Monika: That sounds like such an intense emotional burden to carry. Was there a turning point for you, when you began shifting from fear to self-acceptance?
Tiffany: Over time, I realized that this constant striving to fit into society’s narrow definition of womanhood was exhausting and it wasn’t rooted in self-love. It was rooted in fear and shame. What gives me hope now is seeing how this generation is shifting that narrative. More and more people understand that there’s a beautiful spectrum within the trans community, and we don’t all have to fit into the same mold. We are women. We are nonbinary. We are who we say we are and that is enough.
So while I still feel the pressure sometimes (we’re human, after all), I remind myself that my worth isn’t based on how others perceive me. My journey is valid. My identity is mine. And the more I embrace that, the more empowered I feel.
Monika: How would you describe your personal style? Do you follow any specific fashion trends, or do you have go-to outfits that make you feel confident?
Tiffany: I love fashion! For me, it’s an extension of my creativity, identity, and mood. It’s one of the skills I’ve embraced to express my uniqueness and sense of self. I always feel a little extra affirmed when people compliment my style, and I’ve been told many times that I have a great eye. Not only for what’s trending, but also for looks that could become a trend.
I do love dressing up and playing with different aesthetics, but nowadays I don’t shop for clothes as much as I used to. I’m grateful to have friends who pass along beautiful pieces they no longer use, and I’ve also collaborated with fashion brands that gave me high-quality clothing. Some of those pieces are still staples in my wardrobe even years later.
Monika: That sounds both stylish and intentional. Has sustainability become a key part of how you approach fashion now?
Tiffany: Definitely. Sustainability matters to me, so I try to live and dress in a more eco-conscious way. I think fashion can be luxurious and expressive without being wasteful.
Lately, one of the styles I’ve fallen in love more with is the kimono. There’s such depth and artistry in how they’re worn. I’m fortunate to have a personal sensei who’s teaching me how to dress in a kimono properly. It’s incredibly intricate and requires so much care and attention. But when I wear one, I feel empowered and I feel so connected to the elegance of Japanese culture, and to my own femininity in a very special way.
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| "My daily vibe is more about healthy, radiant skin." |
Tiffany: As a performer for many years, makeup was a huge part of my world. I loved experimenting with bold looks, dramatic lashes, and all the fun that comes with transforming your face into art. It was one of the ways I expressed different versions of myself on stage. But now that I don’t perform every night, makeup has become more of a special-occasion ritual. I still love wearing them as it makes me feel glamorous and empowered.
But I’ve also grown to prioritize skincare over full glam. These days, I go makeup-free most of the time to let my skin breathe and glow naturally. So yes, I still enjoy playing with makeup when the moment calls for it, but my daily vibe is more about healthy, radiant skin and feeling good from the inside out.
Monika: By the way, do you like being complimented on your looks? Do you find it easy to accept compliments, or do you struggle with believing them?
Tiffany: That’s such an interesting question. When I was working in the nightlife entertainment industry, I really did put a lot of effort into looking my best especially on stage. I saw it as part of the performance, part of the magic. And most nights, I was showered with compliments on my beauty, my outfits, my presence. I won’t lie, I appreciated those moments. Being seen and admired felt affirming in many ways.
Monika: And what about negative comments, have they affected the way you see yourself?
Tiffany: Absolutely. Not all comments were kind. There were times when customers would say hurtful things like, “You still look like a man,” or “You need more hormones to look feminine.” And even if they said it as a joke, it stung deeply. Those words stayed with me longer than the compliments. They chipped away at my confidence and made me hyper-aware of the parts of me I felt didn’t “measure up.”
I had to do a lot of inner work to unlearn those experiences. I realized that so many of us are conditioned to tie our worth to how we look and worse, to how others perceive us. What helped me heal was shifting my focus from how others see me to how I see myself. I began embracing all parts of my humanity, not just the polished or “feminine” parts, but even the features I used to criticize or want to change. Now, when I receive a compliment, I allow myself to accept it with gratitude but I no longer depend on it for validation. I’ve learned to love myself from the inside out. That’s been the real transformation.
Monika: Did you ever feel pressure to meet a certain ideal of femininity, like I did by trying to look like the women around me?
Tiffany: Yes, absolutely. I felt that pressure deeply especially working in the nightlife entertainment industry where appearance was everything. Most of the women I worked with on stage were incredibly competitive, and to survive in that environment, I had to be as well.
I believed that if the club owners didn’t find me attractive or if I wasn’t being requested by clients, then it must mean I wasn’t feminine enough. That kind of thinking pushed me toward more surgeries and more hormones, always chasing an ideal that never seemed quite within reach. We also earned tips, and on nights when I didn’t get as much as the other girls, I would spiral into self-doubt, thinking, What’s wrong with me? Am I not pretty enough? Not passable enough?
Monika: Was there a specific moment that made you start questioning that definition of femininity?
Tiffany: There was a Filipina trans woman I became friends with, someone I looked up to at the time who really influenced the way I saw myself. She had very strict ideas about femininity and being “clockable.” We traveled together to the U.S., and if someone even suspected I was trans, she would get upset with me. She’d shame me, lecture me about how I needed to “step it up” and be more feminine. I have to be more like her. That experience stayed with me for a long time.
But eventually, I realized how toxic that mindset was. I had to unlearn all of it. I had to make peace with my body, my identity, and my expression of femininity not someone else’s. Femininity, like gender, is not one-size-fits-all. Now I know that my worth isn’t tied to how well I “pass.” It’s in how true I am to myself. And that’s the kind of example I want to set for others in our community.
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| "I would love to write my own memoir one day." |
Tiffany: After my SRS, I truly believed I had reached a point where I could live as a "fully" woman and never be clocked as trans again. I thought that if I looked the part, I could finally leave the past behind and no longer have to explain or justify my existence. But what I didn’t expect was how mentally and emotionally exhausting it would be to live in hiding.
I found myself pretending, sometimes even lying about who I was, just to maintain this image of womanhood that I thought society expected of me. I had admired a trans woman who seemed to have the perfect life: she married a man who didn’t know she was trans, and she never came out. I thought maybe I could live like that too.
Monika: What helped you move from that place of hiding toward living more openly and truthfully?
Tiffany: I met other trans women who had made the same choice to never disclose their history and just live as women, quietly. But over time, I realized that hiding such a big part of who I am wasn’t freedom. It wasn’t healing. In fact, it created a deep sense of disconnection from others, and from myself. What surprised me most was that, even after “completing” my physical transition, I still didn’t feel whole. Because wholeness comes from radical self-acceptance.
Now, I choose to live in truth. And while it’s not always easy, it’s liberating. I’ve learned that being visible as a trans woman is not a limitation, it’s a powerful act of reclaiming my voice and my story.
Monika: Many trans women are writing their memoirs these days. Have you ever thought about writing your own book, and if so, what would its central message be?
Tiffany: Absolutely, I’ve thought about it many times. It truly amazes me that we’re living in a generation where writing a memoir is so much more accessible. Our voices, stories, and experiences can finally be documented and shared in our own words. It’s such a powerful way for our truths to be heard, and more importantly, understood.
I would love to write my own memoir one day, and I trust that when the right timing comes, I’ll be ready to tell my story in full. There’s so much I want to share not just about being a trans woman, but about healing, reinvention, resilience, and choosing authenticity even when it’s hard. Books have always been a source of inspiration and reflection for me. And I believe a memoir is more than just a collection of memories. It’s a tool for education, connection, and empowerment.
Monika: Finally, what’s next for Tiffany? What dreams and goals are you working toward now?
Tiffany: Right now, I’m stepping into a new chapter that really excites me. I’ve started studying acting, and I’ve discovered how much I truly love it. There’s something so powerful about being able to express raw emotion, to embody a character, and to tell stories through performance. It’s therapeutic and exhilarating all at once. I’m incredibly proud to share that I’ll be appearing in an upcoming feature film, playing one of the main characters. It was such an honor to be part of the project, and once it’s released, I hope it opens more doors and shows others a glimpse of my potential as an actress.
Beyond that, I’ll continue to pour my heart into my advocacy through The Breakfast With Tiffany Show podcast and our We Exist documentary series. Both platforms are dedicated to amplifying voices within our community, sparking meaningful conversations, and creating visibility where it’s so much needed. I’m still dreaming big and always will. Whether it’s through storytelling, performance, or simply being present in spaces that haven’t always welcomed people like us. My mission remains the same and that is to live boldly, truthfully, and in service of something greater than myself.
Monika: Tiffany, thank you so much for sharing your journey and insights.
Tiffany: You're very welcome, Monika. Thank you for giving me the space to share my story so openly. Thank you for using your platform to highlight trans women stories from around the world. And to now be part of this sisterhood you’ve built is truly an honor. I hope my words reach those who need them most. Those still finding the courage to live their truth, or those simply wanting to understand our lives more deeply. And I hope this conversation inspires continued compassion, curiosity, and visibility for our community.
Tiffany's media links:
LinkedIn: link
Official Website: link
Instagram: link
Facebook: link
Breakfast With Tiffany Show Podcast: link
We Exist Documentary IG: link
END OF PART 3
All photos: courtesy of Tiffany Rossdale.
© 2025 - Monika Kowalska
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