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Whitney Port on Family, Fashion and Finding Her Way: ‘I’m Taking Care of Myself’ (Exclusive)

In reality TV, a genre of table-flipping and boyfriend-stealing, a voice of reason can be a welcome reprieve. Whitney Port would know. Upon making her 2006 debut on The Hills as a Teen Vogue intern, the L.A. native steered clear of major drama in favor of offering thoughtful advice to her friend in the fashion closet, Lauren Conrad.

Even when Port stepped into the spotlight with her own spinoff, The City — which followed her to NYC, where she’d landed a glitzy new job and an on-camera boyfriend — she managed to avoid the common pitfalls of playing out your early 20s on TV. “I knew I wasn’t going to make a fool of myself because I just don’t do that,” Port, 38, says. “That’s not who I am. So I felt OK going into it knowing that I could be myself and that would shine through.”

It’s the reason she still has a massive following. Between her weekly podcast, “With Whit,” and her eponymous YouTube channel, hundreds of thousands of fans tune in to hear her musings on everything from fashion to pop culture and conversations with old costars and her husband, Tim Rosenman, with whom she shares 6-year-old son Sonny. The pair’s reaction videos to The Hills and The City, which featured them gasping, cringing and laughing on their couch while rewatching episodes, became ultimate comfort viewing during the pandemic.

But unlike her approach to reality TV, Port isn’t afraid to get personal on her podcast. In 2021, she revealed the heartbreaking news that she’d suffered her third miscarriage, and earlier this year, the fashion designer and influencer addressed headlines about her weight. “I thought, ‘This is what my community is about,’” Port says. “I want to be vulnerable and share my truth because if I can help even just one person not feel so alone, then it’s worth it.” Port sat down with Us at Sunset Tower in L.A. to share more about her journey of self-discovery.

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“I think it’s important to only place value on the opinions of people who really know you and what’s going on. But it can be a tough world out there,” says Port. Elizabeth Weinberg

How are you feeling today?
I don’t feel great yet, but I’m taking charge, and that empowerment will eventually help with that. Right now, I’m in this zone of taking care of myself, not spreading myself too thin, and just doing things that are creative outlets for me.

What projects are you working on?
I have my podcast and YouTube channel, where we react to fun reality shows, my Love, Whit x Rent the Runway collaboration, with a fall collection coming out this month, and I’m working on a vintage home goods and accessories curation, which will launch on my website soon. We recently renovated our office, so interior design has been a new passion of mine, and I’m doing virtual styling with my community. I always think that if I didn’t start my career on TV, I would’ve progressed into styling.

You haven’t been afraid to discuss difficult topics on your platforms. This summer, you opened up about your weight loss. What prompted you to speak out?
I started seeing all the comments on [an Instagram] post I had done, and Timmy was like, “Maybe this is something you want to clear up.” The concerns that were real, I appreciate. It’s the judginess of “Eat a burger,” or “Maybe if you gain 20 pounds, you’d actually get pregnant,” those things that are so unnecessary.

Whitney Port and Tim Rosenman Relationship Timeline

Related: Whitney Port and Tim Rosenman’s Relationship Timeline

You also addressed that on Instagram, asking people to stop commenting on your body.
I was in my hotel room by myself [during New York Fashion Week], and I saw one particular post had a lot of comments. So I’m like, let’s see what’s happening here, and honestly, it just made my blood boil. I’m so sick of having other people have an opinion about how I look when they know nothing. So I was like, “I have to say something. I’ve had enough.”

Did it push you to examine your relationship with food?
[Yes] because there were people in my life who were actually expressing concerns. I can’t turn a blind eye to my best friend or sisters. I wasn’t thinking about food as a priority or water as a priority or sleep as a priority. I need to take nourishing myself more seriously.

Being in the spotlight, did you ever feel pressure to look a certain way?
Definitely. When I started filming The Hills, I was coming off of my freshman year of college, where I’d gained a ton of weight. And then I saw myself on screen and was like, “Oh my God, I’m so much bigger than all the other girls on the show.” I think it was the first thing that started affecting my relationship with food. [Later] I was always able to maintain [my weight] because I felt like I was in a healthy spot. It’s just this past year stuff caught up with me.

What steps have you been taking to get to a healthier place?
I’ve [been meeting] with a nutritionist, and now I’m digging into what my actual issues are. What I’ve realized is that they’re entirely environmental. I lost my dad 10 years ago. I’ve been on an infertility journey of five years, and there was just so much sadness and loss. Sometimes, you can be in denial about that stuff because you don’t want to have to take a look at it. I didn’t even realize it was affecting my physical health in that way.

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“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

You’ve shared your experiences with pregnancy loss. Was it hard to discuss such a sensitive topic?
It wasn’t at first, and then the more I put it out there, it was. Not because I was getting any negative response but it became something that I had to talk about and be reminded of all the time. It was already taking over my life, and then it was taking over my professional life. As a digital creator, you’re in this world of showing your personal life as part of your business. So I felt like that was becoming the conversation, and it was all-encompassing.

How did Timmy support you during such a challenging time?
It really did bring us closer together. Timmy [would say], “This is us dealing with this. This is not you dealing with this, and this is nothing that your body did wrong.” I feel like sometimes that’s all the partner needs to say for the woman to not feel alone.

Is the pain of that experience still with you?
Yeah, it doesn’t just go away. And we’re trying to figure out the best plan for us, but I don’t want to give up. It’s still something that’s on my mind every single day.

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Related: Rowan! Sonny! Get to Know 'The Hills’ Next Generation

You told Us earlier this year you were considering surrogacy.
We’re exploring everything, and we’ve had a lot of that stuff happen that I’ve chosen not to share because at a certain point, there’s just so many updates, and it’s happening in real time, and I’m not even sure how I feel about it. So I’m not ready to talk about the details 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.

Does Sonny want a sibling?
So badly. Never in a way that makes me feel bad, but he wants a buddy or someone to look after. I don’t think he realizes what that will mean for him once the baby comes! [Laughs]. I don’t want to be like, “Hey, appreciate this now, because in a year, or two years, or whenever it happens…” But he’s going to be the best big brother.

What are some of your favorite things about Sonny?
Honesty, I could cry. He is so sensitive like me, and he’s so sweet. Even if he’s just watching TV, he wants me near him. It’s a different kind of love; being needed in that way feels so good to me. And molding this little human into someone, like a combination of [me and Timmy], is so rewarding.

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

As a working mom, what kinds of things do you do for self-care?
I meditate. I read, or I’m more like a listening-to-Audible-in-the-car type of person. My therapy, even though I’ll dread it up until the second I get there, afterward I always feel better.

You’ve shared that depression runs in your family. Has therapy always been a part of your life?
No. I started right after my dad passed away, and I’ve gone off and on since then. I never was a depressed or anxious person. It wasn’t until this stuff happened to me that I needed to reach out and get some help.

What other changes are you making?
I’ve always been the type of person who will try a million different things and see what sticks. As I’m getting older, I’m finding that that’s a little bit too chaotic for me, and I’m trying to simplify things.

Would you ever return to reality TV?
I’m not so interested anymore. I don’t love being in front of the camera.

The Hills Original Cast Where Are They Now

Related: 'The Hills' Original Cast: Where Are They Now?

Do you have any regrets from that period of time?
I wish I’d taken more advantage of the opportunities that were there. I [was] with Lisa Love or André Leon Talley and all these amazing people who I wish I’d forged real personal connections with. I thought I was hot s–t, you know? I took so many things for granted. [But] I know everything I get to do now is because of it. I think it’s so cool that I was able to do [The Hills and The City], but it’s hard for me to see from the outside how big it was to people at the time.

Did you have any reservations about joining The Hills?
I grew up watching shows like The Bachelor and The Amazing Race with my family. So my parents were like, “Go for it! That seems fun!” [Laughs.] And I felt because I was interviewing for this internship at Teen Vogue, they’d just be filming me at a job. I was dating someone at the time who wanted nothing to do with it, and that was hard. But I was like, “Listen, if I want to be in fashion, let’s try this out.”

Did you consciously decide only to show your put-together side?
Oh, definitely. I had to be calculated. I still was even for The City, and when we did The Hills: New Beginnings [in 2019], if we were going out, I was cognizant of having one drink so I didn’t do anything to embarrass myself. It was also exhausting, but I knew I could manage it.

Did you ever say no to things producers wanted you to do?
Honestly, most times. I’d say, “Listen, I know we’re trying to film a show, so I’m not going to say it that way. Let me get there on my own.” It could be a battle, but I’m sure producers wouldn’t say I was the most difficult one. I’m just sure of it. [Laughs.]

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

Definitely; you got your own spinoff! Was there any jealousy from your castmates?
For sure. When we were filming New Beginnings, I could sense a little resentment toward me because it was like, “She never really gave anything.” But I think they weren’t understanding the situation. What makes a good TV show, I think, is getting someone who people can identify with and watching how they navigate life. And I think people identified with me because I was a normal girl.

How did The City come about?
We were in New York filming for The Hills. Lauren and I were doing something with Kelly Cutrone, and I met [ex] Jay [Lyon] organically, and I really liked him. I think that’s what prompted [creator] Adam [DiVello] to have the idea to move me to NYC.

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Related: 23 Most Memorable Moments From ‘The Hills’

And it turned out to be a real-life love story because your husband was a producer on the show!
Timmy actually watched me on The Hills and [later] said he’d had a little crush on me. He was the field producer, so he was responsible for finding where we’d go out to eat or a club. So I’d talk to him about that stuff, and it developed into us BBM-ing and having this emotional connection. He kept saying he’d quit [because] I couldn’t be dating a producer while they were trying to make a show about my life. It wasn’t until it was over, and I moved back to L.A., and my then-boyfriend dumped me that I was like, “OK, maybe this is the time for Timmy.” Obviously I never looked back.

People love the date-night episodes the two of you do on your podcast.
We started recording together and then [listeners] were like, “We want to hear more of you two.” He really feels like sharing our truth is actually what makes a difference in making social change, so we were like, “OK, let’s give them more.”

You connect with so many fans across your platforms. What’s your message to everyone who wants to see you happy and healthy?
That I actually love them. I wouldn’t still be doing this if it weren’t for them. [Tearing up.] Even when I was in New York, people came up to me and said they moved to New York because of The City. I was like, “Oh my God, how did I have that effect?”

It’s a meaningful thing.
It is. So, that’s what keeps me going, and why I can take the bad with the good, because it’s so much more good than it is bad. And I do feel like people actually love me, which feels really nice.

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

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