On Monday night, celebrity stylist Sam Woolf was awarded Style Moment of the Year at the Fashion Awards in London, and you can trust he’s worked insanely hard to get here. Having worked with the likes of Doechii, Jennie, Jhené Aiko, Teyana Taylor, and more throughout the past year on looks you definitely will have seen (and saved to your mood boards), Sam Woolf’s styling is consistently viral.
We asked Sam what advice he has for emerging stylists, his favourite looks in 2025, and whether his work’s virality is an end goal or an afterthought. Keep reading to find out what he had to say.
Congratulations on winning the Pandora Style Moment of the Year Award! How does it feel to have your work recognised at The Fashion Awards?
“Thank you so much! I genuinely am so grateful to be honored by such important global brands that support emerging talent and creatives like Pandora and the British Fashion Council. It’s really so monumental and surreal, but I couldn’t be more excited.”
You’ve styled Doechii a lot in 2025. How’s it been working with her?
“I’m so lucky to work with someone as creative and passionate as Doechii. We are such a collaborative team, because we both have so many ideas that we bounce off each other and get to bring to life.”
Do you think you were styling Doechii with the awareness that your looks would become so culturally impactful?
“Never, and that’s not what we work towards. It’s more important to us to build a look that continues the story we are trying to tell than to build a look that will go viral because virality is fickle. Being authentic to who Doechii is as a person and what she is passionate about is our goal, and leads to those culturally impactful moments.”
The moment before the Met Gala, where you helped Doechii recreate an iconic André Leon Talley moment, was historic. Was it challenging to style that look to match the original?
“The theme of the Met Gala was so inline with who Andre was as a Black dandy, so he became an inspiration for us to reference throughout the weekend. The team at Louis Vuitton was so helpful in providing us with pieces that were Louis Vuitton, and I went vintage sourcing to find the clothing items that looked similar to what he was wearing even down to the faded fabric of the red sweater.”
What’s been your favourite look you styled in 2025?
“Doechii’s custom Thom Browne look for the 2025 Grammys.”
What was the most challenging look you created this year?
“I think Glastonbury was a challenge as it was a live performance with super fast quick changes that we had to do in 30-45 seconds. So, I had to style in a way that was logistically going to work in order to make the quick changes seem less.”
You don’t only work with Doechii — you’ve also styled Jennie, Jhené Aiko, Teyana Taylor, and more. What would you say makes someone enjoyable or easy to style?
“For me, the finished product and watching my clients feel comfortable and confident make it all worth it. I’m fortunate that all the ladies you mentioned are so open in terms of style and experimenting with fashion, so it’s always fun pushing the boundaries with them.”
Can you share a look you styled in 2025 that you knew would be a major moment?
“We truly never know how successful or viral a moment will be, we just do us. I think a super fun major moment was Doechii opening the Dsquared2 show in Milan, and it was the beginning of an iconic week.”
Can you tell us about a look you styled where the reaction surprised you?
“I absolutely loved Doechii’s Willy Chavarria look on Tiny Desk, but I was honestly so surprised by how many people loved it, as it’s a risk putting a woman in such a masculine look. Not everyone understands that.”
What’s a brand or designer you will always return to?
“There are so many. We obviously have been super obsessed with Thom Browne, Miu Miu, Willy, Dsquared2, and Schiaparelli.”
What’s a look that you didn’t personally style but loved this year?
“Jenna Ortega and Enrique Melendez really killed it on the “Wednesday” press tour. So many of their moments were standouts for me.”
What piece of advice would you give to emerging creatives wanting to pursue a similar path?
“Keep going. Everyone says it, but success doesn’t happen overnight. It’s taken me 10 years to get here, and I couldn’t have made it without the lessons learned along the way.”
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