The Fashion Fairy Godmother Caroline Vazzana Was Always Destined To Be

Caroline Vazzana has built her career around helping others understand that there are no ‘wrong’ answers when it comes to self-expression, and that the pursuit of a fashionable life can be an expression of joy.

When Pinterest decided to turn its member’s digital vision boards into an episodic, documentary-like chronicle of making goals into reality, it felt logical for Vazzana to expand on her perspective with new work that would depend heavily on her ability to coach and explain.

“The last time I spoke to you,” Caroline Vazzana said when we met up on Zoom, “I don’t think I was allowed to talk about any of it yet. And I remember being like, I want to tell her about it so badly. But long story short, months ago, I got this email from Pinterest. I’ve worked with Pinterest for years in much smaller capacities. Essentially, they were casting for this show, and they wanted me to be the host for two fashion episodes. Now, I have never hosted TV before, this was very new to me. But I talked it over with my team and they were like, this would be the perfect next step for you. You know, I’m already in my closet all the time teaching people, why not take what I’m already doing, and put it out in the world.”

I asked how similar the filming was to the work she has been doing online for the better part of a decade. Obviously a produced series is a specialized thing, it has its own processes, but I could see how the work Vazzana would be likely to at least be tangentially related in helpful ways. Maybe she hadn’t done this exact type of work before, but she already knows her audience intimately, and more importantly, she loves that audience. She is inspired and invigorated by having the opportunity to share with the people who follow her work, to gift them with her adoration and enthusiasm about the fashion she loves and is extremely knowledgeable about.

“It’s interesting,” Vazzana told me, “I’ll produce a video for social media and it’ll just be me, maybe one other person, and my phone. For this, I walked in and there was a whole crew and it’s so interesting to see how it all comes together. They told me that often people who are social media personalities are the best hosts because we’re used to seeing ourselves on camera or speaking to a camera. Even though it’s alone, I’m used to filming in my closet, and it’s still just filming, I’m still talking to a camera. It was really beautiful to get to take years and years of filming a Get Ready With Me, or a What’s On My Desk Wednesday, and have that be practice now for a TV show. And B-17 Entertainment was amazing to work with, they made everything seamless.”

Fashion Is Beyond Clothing

The title of the show pretty well explains what it is, but there are a lot of ways that a series like this could have gone, a lot of tones to choose from, a lot of factors that depended greatly on the lens through which these transformation stories would be told.

“We filmed my episodes of Bring My Pinterest to Life over a week in LA back in November,” Vazzana explained. “It’s sort of like What Not To Wear, but way nicer, we don’t rip anyone apart; it’s like I’m your best friend or your big sis. I think of myself as a fashion fairy godmother, coming in and trying to help you become the fashion person you want to be. We go through their Pinterest boards, they create essentially mood boards of how they want to dress, or who they see themselves as. And that’s the beauty of fashion, that’s what I try to talk about in the show, this is beyond clothing. It’s like a lifestyle and a confidence change. I personally see fashion as so much more than just throwing something on.”

How did Caroline Vazzana, who has made a massive impact on the perception of maximalist fashion in the 21st century, choose what she would wear to host her episodes? She has so many choices and could have taken this in any one of a dozen (or more) equally stylish directions. How did she even know where to start planning that aspect?

“I could walk onto the show in like a neon tulle ball gown and be good to go,” she laughed to me with a grin. “Action. But I felt like we needed to make maximalist and wearability meet for something that could relate well on TV, and they needed to introduce me to someone who’s never met me before, who doesn’t know who I am at all. I wore some fun Christopher John Rogers pieces. And then I mixed in some things that were super cool from Anthropologie. I brought in some stuff from Francis Valentin, and some Alice + Olivia sparkles. I wore this amazing gold sequined suit in my interviews, which was really, really fun. It was fun to play around and pull from my own closet and put together things that I’ve had forever. But, how can we mix them in new and exciting ways? And then to see myself on a TV screen, I’m like, ‘this is very odd, this is crazy.’ I’m so used to seeing myself on a phone, it’s so small and it’s been really surreal.”

Step In To Who You Could Be

And what were her episodes like? What did she try to focus on when helping people she’d never met before curate their wardrobes to better articulate their internal experience, to share with the world the look a person feels is their own. That’s not exactly a simple or small goal, though the lady achieves it with a natural effervescence.

“The two people that I worked with had completely different stories,” Vazzana explained, “completely different backgrounds. But the ultimate center of it all was wanting a change, wanting to step into who they felt like they could be. We say fashion is like armor. It’s like a personality change, right? One day I can be girly and feminine and the next day I can be punk rock. And so I feel like for them, it’s like changing their wardrobe to meet the person they want to become. Clothing is how you can present yourself to the world. And even if you’re not emotionally there yet, like 100% I am a boss, clothing can help you pretend I am for the time being, until you are there. It was such an incredible experience. I worked very closely with the Pinterest team and with the other talent on the show to really understand what they were hoping to achieve. I feel like it was a nice modern day take on a makeover show.”

The other four episodes of Bring My Pinterest to Life’s first season feature the DIY designer, Drew Michael Scott and interior design guru Tay BeepBoop, and when the series debuted this spring there was a press screening in New York City, where Vazzana is located. But more special to her was being able to show the finished episodes with her family.

“When it came out I did a viewing with my parents,” she told me. “They came over and so did my sister and brother and there’s a billboard now in Times Square. I brought my parents to see it and they were so proud. It’s been a really cool project because so much of what I do is just on my phone. And this is like stepping out of my comfort zone and into a new medium.”

A Fashion Fairy Godmother

I would have felt as though I’d missed an opportunity if I didn’t made time in our conversation ask Vazzana about the current state of fashion, what was inspiring optimism in her worldview as spring approached summer in 2026. So I asked her which designers, maybe up-and-coming, maybe around for a while but still lesser known, were connecting with her as an aesthete right now. How she chose what work to wear, what designers to feature when curating another about-to-go-viral Get Dressed With Me fashion post.

“Tabbe Designs made my inflatable dress,” Vazzana said immediately. “I think she is so slept on. Obviously these are not pieces you can wear every day because they’re so kitschy and niche but who doesn’t want a little inflatable top to go with their jeans? That was definitely such a moment. She’s a new emerging brand, just starting out and I love her. There’s also this designer Emma Gage, MEKLE is the brand and she is such an incredible talent, so creative. She does incredible bead work, she made this martini dress with little beaded olives. I love her so much.”

“I just went to Bach Mai’s show during fashion week,” Vazzana continued. “He’s so creative and no one does draping or just appreciates a woman’s body like he does. I am tall and pants for me are the worst, but for the last few fashion weeks he’s very kindly dressed me for his show. When I go to his studio, I’ll try on a bunch of things and his pants always fit and it’s a beautiful thing. He’s just a great human being and the same with Emma, I don’t know the designer of Tabbe personally but we’ve talked virtually, just gushing over each other and I think they deserve all the love.”

Don’t Be Afraid of Nonexistent Judgement

Caroline Vazzana is really good at making friends, at building community, and it seems likely that this is partly the result of her attitude. She does not want to talk anyone down, she never has a harsh word to spread; she very much lives the life she has put online. Vazzana is kind, she gets a lot of joy out of her work, and if she can help you to make your life better by embracing fashion or style, she will double down on her efforts. This is very much a woman who sees how a rising tide can lift more than just her own ship. Thinking about this, I asked her about the cartoon-ish pair of jeans she famously wore out in NYC earlier this year, about their designer and the response she received online and off.

“The designer of the box jeans is KSENIASCHNAIDER,” Vazzana told me, “and I haven’t met her personally, but I’ll mention her philosophy because we got interviewed by The New York Post. They reached out to me after my video went insanely viral, and I said to them, you need to go interview the designer, this is not my story! I had a long conversation with them about my thoughts behind the jeans and why I wore them, but then I said the person you should really be talking to is the person that made them, it’s her story, it’s her baby. And it’s funny, she made them because they looked like Minecraft and she wanted to see if she could do it. Now they’ve gone insanely viral, and she messaged me the other day to say she was making square red sweatpants, and could she send me a pair? I’m going to style them with sparkly Margiela pumps and run around the city. It’s so much fun to have built this relationship with someone I haven’t ever met. I reached out to her randomly and now we’re collaborating. I’ve built connections with beautiful people who are excited when I wear their designs and then we collaborate and get to work together.”

Knowing intimately how many more such stories existed, I asked if she would tell me another, an example of her relationship building through fashion. After my own meetings with Vazzana, after watching and experiencing the ways she interacts with people online and off, I very much wanted her help in articulating the importance of friendship that grows out of mutual admiration.

“I was Cher for Halloween,” Vazzana said, “and Emma from Melk made a polka dot dress for me. I told her I needed a dress to be Cher, and she has a studio in Brooklyn, she’s like ‘come by like let’s do it!’ She admires what I do, and I admire what she does, it’s this beautiful thing. I feel like there’s this new era of young designers coming through in New York specifically and I feel really excited that I get to almost help usher them in, in a way.”

“Ksenia showed in London Fashion Week this season and next season I’m coming, because I want to wear the box jeans and I want to sit at her show. If Bach or Emma or the designer behind Tabbe Designs wants to reach out to me and collaborate, I’m very open to that. Because I know what it’s like when you’re starting out, trying to get your name out there and build a brand. I have this platform that I’ve built out of my love for fashion. My whole brand is fun, just having fun jumping around the city. Because life is too short, so let’s not be too serious. So, if I can help uplift in any way, I want to be in an inflatable dress.”

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