How Dressing Better Changed My Life

For my whole adult life, I'd felt bad about not dressing better. But I'd also refused to give up ratty clothes or buy nice ones. I'd pushed myself to obey contradictory internal commands: dress well, but don't throw things away or spend money. Finally, I broke free of the double bind.
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It's funny how we can get stuck seeing ourselves a certain way.

Until recently, I'd feel bemused whenever someone complimented my clothes. I'd smile, thinking, Oh, if only they knew ...

Sure, I might appear to be a grown woman, but inside of me lives a shy girl with outfits chosen in homage to Laura Ingalls Wilder. Lest you think I exaggerate, I include photographic evidence.


As you'd expect, I got teased about my clothes a lot when I was younger. I hardly ever felt like I was wearing the right thing, or that I was cool.

By contrast, my husband Jonathan remembers having this epiphany in middle school: "Wait a minute ... I am the cool people!" I wish I could have gone through life with this same assurance, but the realization came easier for him. After all, he never wore a sunbonnet to school.

Since then, I've moved past that shy-girl identity. But in times of stress or uncertainty, I slip into old patterns.

It's a vicious cycle: when I feel vulnerable, I shy away from dressing well. But then I feel even more insecure. And I look down at my scuffed, cracking boots and wonder why I have trouble giving myself permission to buy and wear nice things.


A few months back, my friend Brooke texted that she was cleaning out her closet. She was tossing an old, stretched-out white tee and feeling liberated. I was wearing an old, stretched-out white tee and feeling frumpy.

This did not seem coincidental. I felt a nudge in my spirit, a loving shove that said, Let the old things go, sweetie.

So I asked Brooke about her de-cluttering process (based on Marie Kondo's "The Life-Changing Magic of Tidying Up"), and I considered the idea. But I had all kinds of resistance.

I am frugal; I like to save, not spend. As a writer, it's easy for me to tune out real-world details like what I'm wearing. Sure, those falling-apart yoga pants were pretty bad, but did it matter? Since I'm self-employed, the only people I see every day are the ones at our local library.

But then even the library betrayed my desire to avoid change. As I was browsing, I picked up a book called Change Your Clothes, Change Your Life by George Brescia. This passage struck a nerve:

"What in your belief system allows you to operate without [these] basic wardrobe necessities? ... We tend to bind up our identities in our clothes, so ... we think of it as some kind of insurmountable emotional problem or an innate character flaw -- 'I'm just not a person who has ever dressed well ...' Would you ever say that about your kitchen? 'I'm just not a person who can keep a cutting board ... ' See how absurd that sounds?"

I did see. For my whole adult life, I'd felt bad about not dressing better. But I'd also refused to give up ratty clothes or buy nice ones. I'd pushed myself to obey contradictory internal commands: dress well, but don't throw things away or spend money.

Finally, I broke free of the double bind. I cleaned out my closet and made a list of the basics I lacked. I kept clothes that made me feel joyful and confident; I tossed or donated items that made me feel like a beggar in a Dickens novel.

There were a surprising number of unlovely freebies: the stained running shirt, the zebra-striped shorts. Every time I wore them, I had to tune out the inner voice that said, Ugh, I don't like this.

There was sadness in letting some things go, but there was also a tremendous rush of energy. Facing up to the truth about my clothes made me feel great, whereas staying in denial depleted me.

That's the thing about decluttering: it's a tactile truth-telling exercise. For me, cleaning a closet is not about being wasteful or becoming a fashion plate. Instead, it's about practicing self-honesty.

When I get real about which clothes look good, I tap into that honesty in other areas. It's transitive. Admitting that a shirt's life is over empowers me to see what else in my life is over, too.

This is a game-changer for those of us who spend our days wrapped up in stories of what was or what might have been.

And paradoxically, wearing clothes that fit and look good frees me to focus on other people. When I go running in athletic clothes that aren't rags, I am more likely to be friendly. Ever since I made the resolution to dress better, I've felt the weight of self-consciousness lifting.

With that in mind, my current task is to acquire carefully-selected new items. Unsurprisingly, I feel guilty about this, because part of me still believes that it's "selfish" to purchase clothes.

Spending is hard for me in general, but certain purchases are more stressful than others. I buy books and notebooks with relative ease, because I'm comfortable thinking of myself as a writer, a "brain."

It's harder to buy nice clothes, because I struggle with my status as an embodied human. When I do manage to buy leather boots, it's a victory. It's me honoring my body, and the real life I've been given.


When I chose to care for my body by dressing better, that decision rippled outward. When I tossed my shabby clothes, I discovered a decreased tolerance for shabby behavior. I stopped making excuses and started making changes.

Simply getting rid of the duds in my closet has made a huge difference. I do laundry more often, but it's worth it. And when I wear the nicer clothes I already have, something shifts. I begin to value myself.

That's why I don't mind telling people about my resolution to "dress better." I don't mind if they laugh, because I'm laughing too.

It's funny to look at the old limits I put on myself, to see how flimsy they turned out to be.

This piece first appeared on A Wish Come Clear, a blog devoted to helping you choose love, lose fear, and find home. Visit and receive free copies of Caroline's three digital books, all designed to bring you back to what matters most.

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