present because in the future, when a baby arrives, things will change. Despite that, I am confident he will excel as an older sibling.

What do you appreciate about Sonny? His honesty makes me emotional. He shares my sensitivity and is incredibly kind. Even during something as simple as watching TV, he prefers my presence. This unique love, being needed in such a manner, truly delights me. Moreover, shaping this little individual into a fusion of [myself and Timmy] brings immense satisfaction.

“He’s more the disciplinarian and I’m the softie,” Port says of parenting Sonny with Rosenman. Courtesy of Whitney Port

What self-care activities do you engage in as a working mother?

I practice meditation and enjoy reading, sometimes opting for audiobooks during commutes. Despite initially hesitating, attending therapy always leaves me feeling rejuvenated.

You mentioned that depression is prevalent in your family. Was therapy always a regular aspect of your life?

No, it only began after my father's passing, and I have been attending therapy sporadically ever since then. I have never experienced depression or anxiety before. It was only after these events occurred that I felt the need to seek assistance.

What other modifications are you implementing?

I have always been inclined to experiment with a diverse range of things and assess their success. However, as I age, I realize that this approach can be excessively disorganized. Thus, I am striving to streamline my endeavors.

Would you ever return to reality TV?

I’m not so interested anymore. I don’t love being in front of the camera.

Are there any regrets you have from that period of time? I really wish I had taken better advantage of the countless opportunities that were available. I had the chance to spend time with influential individuals like Lisa Love and André Leon Talley, and looking back, I wish I had formed genuine connections with them. At that time, I had a huge ego and took many things for granted. However, I recognize that everything I get to do now is a result of those experiences. It's remarkable how I had the opportunity to be part of "The Hills" and "The City," but it's difficult for me to fully grasp how significant they were to people during that era.

Were you hesitant about joining The Hills?

I was raised watching shows like The Bachelor and The Amazing Race alongside my family. Consequently, my parents encouraged me to give it a try as it appeared enjoyable. [Laughs.] Moreover, I believed that since I was applying for an internship at Teen Vogue, the filming would mainly revolve around my work. At that time, I was in a relationship with someone who had no interest in being part of it, and that posed challenges. However, I made the decision to give it a shot, acknowledging that if I wanted to pursue a career in fashion, this opportunity was worth exploring.

Did you purposely choose to only display your composed persona?

Absolutely. I had to be intentional. Even during The City, and later during The Hills: New Beginnings [in 2019], if we went out, I made sure to limit myself to one drink so I wouldn't do anything embarrassing. It was tiring, but I knew I could handle it.

Have you ever declined requests from producers?

In all honesty, I did decline most of the time. I would say, "Look, I understand that we're making a show, but I prefer to express it in my own way. Let me find my own approach." It could sometimes lead to a disagreement, but I'm confident that producers wouldn't label me as the most difficult person. I'm absolutely certain of that. [Laughs.]

“I haven’t let any of that stuff change who I am,” Port says of her fame. Elizabeth Weinberg

Certainly! Did your castmates feel jealous when you got your own spinoff?

Absolutely. During the filming of New Beginnings, I could sense a bit of resentment towards me because it seemed like I didn't contribute much. However, I believe they didn't fully grasp the circumstances. In my opinion, a compelling TV show revolves around a relatable individual, depicting their life journey. I think viewers related to me because I was just an ordinary girl.

The City originated during our time in New York while filming for The Hills. Lauren and I were working on a project with Kelly Cutrone, and it was then that I had the chance to meet Jay [Lyon] in a natural way, and I genuinely developed a fondness for him. It was this connection that sparked the idea for Adam [DiVello], the creator, to consider relocating me to New York City.

Turns out, it became a real-life love story because your husband happened to be a producer on the show!

Interestingly, Timmy actually watched me on The Hills and later confessed to having a little crush on me. As the field producer, he was in charge of selecting our dining and club destinations. Consequently, we started talking about these topics and our connection grew stronger. He constantly expressed his readiness to quit his job because he didn't want to date a producer while they were documenting my life for the show. However, it wasn't until after the show ended, I returned to Los Angeles, and my then-boyfriend broke up with me, that I thought, "Maybe this is the right time for Timmy." Needless to say, I have never regretted that decision.

Listeners are enthralled by the podcast episodes featuring your date-night discussions. As we began recording as a duo, our audience expressed a strong desire to hear more from us. Recognizing the impact of sharing our authentic experiences on promoting social change, we wholeheartedly agreed to provide them with additional content.

What message do you have for your fans who want to see you happy and in good health?

I genuinely love them. If it wasn't for their support, I wouldn't still be pursuing this career. [Getting emotional.] Even in New York, people approached me and shared that they moved there because of The City. I was astonished, wondering how I had such an impact on them.

The significance of it makes all the difference. That's what motivates me and enables me to endure both the negatives and positives, as the positives far outweigh the negatives. Moreover, the genuine affection from others truly warms my heart.

To read more of our exclusive interview with Whitney Port, pick up the new issue of We, on newsstands now.

In this article

Whitney Port

The City

The Hills

The Hills: New Beginnings