From Shooting Vogue to Starting the IT Girl Movement With Olivia Bossert
Dear Creator,
What would you do if you’ve already achieved the dream you’ve been chasing since you were in your teens and then realize you have nothing planned for what’s next?
That’s what I talked to Olivia about in this conversation. We talked about the courage to shift paths, shoot for Vogue and then try to figure out those next steps.
Olivia is a brand photographer and artist on a mission to help women step into their It Girl era and become the It Girls of their industry.
With over 15 years of fashion photography experience, she blends creative direction and high-end editorial flair to craft personal brand shoots that feel elevated, expressive, and completely unforgettable.
When you listen to this episode of Dear Creator, you’ll hear our conversation about exploring the messy middle, uncomfortable space between who you were and who you’re becoming.
We remind you that transformation isn’t a personal betrayal — it’s part of your entire evolution which in some cases… surprise you!
Here are the key insights from this episode:
Daily Rituals & Creative Practices
To kick off our conversation, I was really interested in hearing about Olivia’s daily rituals or creative practices that help her have a really fucking good day. She explains how she spends 2 hours daily walking her dog, Milo in the UK countryside, rain or shine — which is a practice she’s maintained for years. It serves her and her dog.
She also creates something — whether its a drawing, painting, or writing in her journal. Anything counts and it helps her feel really good.
Identity Through Fashion
Olivia puts on a different character each morning based on how she wants to feel. We also talk about how adopting more masculine energy sometimes through her outfits helps her feel more sure of herself.
Her signature item is a scarf. It’s the go-to accessory that makes the outfit complete. And her love of fashion existed first and photography became the gateway into the fashion world — which she wanted to be a part of.
Olivia’s Photography Journey
Olivia’s uncle was a photography and told her at a young age that she took “very good photos, very naturally” after a trip to India — the first affirmation that she had a skill she didn’t know about.
She then taught herself photography basics before university with her dad’s Nikon (which she still has!!)
After graduation, she thought she’d do weddings since there was no fashion industry near her. After the first wedding, she instantly knew it wasn’t for her but still had 8 more booked.
She knew something had to change so she started pitching brands directly and had them send her clothes to shoot. And on the side of that she ran a separate business teaching photographers how to pitch to brands and get editorial work.
(Watch this conversation on YouTube)
Achieving the Dream to Work With Vogue
For years and years, the ultimate goal was “one day I’ll shoot for Vogue”. Then one day she woke up and it became a reality. Though this wasn’t her first attempt to work with Vogue…
She had pitched to Vogue many times before but the energy was just different when she made it an absolute goal versus a hopeful inquiry.
In the episode, she explained how when she looks back, she wasn’t ready until the moment landed. Olivia believes she needed the growth curve and building more production skills with confidence.
Vogue credit felt like the ultimate validation. Even with the decisive energy, she was still surprised when it happened because she’d be trying to get her moment with Vogue for so long.
Reflecting on the experience we talked about the idea of being “legit” and how it used to mean shooting for Vogue. But now, she believes:
For brand photographers: Can your images help them sell what they’re selling?
For art or passion-based photographers: It doesn’t need to do anything or be useful to anyone—self-expression is enough.
For wedding/consumer photographers: Are you making someone happy and feel good? Are you having fun?
The Pivot & What Came After
After shooting for Vogue, there was this little unsettling feeling on what to do next. There was a time that Olivia did portrait shoots for her mastermind coach and then another member, purely as favors and she didn’t think much of it.
What she realized was she’d been doing portraiture in fashion all along, especially working with celebrities and public figures who weren’t models — making uncomfortable people look and feel comfortable (that’s already her expertise).
When her mastermind peers shared the photos online, the response was unlike anything they’d gotten from previous shoots. There became a time where she did a similar shoot, with incredible results, and she finally reflected and was like “What am I doing? I’m really good at this”.
The realization finally settled in and shooting in this way was easy, results were insane, everyone loved it and she naturally got along with everyone she worked with because they were people she probably would hang out with anyways.
After this realization, she decided to go ALL in. She posted on Instagram that was completely out of the blue for her fashion photography followers and changed her content strategy.
Leading the IT Girl Movement
When Olivia worked with a messaging coach, during her pivot, the coach recommended using the “IT girl” as Olivia’s movement and to create a world around. Olivia was hesitant because she struggled with her own baggage around the term.
She associated the “IT Girl” with celebrities, arrogance, being the cool girl or popular girl at school — things she didn’t feel.
So she broke down in a journaling session, why she was struggling with the term. What she realized was that she needed to write her own definition.
When she talks about IT Girls, she means kind, self-assured, empathetic, going after your own dreams, has big goals and vision and pursues them just because she wants to.
She even had a viral moment on Threads and Instagram when she started talking about it. People said she completely changed their perspective.
Now when she works with clients and they call themselves “IT Girls”, Olivia is lit up!
Lessons & Advice From Olivia
Ask yourself — if you were the coolest girl you knew and didn’t worry about what anyone thought, how would you be living or show up? What would you be doing? Then actually do it.
You’ve only got one life. It’s short. It goes fast. You better have fun while you’re living it.
What you learn in one field often translates perfectly to another. Olivia’s fashion photography skills became the exact thing that makes her brand photography incredible.
When something stops feeling exciting, pay attention—that discomfort is information, not something to ignore.
In 2026, Olivia is focusing on embracing her multiple creative identities. She hired an art coach to help her launch her first art collection and fully claim being an artist who makes money from art.
We hope you enjoyed this episode and make sure to go find Olivia to follow her art ventures, IT Girl movement or book a portrait session.
Connect with Olivia
Website: www.oliviabossert.com
Instagram: www.instagram.com/oliviabossert
Archetype Freebie: https://oliviabossert.myflodesk.com/archetypes
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