In Which I Dare To … Dress Better.

It’s funny how, without meaning to, we can get stuck seeing ourselves a certain way.

Until recently, I’d feel bemused (and even confused) whenever someone complimented me on my appearance or clothing choices. I’d smile and say thank you, but still, a voice inside would say, Oh, if only they knew …

Sure, I might appear to be a grown woman wearing a nice dress, but inside of me lived a shy, vulnerable girl who chose to wear prairie dresses and cameos in homage to her early literary hero, Laura Ingalls Wilder. Lest you think I exaggerate, I will include photographic evidence.

Grade School ... not daring to dress better

Grandparents’ Day in elementary school

As you’d expect, I got teased about my clothes a lot; even my good friends thought they were weird. I hardly ever felt like I was wearing the right thing, or that I was cool.

By contrast, my husband Jonathan remembers looking around his middle school, wondering at his peers’ collective obsession with being ‘the cool people’. Then he had this epiphany: “Wait a minute … I am the cool people!” I wish I could have gone through life with this same assurance, but then, I’m guessing that this realization came easier for him. After all, he never wore a sunbonnet to school.

In many ways, I’ve moved past that shy-girl identity. Charlotte Bronte is my homegirl forever, yes, but I don’t need to dress like her. I’m learning to be confident in my own shoes, rather than pretending to be someone else. But in times of stress or uncertainty, I slip into old patterns.

It’s a vicious cycle: when I feel vulnerable, I don’t want to be seen, so I shy away from dressing well. But then I feel even more insecure, which makes me want to hide. And I look down at my scuffed, cracking boots and wonder why I have trouble giving myself permission to buy and wear nice things.

Grown up Caroline, daring to dress better

Photo shoot for new business website (coming soon!)

In short, I have some baggage in this area. (Don’t we all?) Fortunately, I have brave friends who are always venturing out of their comfort zones. A few weeks ago, my friend Brooke texted that she was cleaning out her closet. Specifically, she was tossing an old, stretched-out, long-sleeved white tee and feeling liberated. I read her message, then looked down. I was wearing an old, stretched-out, long-sleeved white tee and feeling frumpy.

This did not seem coincidental. I felt that nudge in my spirit, the loving shove that says, Let’s start letting some of these old things go, sweetie. It’s time.

So I asked Brooke questions about her decluttering process, and tried to open up to the idea of doing something similar. 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 or what’s for supper. And sure, those falling-apart yoga pants were pretty bad, but did it matter? Since I’m self-employed, there are days in which the only people I see are Jonathan, Bootsie the cat, and the people at our local library.

Change Your Clothes, Change Your Life

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

“Read into the gaps [in your wardrobe basics]. Have you gone through seventeen monsoon seasons without a good-looking raincoat or trench? …. What in your belief system allows you to operate without these basic wardrobe necessities? This can be easier to suss out in a less emotional environment like, say, a kitchen – you wouldn’t go three years without … a pot big enough to boil water, would you?

But we tend to bind up our identities in our clothes, so that instead of realizing we have a simple problem with a simple fix …. 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 how absurd it was. For practically my whole adult life, I’d beaten myself up for not dressing better, while simultaneously refusing to give up ratty clothes, much less buy nice ones. I’d pushed myself to obey contradictory internal commands: dress well, but don’t throw anything away or spend any money.

The Decluttering Process

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

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

I found it most difficult to let go of worn-out items that were gifts from beloved people. My mom gave me those yoga pants, and they’d been cute before I’d worn them every week for two years. My friend Rachel gave me that satin top, and it had made me feel glamorous before it discolored.

There was sadness in letting these 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. When I let them go, it made me feel like I could be trusted to lead my own life.

That’s the thing about decluttering: it’s a tactile truth-telling exercise. To me, cleaning my closet is not about being wasteful, spending lots of money, or becoming a fashion plate. Instead, it’s about practicing self-honesty.

The Power of Honesty

When I get real about which clothes look good, I can tap into that honesty in other areas of life. It’s transitive. Admitting that a shirt’s life is over somehow 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 out for a run in athletic clothes that aren’t rags, I am more likely to smile and be friendly. When I push myself to wear a fitted jacket instead of my pajama fleece, I feel better about walking into the world. Ever since I made the resolution to dress better, I’ve felt the weight of self-consciousness lifting.

But even if I don’t see anyone when I’m wearing nicer clothes, I’m starting to believe that feeling good about myself is reason enough.

As Liz Gilbert wrote so beautifully in Eat, Pray, Love, “ … I will leave [Italy] with the hope that the expansion of one person – the magnification of one life – is indeed an act of worth in this world. Even if that life, just this one time, happens to be nobody’s but my own.”

Daring to Dress Better

With that in mind, my current task is to (mindfully) acquire some new clothes. Unsurprisingly, I feel guilty about this, because part of me still believes that it’s wrong or selfish or frivolous to purchase clothes.

Spending is hard for me in general, but I also find certain types of purchases more stressful than others. I buy books and notebooks with relative ease, because I’m comfortable thinking of myself as a reader and a writer, a ‘brain’.

It’s harder to buy nice food and clothes, because I struggle with my status as an embodied human being with physical needs. When I do manage to buy fresh blueberries or leather boots, it’s a victory. It’s me honoring my body, and this real life I’ve been given.

Caroline McGraw, Jonathan McGraw

Me & my love (the cool guy), 2015

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

It would be nice to take this newfound energy on a shopping spree, but instead I’m rebuilding my wardrobe slowly and strategically. (Last month, I purchased one t-shirt, one purse, and one pair of shoes.) However, simply getting rid of the duds in my closet has made a huge difference in my life. Yes, I do laundry more often, but it’s worth it.

When I started wearing the nicer clothes I already had – when I dressed for each day as though I was a person of value – something shifted. I began to value myself. And that’s why I don’t mind telling people that my new year’s resolution is 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.


Have you cleaned out your closet lately? What’s your experience with daring to dress better?

Leave a comment, and be entered to win a new book! (See below for details.)

Update: Congratulations to Carolyn, the winner of the free copy!


Friends, thank you for warmly welcoming my friend and fellow writer Brooke Adams Law to this space last week! Your support and encouragement meant so much to both of us. Just a reminder that her newest digital book, Journeying Through Lent, is available on Amazon for $1.99.

Also, I wanted to let you know about another book I enjoyed recently: Andy Steiner’s How to Survive: The Extraordinary Resilience of Ordinary People (ThinkPiece Publishing, 2015).


The latest from ThinkPiece Publishing!

The Amazon summary notes, “Survival books tend to focus on the exotic, like a plane going down in the mountains. This one is for the rest of us. Andy Steiner explores resiliency in the face of such difficult life events as the death of a spouse, the loss of a child, the distress of bankruptcy, the trauma of a heart attack, and more.”

The ThinkPiece team published my latest Kindle Single, I Was a Stranger to Beauty – in fact, mine was the first book they ever published! – so I get to enjoy fun perks such as advance copies of books from fellow ThinkPiece authors.

And so I want to pay it forward. Leave a comment on this post, and you’ll be entered to win my print copy of How to Survive. I’ll select a winner by random drawing on Monday, March 16. Good luck to all!

23 thoughts on “In Which I Dare To … Dress Better.

  1. This post came at the perfect time for me! Working on this exact thing. I am always amazed at how your posts resonate even though our lives are not visibly similar. And thank you for mentioning How To Survive. I am reading a LOT in this vein lately but had not heard of this one. Would dearly love to win it. I am a widow trying to figure out How To Survive as a single mom, getting past the wreckage of the business my husband and I built together, and not getting past but integrating my continuing love for my husband despite his absence.

    • Carolyn, I’m so glad to hear that! I hesitated on publishing this post, because I was wondering whether or not the topic was too ‘small’, too insignificant to anyone else but me … so thank you for sharing that it hit home for you!

      And what beautiful words you wrote about what must be a very, very challenging time. I will make sure you get a copy of How To Survive, whether or not your number comes up in the randomized drawing. Thank you for being here! (hug)

  2. Laurie says:

    This was so thought provoking and true. It is perfectly acceptable to dress so that we feel comfortable!

  3. What a fascinating post, Caroline. I relate to so much of it. I’ve been in a process of clearing out closets and drawers off and on for about the past year, and it really has been more freeing than I’d anticipated to let go of things that no longer fit with who I am today. As you experienced, some of the hardest pieces of clothing to let go of were gifts from people close to me. So I get that. Thanks for inspiring me to do even more clearing out the old and bringing in what feels good! 🙂

    • Jill, you are very welcome! That means so much coming from you, as your work always galvanizes me to take better care of myself. As I mentioned in an earlier comment, I was nervous about whether or not this post would be of interest/relevance to anyone else, and I’m so thankful it spoke out to you!

  4. love this essay love that you said “I only kept clothes that made me feel joyful and confident” it was so long before i was able to feel good about my clothes. any clothes. it was gradual from the age 40 to 50 and now i love dressing and playing with my clothes. Working in a consignment shop owned by an artist who helped me find a style that made me feel good. just got this poem this morning… and if you do not believe in God .. just substitute the words “what’s important” or something that is important to you. and substitute for “savior” “that story about Jesus”

    I have a need
    of such a clearance
    as the Saviour effected in the temple of Jerusalem
    a riddance of the clutter
    of what is secondary
    that blocks the way
    to the all-important central emptiness
    which is filled
    with the presence of God alone.

    Jean Danielou
    Source: quoted in Lost in Wonder by Esther de Waal

  5. What an interesting post. You are so tall and willowy thin like a super model that I would’ve never guessed you were anything but a ‘Bond Girl.’ BTW, that coat in your photos is FABULOUS!

    About once or twice a year, I will go through and clear out my closet. I LOVE DOING THIS. As I make space inside my closet for new things, I feel my heart making room for new things as well.

    I’m glad you’re on the new path and appreciate your precious honesty.

    • Haha, now you know the truth! Inside I am always the girl in the pink glasses. 😉 Thank you, Marcy. And I agree – it is such a wonderful feeling to go through one’s closet and make room. Here’s to you and the new things you’ll welcome this year!

  6. Donna says:

    This really hit home! I have clothes in my closet that have been around for so many years. I have tops that my mom gave me that I struggle to get rid of since she has passed away! I know that I need to clear out my closet…why don’t/can’t I do it??!! Thanks for getting me thinking about this seriously.

    • You’re very welcome, Donna – I can definitely empathize with the challenge of letting go of clothes that were gifts from loved ones.

      One practice that has helped me (which I read about in Marie Kondo’s The Life-Changing Magic of Tidying Up), is to verbally thank the clothes for their service in your life as you let them go.

      For gifts, I also thank the giver aloud before letting the item go. Even though the givers can’t hear me, I like to think that they’ll receive the gratitude somehow. Best of luck with your clearing out!

  7. Renee says:

    Loved this post! I also have several favorite wardrobe items that I like to wear. For me, they’re comfortable and familiar old friends. I have gotten much better about parting with old clothes, although the ones that I am sentimentally attached to tend to stay until they are nearly falling apart before I will part with them.

    I am all over the place with regards to purchasing nice clothes for myself. Generally, I have no problem buying myself nice things every so often, but I do hit a sticking point when it comes time to wear them because I don’t feel that I am worth it, or I do not want to stick out and be noticed too much. I wear slacks to work so often that on the rare occasions I do wear a dress, everyone thinks I have a job interview. It’s crazy.

    So, I intentionally purchased a bright red Calvin Klein dress that happened to be on sale and I made myself wear it to work. Boy, did I get noticed! It looks spectacular on me and I feel like a million bucks when I wear it. It’s a feeling I want to experience more often, so I am slowly building up my wardrobe to include beautiful clothes that make me feel good. They don’t have to be designer clothes, either. If I feel good wearing them, that is all that is required.

    I have noticed how many people, including myself (although less and less often), dress in strictly dark clothes, and I wonder is it because dark colors are slimming, or because dark clothes help them to feel invisible and not stand out because they don’t think they are worth being noticed? Once I started noticing that, I made a conscious decision to wear brighter, more colorful tops with my work slacks. It lifted my mood immediately and I felt an energy change in my body, which usually translates to a more productive day.

    • Renee, I’m so glad that you enjoyed the post! And what a great story about the red dress – sounds like you made a splash! I can relate to that feeling of not wanting to be ‘seen’, and the next time I’m tempted to go invisible, I’ll think of you and choose some color instead. 🙂

  8. (I’m behind the times here–actually just read today’s post and then went backwards to this…which is PERFECT because I spent the whole day cleaning out my closet!)

    Clothes have always been a challenge for me: I was a born Tom boy–wanting to play football and hotbox (baseball) in the yard with Dad and my brothers. I was in my 40’s when I overheard the man I was dating refer to me as sexy. He later said “Why are you acting so dumb? That’s so not like you!” Subconsciously I believed that girls are either smart or pretty (not both) and was acting the part. In addition to this I still can’t walk in heels (so give me a nice chunky cowboy boot 🙂 As a musician, I let myself dress up to perform (and to be honest I love it!) Yet I find my daily wear (ware?) to be black pants and loose tops. And I can’t get rid of a dress that I bartered for in the market in Bangkok 20 years ago. (sigh).

    All this to say THANK YOU Caroline for a thought provoking, inspiring post. I know I’m not alone!

    • Mary, what a cool synchronicity! I’m glad to hear that the post resonated with you, and I appreciate you sharing from your experience. You make a good point that beliefs and identities influence our clothing choices, and vice versa.

      Like you, I’m going for comfort in my daily wear – I’ll pick boots over heels any day! 🙂 – so my challenge is to choose items of good quality that fit well, rather than cling to raggedy stuff. Congrats on the closet cleanout, and thank you again for the comment! (hug)

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