Whitney Port Complemented a Stranger—and It Landed Her at the Victoria’s Secret Fashion Show

Whitney Port has always had a way of making the extraordinary feel relatable. On With Whit, she recalls how she got to the Victoria’s Secret Fashion Show, proving sometimes, saying one small thing can change the entire vibe of your week.

It all started in an elevator at her New York hotel. Port spotted a woman whose outfit was too good not to mention—a chic Schiaparelli jacket, Miu Miu shoes, and a Birkin bag that practically belonged in a museum. Instead of keeping the admiration to herself, she leaned in with kindness. That quick compliment revealed a surprise connection and, within 24 hours, landed her an invitation to the most coveted fashion show in town.

When kindness pays off in Victoria’s Secret Fashion Show couture

“I am obsessed with your jacket. That is so cute,” Port recalls telling the woman in the elevator. As it turned out, that woman was Brooke, a close friend of Port’s best friend Joe. Within minutes, they were reconnecting, and by the next day, Brooke had extended an invitation to the Victoria’s Secret Fashion Show. “She was like, would you want to go? I’m like, yeah, I guess so,” Port shares with a laugh.

That openness—choosing to compliment a stranger—snowballed into one of the most coveted fashion invites in the world. It’s a reminder that energy really does come back around, even when it starts as something as simple as kind words.

Styling stress, solved

The invite sparked the “what to wear” dilemma. Luckily, Port had her go-to stylist, Lizzy, in her corner. Lizzy introduced her to Pickle, an app that lets you rent clothes from other people’s closets. Through it, Port scored a sleek, jersey long-sleeve dress by designer ARAKII, sourced from influencer Hannah Schönberg’s wardrobe. “It was so comfortable. It was a long-sleeve, spandexy jersey—didn’t have to wear a bra. I was so comfortable,” Port says.

Even though Victoria’s Secret offered vintage slip dresses as options, she chose the one that made her feel best. “The team was so nice. They were like, just feel comfortable, wear what you want,” she explains. That decision highlights something so many of us forget when faced with a big event: the best look is the one you feel at ease in.

Behind the red carpet glam

Like many women juggling work and life, Port admitted she almost skipped the full glam process. “Lately, I’ve just been not looking forward to getting hair and makeup done,” she says. But for the Victoria’s Secret Fashion Show, she went for it—with glam squad pros Jamie (makeup) and Isaac Davidson (hair) making sure she was red-carpet ready.

Still, it wasn’t seamless. Mid-prep, Port felt a wave of vertigo, likely because she hadn’t eaten enough during her busy day. Her quick fix? “I ordered a slice of pepperoni pizza and had a ginger ale. That brought me back to life,” she shares. Later, she doubled down with room service—grilled cheese, salad, and chocolate cake. The moment was funny, but also a gentle reminder that nourishment is non-negotiable, even when chasing the fashion high.

Mom guilt on the runway

As glamorous as the night was, Port admitted that real life tugged at her even as she walked the carpet. While she posed for cameras, an email pinged from her son Sunny’s school about an incident (thankfully not involving him). “It just made me feel anxious. Like, are my priorities straight?” she says.

That balance between career opportunities and family is something Port is constantly navigating. She framed it honestly, acknowledging that guilt is natural but also fleeting. “We leave space for it, we feel it, and then we let it pass,” she says.

From styling wins to credit card fraud headaches (yes, that happened the same week), Port was candid about how messy success can look. Still, she circled back to gratitude. “I am always saying to myself, wow, this is my life. I am so lucky. I am doing what I have always dreamt of doing,” she says.

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