Born and raised in Manila, Tiffany Rossdale has called Tokyo home for over 25 years. A true renaissance woman, she has lived many lives, first as a celebrated figure in Japan’s vibrant VIP nightlife scene, and now as a transformational lifestyle coach and LGBTQ+ wellness advocate. After arriving in Tokyo in the late 1990s, Tiffany quickly became one of the city’s most recognizable socialites, curating dazzling fashion events and luxury parties under her brand Tokyo Fashionista for five-star hotels, top fashion labels, and mega-clubs. She has worked alongside international talents including Kat DeLuna, Vita Chambers, and Lavelle Smith Jr., famed choreographer to Michael Jackson, Janet Jackson, and Beyoncé.
In 2010, Tiffany turned her passion for music into a DJ career, spinning at exclusive parties in Tokyo, Beverly Hills, and Miami. But her path took a deeply personal turn when the pandemic prompted her to launch Breakfast With Tiffany Show, a podcast focused on LGBTQ+ wellbeing, spirituality, and personal growth. Tiffany’s own story of transformation is nothing short of remarkable. Assigned male at birth, she transitioned after arriving in Japan, following her heart from a job in an electronics factory to dancing in a transgender cabaret. Her journey included modeling, heartbreak, substance abuse, and ultimately, a spiritual awakening. After a painful breakup and a series of personal struggles, Tiffany chose to leave her nightlife persona behind, embrace sobriety, and rediscover herself through meditation, personal development, and a silent retreat in Bali. That pivotal time led her to a new purpose: helping others find peace, purpose, and self-love.
Today, Tiffany Rossdale draws on her lived experiences and professional journey, from PR roles in Tokyo’s top venues like The Iron Fairies Ginza and PLUSTOKYO, to leading VIP nightlife tours with Airbnb, to guide others toward their own personal breakthroughs. Whether through coaching, her podcast, or public speaking, Tiffany embodies resilience, reinvention, and radiant authenticity. In 2024, Tiffany expanded her advocacy work by co-producing and hosting the documentary series We Exist, a groundbreaking project that sheds light on the lives of LGBTQIA+ individuals across Japan. Collaborating with Kyoto-based filmmaker Felicity Tillack, Tiffany traveled from Tokyo to rural regions like Matsuyama in Ehime Prefecture, conducting in-depth interviews with activists, academics, cabaret performers, and even Shikoku’s first transgender city councilor.
Monika: Hello Tiffany! Thank you for accepting my invitation.
Tiffany: Thank you, Monika. It’s truly an honor to be featured on your blog. I’ve followed many of the incredible stories you’ve shared over the years. Some of those amazing women I even know personally. It’s so inspiring to see how dedicated you are to uplifting trans voices from around the world, especially those whose stories often go unheard. I’m incredibly grateful for your work and so happy to be part of it.
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| "Japanese people were so kind and patient with me." |
Monika: I’ve had the pleasure of meeting and interviewing many inspiring sisters, but your story truly stands out as one of the most captivating. Let’s begin at the beginning. Could you tell me about your life growing up in the Philippines?
Tiffany: That’s such a beautiful thing to hear… thank you, Monika. Growing up in the Philippines was a mix of beauty and hardship. My early years were full of chaos and uncertainty, almost like something out of a teleserye, very dramatic, painful, and yet somehow still filled with moments of joy. When I was just six, my mother had to leave for Japan to work, hoping to provide us with a better life. My siblings and I were left behind and shuffled between relatives. Unfortunately, we faced mistreatment and abuse during that time.
Eventually, my father took us in, even though he could barely afford to support us. We moved into a small apartment in one of Manila’s slum areas, but despite the poverty, it was the first time we truly felt loved and safe. That period was transformative for me, it’s when I started becoming more aware of who I was. At school, I was often bullied for being too “girly,” but that led me to find my tribe, other kids like me who saw me for who I really was. We formed a dance group and began performing at local town festivals. We’d enter competitions, and more often than not, we’d win! Looking back, those performances were more than just fun, they were moments where I felt seen, confident, and free to express myself.
Monika: What brought you to Japan in the first place? Was it love, adventure, or a twist of fate?
Tiffany: I would say it was a beautiful twist of fate and a blessing, really. I was very lucky that my mother invited me to come live with her in Japan. She had married a Japanese man, who later became my stepfather and he’s truly one of the kindest, very supportive people in my life. At that point, I had barely known my mother. She left for Japan when I was young, so we never really had the chance to build a relationship. Coming to Japan felt like a second chance to finally get to know her and experience what it’s like to live as her daughter.
But there was another part of me that was deeply curious about Japan for a different reason. Growing up in the Philippines, I used to watch all these glamorous beauty pageants, and I was always captivated by the stunning Filipina trans women who competed. So many of them would mention that they worked in Japan and that’s where they had their transitions. It sparked something in me. I was intrigued, inspired, and I wanted to understand more about that path. So yes, it was a mix of reconnecting with my roots, seeking belonging, and also discovering the possibilities of becoming more fully me.
Monika: I visited Japan once and completely fell in love, with the culture, the people, and the breathtaking nature. But I also remember feeling incredibly lonely, mostly because I couldn’t speak the language. What were your early days in Japan like? Did you face similar challenges?
Tiffany: Oh absolutely, I relate to that feeling so much. When I first arrived in Japan, I didn’t realize just how important learning the language would be. I thought, “Well, I speak English, maybe that’s enough to get by.” But I quickly found out that wasn’t the case at all. Soon after arriving, my mom asked me if I wanted to continue my college degree in Japan or start working. I chose to work, mostly because I didn’t feel confident navigating a university environment without knowing Japanese. But what felt like a limitation at first actually became one of my biggest motivators.
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| "Even when I started pursuing modeling, I kept my gender identity hidden." |
Tiffany: Not being able to communicate pushed me to really learn the language. I knew I had to figure it out if I wanted to build any kind of life here. Especially as I started making Japanese friends and dating Japanese men who didn’t speak English. I had no choice but to immerse myself. I learned by having real conversations, asking questions, making mistakes, and just being willing to try.
Japanese people were so kind and patient with me. Many of them helped me along the way. I’m really proud of myself for doing the work, because learning the language opened so many doors for me, not just professionally, but also emotionally and socially. It allowed me to feel more rooted, more independent, and truly connected to the community here. It’s been one of the most empowering parts of my journey.
Monika: After arriving in Tokyo in the late 1990s, you quickly rose to become one of the city’s most iconic socialites, curating dazzling fashion events and luxury parties through your Tokyo Fashionista brand for five-star hotels, top fashion labels, and mega-clubs. What inspired you to launch this glamorous venture?
Tiffany: Thank you so much for that recognition, Monika. It truly means a lot. But this didn’t happen overnight. It took me many years to rise in Tokyo’s nightlife scene and to be seen as one of its most recognized figures. In the beginning, I was navigating this glamorous world while still hiding a big part of who I was. I wasn’t publicly out as a transgender woman, and I carried a lot of shame around my identity. At the time, I didn’t believe that society, especially in Japan, would accept me if they knew the truth.
For years, I worked in a cabaret show club where I performed on stage. These kinds of spaces existed in the underground nightlife scene. People would come, watch us perform, be amazed, and applaud - but it ended there. We were entertainers, nothing more in their eyes. There was a very clear unspoken rule - if we saw those clients in public, we were not to approach or greet them. I didn’t understand why at first, so I tried saying hello a few times, only to be completely ignored or met with blank stares. It was confusing, but it also taught me how the world saw us back then - fascination in the dark, silence in the daylight.
Monika: That must have been incredibly isolating. How did you eventually find the courage to step into the spotlight as your full self?
Tiffany: Even when I started pursuing modeling, I kept my gender identity hidden. I feared that being openly trans would cost me every opportunity. So I kept it quiet. Creating Tokyo Fashionista was my way of reclaiming my place, not just behind the scenes as a producer, but also on the runway, being visible in my full light. I allowed myself to be both creative and seen. That event opened many doors for me. Not just in modeling, but in building more business relationships and trusts from people. It became more than just a brand, it was a celebration.
Monika: And speaking of glamour, you didn’t stop at organizing the parties, you took over the DJ booth too! What drew you to music, and how did you make the leap from hosting to spinning tracks yourself?
Tiffany: Yes! And I still DJ to this day. Especially now that I’m doing a bit of a comeback after taking a break during the pandemic. Music has always been a huge part of my life. Back in the Philippines, I was glued to MTV. I’d watch music videos for hours and follow all my favorite artists. I was absolutely obsessed with the Spice Girls! They were my everything! Their energy, style, and message of empowerment really resonated with me. And of course, I’ve always loved dancing, so music was my natural language.
Monika: That passion definitely shines through! But how did you go from loving music to actually stepping behind the decks?
Tiffany: When I launched Tokyo Fashionista, I found myself surrounded by international DJs, some I met during my travels, and many others through the parties and events I organized. I became really close with some of them, and one day, I asked one of my resident DJs to teach me a few basic skills. As soon as I touched the decks, I was hooked!
Now, I just want to admit that I’m not a technical pro. I don’t do complex mixing or produce original tracks. But what I am great at is selecting the perfect tunes to light up the energy in a room. I know how to read the vibe, keep people dancing, and make every moment feel unforgettable. And the best part is I get to dance with everyone while doing it! For me, it’s never about perfection... it’s about joy, connection, and having fun. That’s what music is all about.
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| "The idea wasn’t just to highlight the glitter and glamour often associated with queer life." |
Tiffany: Thank you so much, Monika. We Exist was born from a place of deep longing… for visibility, for connection, and for healing. Living in Japan as a transgender Filipina, I know what it feels like to navigate life with layers of identity that are often misunderstood or completely invisible. I’ve met so many incredible queer individuals over the years whose stories are powerful but rarely heard, even within the LGBTQIA+ spaces here. I felt a responsibility to do something and to create a platform where our stories could be seen, heard, and honored.
The idea wasn’t just to highlight the glitter and glamour often associated with queer life. It was to have meaningful conversations. I wanted to show the real lives behind the labels: the struggles, the quiet victories, the joy, and the resilience. I wanted to capture the diversity of our community and how we show up in different spaces.
Monika: That’s such a beautiful vision. But being both the creator and the one in front of the camera must have brought its own challenges. What was it like emotionally to share so much of yourself in the process?
Tiffany: Stepping into the role of producer, host and storyteller was incredibly emotional for me. I wasn’t just asking others to be vulnerable, I had to be just as open, just as raw. It wasn’t always easy, but it was healing. It reminded me that our stories no matter how big or small can change hearts, minds, and even policy. This project became a love letter to our community. A reminder that we exist, we belong, and we deserve to be seen not as “others,” but as fully human.
Monika: In the series, you speak with such a wide range of people, activists, professors, cabaret hostesses, Shikoku’s first transgender city councilor, bar owners, their patrons, and everyday folks on the street. Were there any stories that touched you on a deeper level or left a lasting impression?
Tiffany: Every story in We Exist holds so much value, and every person I spoke with brought something unique and powerful to the table. But if I had to highlight one that touched me on a deeply personal level, it would be my conversation with Watanabe Hiroyuki, Shikoku’s first transgender city councilor. Her presence, her work, and her courage are truly inspiring. She’s not only breaking barriers, she’s creating space for others to follow. The way she uses her lived experience to advocate for our community gives me so much hope. She’s the kind of representation we desperately need in politics… not just someone who talks about inclusion, but someone who embodies it.
What made our conversation especially meaningful is that I chose not to do a pre-interview with her. I wanted our interaction to be as real and spontaneous as possible, to capture the genuine energy between us. And that’s exactly what happened. When you watch that part of the film, you’ll see two trans women, both of us with histories in the cabaret scene, sharing stories, exchanging laughter, and recognizing ourselves in each other. It was a moment of deep connection, and I left feeling more affirmed in my journey. Her story reminded me that our pasts don’t limit us, they shape us into powerful voices for change.
Monika: Thailand is often celebrated as one of the most trans-friendly countries, especially with its supportive healthcare services for transgender women. I’m curious, how would you compare that to the situation for transgender women in Japan? What are some of the key differences you’ve noticed?
Tiffany: I absolutely agree! Thailand has long been a leader when it comes to gender-affirming healthcare. I had my SRS surgery there many years ago, and the experience was incredibly positive. I felt safe, seen, and well taken care of throughout the entire process. It’s no surprise that so many trans women from around the world choose Thailand for their medical transitions.
END OF PART 1
All photos: courtesy of Tiffany Rossdale.
© 2025 - Monika Kowalska
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