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?
Penny: Before I transitioned, my wardrobe was black t-shirts and jeans. When I started dressing femme, I scrapped everything and began from zero. I wanted to discover what I liked without inherited rules or expectations. That meant buying a lot of things that were cute in theory but awful in practice. Especially when you’re almost 40, and trying on things most women grew out of in their twenties. But through trial and error I rebuilt my style into something intentional and honest. I still love a great pair of jeans and a black t-shirt, but now it’s a choice, not a default.
As a tall, lean woman, I gravitate toward long vertical lines, monochromatic looks, A-line dresses, and anything that creates a waist. I’m a dramatic natural if you follow Kibbe body types. I would call my style casual-street-punk-preppy-chic. A mixture of Tannis from Letterkenny, Stevie from Schitt’s Creek, and Daria from…Daria.
Monika: Do you love playing around with makeup, or is it more of a “throw on the basics and go” kind of vibe for you?
Penny: These days it’s mostly a “throw on the basics and go” kind of thing. I’ve grown to appreciate a less-is-more approach. That said, it didn’t start that way. The first year, I was so lost reading articles, watching videos, trying to understand how other redheads approached makeup, and feeling overwhelmed by the sheer amount of products out there. My first trip to Sephora I spent almost four hours (not joking) looking at everything, comparing, and trying to make sense of it all. Now that I’ve found what works for me, makeup feels less like a project and more like a small way of taking care of myself before heading out into the world.
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?
Penny: I’ve never been particularly good at accepting compliments. Before transition, I had very low self-esteem when it came to my appearance, and I honestly preferred not being noticed at all. That invisibility felt safer, and I struggled to accept any affection because I didn’t believe I was worthy of it. Now, as I grow into a version of me that feels right, compliments land differently. They still catch me off guard, but they don’t bounce off, I latch onto them as points of affirmation.
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| "Love has shaped every part of my life and this journey more than anything else." |
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?
Penny: Definitely, and it’s a double-edged-sword. On one hand, you’re told that you don’t owe anyone femininity, that womanhood isn’t a look or a performance. And that’s true in a perfect world. But then you step outside and get harassed for looking trans, and suddenly it’s not about expression anymore, it’s about safety.
For trans women, and increasingly for masculine cis women, presentation becomes everyone else’s business. If you look “manly”, people feel entitled to interrogate you, to decide where you belong, to dictate that you should be treated less than. There’s this collective paranoia about “being fooled,” mixed with a self-righteousness that feels ignorant and violent.
Early in my transition, it felt like I had to balance the scales. I leaned hard into femininity with dresses and heavy makeup, not because it was true to me, but because I needed people to see past the masculinity. It was exhausting and infuriating because no woman should have to prove her womanhood just to move through the world without fear.
Monika: When I came out at work, my male co-workers suddenly started treating me as if my transition had lowered my IQ. Did you experience a similar shift in how people perceived your intelligence or competence?
Penny: Yes, and it’s such a strange thing to try to explain without sounding paranoid. But the shift is real, and it’s subtle. I started noticing my decisions being questioned more often, my ideas second-guessed, sometimes ignored altogether. Nothing overt enough to call out, just enough to make me start doubting myself, creating this erosion of confidence from being treated as less capable, over and over again. Intelligence and femininity have no correlation, but here I am witnessing this belief in real-time, that becoming more feminine has made me inferior in some way.
Monika: What was the most surprising part of your transition, something you never expected, whether good or bad?
Penny: The most surprising part of my transition is that I didn’t lose a single person. I had spent decades carrying so much shame, convinced I was hiding something dark and unlovable. Coming out meant sharing what I once thought were the worst parts of me, naming fears I’d held secret for years. Learning I was trans taught me how to love myself, but what I never expected was how readily others would love me too. I had braced for loss, for distance, for silence. Instead, I found acceptance. And that has been one of the most healing surprises of all.
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| "If the first chapter was about becoming, the next one is about living." |
Penny: Love has shaped every part of my life and this journey more than anything else. My wife has been my biggest supporter through all of it, steady, patient, unwavering in a way that still humbles me. My parents, too. The people who mattered most to me showed up when it mattered most, without conditions or hesitation.
That kind of love changes you. It rewrites what you thought was possible. I used to carry this fear that being honest about who I am would cost me everything, that love would be the first thing to disappear. Instead, it stayed. It deepened. Knowing that I could be fully seen and still loved has been the most profound affirmation of my life. Love has been the thing that softened the hardest parts of this process and made the joy feel real. Quite honestly, love is what made life worth continuing to live for me. It gave me something to move toward, something to trust, and something to build my happiness around.
Monika: Finally, what’s next for Penny? What dreams and goals are you working toward now?
Penny: What’s next feels less like a dramatic pivot and more like a deep exhale. For the past few years, transition has taken up nearly all of my mental and emotional bandwidth. Every decision and every step scrutinized, like I was constantly asking myself if I was doing it right. But now I’m finding clarity and a surprising amount of levity in simply existing as myself. This interview actually feels like a natural closing to the first chapter of my life as a woman.
I’m still transitioning, of course, but now I get to live fully inside it. I’ve been intentionally selfish in the most necessary way, and now I’m excited to shift that energy outward, especially toward my wife, who has held so much space for me. It feels good to finally be able to show up for her more fully. I also want to deepen my connection to the local trans and queer community, not just as a participant but as a contributor. I’m drawn to the idea of creating a space where people can gather, feel seen, feel at home, and know they belong to something larger than themselves. Community was what made my own transition survivable, and I feel a responsibility and a genuine desire to offer that to others.
If the first chapter was about becoming, the next one is about living, building, and sharing the light I’ve worked so hard to find.
Monika: Penny, thank you so much for sharing your journey and insights.
Penny: Thank you for the opportunity to reflect on my experience, and to join this collection of powerful voices!
END OF PART 2
All photos: courtesy of Penny.
© 2025 - Monika Kowalska
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