Letting Go Isn’t Giving Up

What a closet full of clothes taught me about shame, self-worth, and starting over.

After publishing this week’s blog post on The Well Dressed Life — What to Do With Clothes That No Longer Fit Hanging in Your Closet — I heard from so many of you.

The comments, messages, and emails poured in. Some said it was exactly what they needed. Others said it made them cry. A few shared they were finally ready to face what was hanging in their own closets — and what it represented.

I wasn’t surprised the post resonated, but I was struck by how deeply it did.

For most of us, the clothes that no longer fit aren’t just clutter. They’re holding our shame. Our guilt. Our grief. They represent the version of ourselves we think we should get back to, even if that version was never truly at peace.

So today, I wanted to go a little deeper — to share the full story behind that post. The emotional spiral that filled my closet. The moment I realized I didn’t even want to get back to the person I used to be. And how letting go of a pile of clothes became the first step in finally showing up for myself again.

How I Got There

When I look back on that chapter — when I was gaining weight quickly — it’s obvious now that I was in a terrible place. Everything felt out of control, like I’d been spun around too fast and then set loose, stumbling through a kind of emotional dizziness. (Does that make sense? Because that’s how it felt.)

My closet slowly filled with reminders of that spiral, and every time I tried to get dressed, I felt worse. Less like myself. More like someone I didn’t recognize. And I was furious about the series of events that got me there — some the result of my own decisions, and others just dropped in my lap.

And listen, I was gaining weight from emotional distress and midlife body changes — it was a recipe for disaster. My hormones were shifting, my stress was maxed out, and my coping mechanisms weren’t great. The physical changes were real, but the emotional toll was even heavier.

In the beginning, I still tried to force it. Not willing to accept reality. Literally. I would physically push my body into clothes that were wildly too small — jeans that cut into my stomach, sweaters that pulled across my chest. It was so unkind. So devastating. Every morning became a fresh reminder of the chaos I was living in.

And then one day, after a breathless try-on session — you know the kind that leaves you red-faced, sweaty, and actually out of breath — I had two realizations that changed everything:

First, that my morning routine of either squeezing into clothes or staring at ones that didn’t fit was, plain and simple, emotional abuse. I was flogging myself before the day even started. And I knew better. For years, I’d told my clients to remove anything that didn’t currently fit. Not throw it out if they didn’t feel ready — just move it out of your primary closet. Put it in a box, a bin, somewhere out of sight. Because you shouldn’t start your day running a mental record of: that doesn’t fit, that doesn’t fit, I can’t wear that.

So the fact that I wasn’t taking my own advice? That was frustrating.

And then came the second — more important — realization:
I didn’t even want to be the girl who used to fit into those clothes.

Because she wasn’t happy either.
In fact, she’s the one who got me into the state I was in.

She was tired. She was pretending. She was disappearing into expectations that didn’t reflect who she really was.
She didn’t know how to rest. She didn’t know how to say no.
She didn’t even know herself.

And she certainly didn’t know how to be kind to herself.

So why was I holding her up as the version I needed to get back to?

The Thing About Not Caring

This isn’t just about clothes. It’s about coming back to yourself.

And want to be clear: this is my experience. I’m not here to project or prescribe — just to share what’s been true for me.

One of the greatest gifts of getting older is that we finally stop caring about things that never really mattered. We let go of perfectionism, people-pleasing, and performance. We stop dressing for the male gaze. We stop seeking outside validation. That kind of freedom is powerful — and necessary.

But I also hear a lot of women in midlife and beyond say things like, “I just don’t care about all this anymore” — the clothes, the beauty routines, how we show up physically.

And I get it. I really do.

It’s exhausting to feel like your worth is tied to your appearance or the number on a tag. Letting go of that pressure is a vital part of healing.

But here’s where I want to be very clear:
This isn’t about getting smaller. It’s about getting softer — with ourselves. Kinder. More accepting.

My story isn’t about losing weight. It’s about losing shame.
Because self-worth has no size. Period.

For me, though, the line between freedom and checking out got really blurry.

I didn’t just stop caring what other people thought — I stopped caring about me. My energy. My sleep. My movement. My health. My sense of style. And not in a peaceful, “this doesn’t define me” kind of way, but in a burned-out, “I’m too tired to even try” kind of way.

And while I’m grateful I let go of the wrong things, I’ve realized something really important:

I want to care. About me. Just as I am.

I want to show up for myself — physically, emotionally, mentally. I want to dress in a way that reflects who I am now. I want to feel good in my clothes and at home in my body — this body.

I want to be the main character in my own life — especially now, as my kids grow up and I finally have space to ask, Who am I outside of them?

And I want to feel beautiful. I want my kids to remember me as their beautiful mom — not because I was always done up, but because I had a sense of style that was mine. One that made me feel like myself. One that might inspire them to care for themselves, too.

Is that crazy? Maybe. But I don’t think so.

Because you know what? Dressing well — even if it’s just jeans and a button-down — wearing makeup, taking care of myself... it doesn’t feel superficial anymore.

It feels empowering.
It feels like honoring the version of me I’m becoming.
It feels like remembering I get to be the main character now.

Letting Go Was the First Step

The truth is, I didn’t reclaim my confidence overnight. I didn’t do a dramatic closet purge or suddenly bounce back. I started small — gently — and with a lot of grace for the woman I had become.

I let go of a few things at a time, tucked others away so I didn’t have to see them, and bought a few new pieces that fit my current shape — pieces that honored it.

And here’s the thing: letting go of the clothes I kept out of guilt, shame, or “someday” thinking was the first step — in a long series of steps — in starting to care again.

Letting go helped me stop spiraling and start reconnecting.

It was also the first truly kind thing I had done for myself in a long time.
Because it meant putting an end to the brutal daily routine of self-flogging — standing in front of the mirror disgusted with myself, feeling defeated before the day even began. It was me saying, “This ends here.”

It wasn’t about giving up. It was about moving forward.

And slowly, things began to shift. The shame lifted. My closet became a place of support instead of stress. I had fewer clothes, but more options. More clarity. More confidence.

If you’re standing in front of a closet full of clothes that no longer fit, please know:

You’re not broken. You’re not failing. You’re just evolving.
And letting go might be one of the kindest things you ever do for yourself.

Start to let go. Baby steps if you have to.

I credit that act — the letting go — as the moment I started to feel okay with who I was, no matter the shape or size.

And in full transparency, even after I got my health back — even after my body started to feel familiar again and I had replaced my wardrobe — I still had a hard time letting go.

It took me months to fully clean out my closet.
And I’m an actual expert.

Because it’s hard.

But we can do hard things — and it’s a little easier when you know you’re not alone.

You’re not being silly.
You’re not “crazy.”

What This Space Is About

Back when I worked as a personal stylist — whether I was in a dressing room or standing in someone’s closet — the focus was always her clothes. Her wardrobe. Her style.

But almost every time, we ended up talking about something more.

There’s something about the vulnerability that comes with getting dressed — especially in front of someone else — that brings everything to the surface. The shame, the frustration, the stories we’ve been telling ourselves for years. What started as a session about jeans or a jacket almost always turned into a conversation about life.

And honestly, that is what this space is about.

Not just clothes, but the complicated, beautiful, messy layers underneath.
The real conversations we don’t always get to have — but always, always need.

You can read the full blog post here, and if you’ve been through something similar, I’d love to hear your story below.