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Hey, lovelies.
This one’s hard to explain, but I’m gonna try.
Some days, dressing feels like the most right thing in the world. I’ll slip into something soft, cute, a little femme—and there’s this wave of calm, like I’ve finally stopped pretending. Like I can breathe.
But then I look in the mirror.
And suddenly? That comfort shatters. All I see is a boy in girls’ clothes. And it’s jarring. Not because I don’t love the clothes—but because the reflection doesn’t match the feeling. It’s like dressing unlocks a part of me… and the mirror slams the door shut again.
I talked about this more in this post about how my emotional connection has changed—but it still hits just as hard.
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 Some details may be out of date, or lightly updated to fit where I am now.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.
Cute on the Inside, Confused on the Outside
It’s a weird duality, right? Feeling amazing in something that technically “doesn’t suit you.” That’s been a huge part of my journey. I’ll have moments where I feel adorable—like I nailed the outfit, the vibe, everything. But then the dysphoria creeps in. It’s not about wanting to “pass.” It’s just… I wish the outside looked like how the inside feels.
And if that’s you too? You’re not alone, babe. I unpacked this in this piece about when dressing feels right but looks wrong, and honestly? I still revisit it when I’m struggling.
What Helped Me (Just a Little)
I started finding pieces that made me feel cute without triggering that internal “ugh.” For example: high-waisted skinny jeans, a soft wrap top, or even just a cami under my work shirt. One of my favorite go-to’s lately? This Maidenform waist cincher. It helps with posture, tucks everything in a bit, and makes me feel just a smidge more aligned.
These small wins add up. They don’t fix the disconnect, but they help me live in it a little easier.
Using Discomfort as a Guide
Eventually, that discomfort started pushing me—not away from dressing, but toward changing my life. I’m eating better, working out for a more feminine shape, and playing with makeup in boy mode too. That tiny act of putting on tinted moisturizer or a sheer gloss? It gives me something. Not full transformation. Just a whisper of her.
And that whisper is loud enough to get me through the day.
So I’ll ask you this:
When you dress, do you feel right? Or do you feel wrong? Or both?
And if it’s both—what are you doing with that feeling?
You don’t need to fix it. But you can follow it. That discomfort might be telling you something important. Something true. Something real.
🖤 Michelle
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