Letters to My Former Self

A Reader Writes: 'I haven't worn a dress for three years.' Here's my reply.

2026-05-24 18:31 42 views
A Reader Writes: 'I haven't worn a dress for three years.' Here's my reply.
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Verdict

You don't have to love your body to let it wear a dress.

She wrote me last Tuesday. Short email. No small talk.

"I haven't worn a dress for three years. Not since I gained the weight. I look at them in stores and think — who would want to see me in that? I'm not looking for a pep talk. Just wondering if you've been there."

I read it three times.

Because yes. I have been there.


The last dress I wore before my body changed

Black knit dress on hanger with mirror and leggings on white table.

It was navy blue. Wrap style. I remember because I spilled coffee on it the morning of a friend's wedding and spent twenty minutes blotting it with a wet paper towel.

That was four years ago.

After the steroids, after the forty pounds, I couldn't even look at dresses. Not because I didn't like them. Because I didn't want to feel that thing — you know the one — where you try it on, turn sideways in the mirror, and immediately start a list of every part that looks wrong.

So I just stopped.

Jeans. Sweaters. Leggings. The same three outfits on repeat.

I told myself I was being practical. But really? I was hiding.


So here is what I want to say to her. And to you, if you need it.

First: You don't have to love your body to wear a dress.

I don't say that to be dark. I say it because everyone acts like you need this big breakthrough moment where you look in the mirror and finally see a goddess. That never happened to me. I still have mornings where I pull on a shirt and think ugh.

But I wear dresses now anyway.

Not because I feel perfect. Because I got tired of being scared of a piece of fabric.

Second: Start with the dumbest dress you can find.

Not expensive. Not fancy. Not something you'd wear to a wedding. I'm talking about a $25 t-shirt dress from Old Navy. Stretchy. No zipper. No tags that dig in. The kind of thing you could wear to the grocery store and no one would notice.

I bought mine in heather gray. Ugly color. But I wore it around my apartment for an afternoon. Then to get the mail. Then to Target.

No one stared. No one said anything. The world did not end.

Third: The first time will feel weird.

You'll tug at the hem. You'll cross your arms over your stomach. You'll wonder if everyone is looking at your thighs or your arms or whatever part you're most worried about that day.

That's fine. Let it be weird.

I wore my gray dress for two hours the first time. Then changed back into sweatpants. Progress is not a straight line.


What I wish someone had told me

A dress is not a reward for being thin. It's not something you earn after you lose the weight or fix the parts you don't like.

It's just clothes.

And you are allowed to wear clothes that feel good — or even just feel fine — without earning them first.

That reader? She wrote me back yesterday.

Said she bought a black knit dress from Target. Tried it on at home. Didn't take it off for an hour.

She said, "I didn't feel beautiful. But I didn't feel horrible either. I think that's enough for now."

Yeah. That's enough.

You haven't worn a dress for three years. Okay. Maybe today you try one on in your bedroom. No photos. No audience. Just you and some stretchy fabric.

And if it doesn't work? Take it off. Try again next month.

The dress isn't going anywhere. Neither are you.