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Hey, lovelies.

So here’s something I never thought I’d write about, but it’s been a pretty big part of my journey lately—and it feels important to share.

For the past couple months, I’ve been wearing a sports bra under my normal boy mode clothes at work. Nothing fancy—just a basic, cheap Hanes Sports Bra from Walmart. I wanted to experiment a little. Try something small that helped me feel more feminine during the day. And especially when it was colder out, it felt easy to layer up and hide it under thicker clothes.

At first? I was terrified. Like, full-on heart-pounding nervous. What if someone noticed? What if they said something? But honestly, after a few days of doing it, it just started to feel… normal. It became part of my routine. Like any other undergarment. And even better—it worked. It made me feel softer, more connected to my femme side. And yes, a little more feminine in appearance, too—even if just for me.

Note from Michelle:
This post originally appeared on my old blog, Crossdresser Chronicles. I’ve moved it here because it still reflects an important part of my journey. Some details may be out of date, or lightly updated to fit where I am now.
👉 Read more about why I brought these posts over.

Why a Sports Bra?

A big part of why I chose a sports bra was because it felt low-risk. If anyone did notice it through my clothes, I could pass it off as a tank top or compression layer. Nothing flashy, nothing that screamed “bra” unless you were really looking for it.

And that subtlety mattered to me. Even though we have a trans person in our department and everyone’s been respectful toward them, I still can’t bring myself to be totally open about who I am. Not yet. I’m just not ready for that level of vulnerability. But this? This small step helped me feel more like me—without needing to explain anything to anyone.

What I Wore Over It

Thankfully, our department is pretty casual. I wear jeans and a company-branded t-shirt most days, and most of them are thick enough to keep everything underneath discreet. When it was colder, layering made it even easier. But even now, as the weather warms up, I still wear it on some days—just a little less often.

Most of the time, I wore it all day long. The only time I felt self-conscious was walking down the hall or going to the bathroom. I’d constantly wonder: Can anyone tell? And honestly… maybe they could. But no one ever said a word.

More Than Just Fabric

Wearing it didn’t just make me feel feminine—it helped me act more feminine, too. I found myself adjusting my posture, being more aware of how I carried myself. I’d sit differently, hold my shoulders back, even walk with a little more softness. It felt empowering and grounding at the same time. Like I was hiding something… and also finally showing something real.

I haven’t tried other bras yet. I don’t feel the need right now. If I were fully out at work and presenting as a woman? Sure, that might change. But for where I’m at today? This is enough. It’s a small, quiet step. And I’m proud of it.

A Quick Word of Caution

Now, this part is important: please be careful.

I work in a cubicle. Not everyone does. And while I’ve never had anyone comment or treat me differently, I know not every workplace is safe or supportive. If you’re considering trying something like this, please think about your environment. Do what you can to be true to yourself—but protect yourself, too. Check if your employer has any ED&I policies or protections in place. I know it sucks to have to worry about that, but I’d rather you be safe than blindsided.

The truth is, crossdressing or exploring gender expression in subtle ways—like this—is still stigmatized in some circles. And that’s not fair. But you are not alone in this. You deserve to feel like yourself, even if it has to start with something as simple as a sports bra under your work clothes.

If you do decide to try this, I recommend going with something like this Hanes Sports Bra. It’s simple, affordable, and doesn’t have frills or lace—so it can pass as a basic tank top underneath your clothes if anyone happens to catch a peek.

So yes—I wear a sports bra to work sometimes. And no, I don’t regret it for a second.


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