Guest Post: My Love-Hate Relationship with Feeling Pretty

Feeling happy is probably my number two goal in life. (Number one, you’ll recall, is empowering women!) I’ve struggled with anxiety for over a decade, and as such I find it fairly difficult to feel happy. But I strive for it, mull it, try to find ways to grab little bits of happiness whenever and wherever I can. And I do my best to remind all of you lovely readers that looking great is only important insofar as it makes you feel great. That serenity, confidence, and happiness are the real endgame here.

So when Britt Reints contacted me about her new book, An Amateur’s Guide to the Pursuit of Happiness, I had to bite. I’ve read scientific studies and therapist-penned tomes about happiness, but I feel like the concept is so personal and ephemeral that clinical expertise has somewhat limited utility. Britt’s voice is honest, friendly, kind, and welcoming as she unfurls her own story and encourages you to start drafting your own. Today, she’s generously offered to share her own style and body image journey with us.

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moving on

Fashion and beauty had always been important to me. As a kid, I sketched pictures of dresses and dreamed of being a fashion designer. I convinced my mother to let me wear makeup in sixth grade by explaining that I wasn’t too young to feel attractive. My personal style was a significant part of my personal identity as an adult, too. It thrilled me when my mother referred to me as a fashionista or my friends called me for shopping advice. Once upon a time, I even had a shopping blog.

And then I got rid of all my shoes and all but my most functional clothes. At the time, I saw my shoe-shedding as proof of personal growth. I no longer needed a pair of red heels to make me feel bold, strong, or beautiful. I was better than that.

The decision to let go of my wardrobe was also a practical one: my family and I were moving into a 24-foot travel trailer and driving around the country for a year. I didn’t have room to be stylish, and I was certain our adventure was a much more enlightened pursuit.

Within a couple of weeks of moving into the RV, I stopped wearing makeup. What was the point when the only people who would see me were my husband, my kids and a bunch of strangers in a campground? A few months later, I decided to chop off my long, curly hair; I was going to save so much time and money. I told everyone it was “just hair” and I had better things to invest myself in.

And then we stopped traveling and eased back into normal life.

I went shopping with my beautiful friend Courtney and was struck by how lost I felt standing next to her in the mall. It wasn’t so much that I felt unattractive as I felt muddled and unsure of myself. I cringed every time we passed a mirror. I was featureless and shapeless with no makeup or accessories. I missed my beautiful hair.

I tried not to think about it.

I told myself that vanity was a sign of screwed-up priorities.

The truth was more complicated. I missed using fashion as a form of self-expression. I missed the beauty I would create and then get to enjoy in the mirror. I missed feeling beautiful.

It’s not that I spent my days feeling ugly or unattractive. Mostly, I just didn’t think about how I looked. But when I did, I was overwhelmed with conflicting emotions about how I should feel and how I did feel. I wasn’t certain that I wanted to throw myself back into creating a beautiful exterior, but I also felt like I’d lost something in my obsession with practicality, utility, and sparseness.

I decided to spend some time being honest with myself. What did I want? What was I really feeling and thinking – and what was I telling myself I should be feeling?

I had to admit that I wanted to play dress up once in a while. I wanted to feel beautiful without makeup, but I also wanted to remember how to use makeup to enhance my natural features.

I wasn’t entirely sure where to start. It had been so long and I had gotten so far away from my comfort zone, I felt like a complete style newbie. I turned to the Internet for advice and paid for a professional color analysis. I began restocking my closet with items that were in my palette and was delighted when my husband and kids started to notice.

“That looks good on you; that must be in your palette!” my husband says.

Now, I buy something new for myself about once a month, but it’s almost always from a thrift store – and in my personal color palette. My shoe collection is growing, but manageable. I do wear makeup for most occasions, but I’m also not afraid to run to the store or have coffee with a friend completely product free.

Living without a focus on external beauty helped me to break the connection between image and self worth. My weight doesn’t impact my mood and the clarity of my skin is not a measure of my value as a person. I am grateful for this separation of soul and surface.

But I’m also grateful for my beautiful curls and my sparkling blue eyes. I’m grateful for purples, blues, and pinks that make my skin radiant, and I’m thrilled for what the right shoe can do for my butt.

After spending some time at both extremes, I feel like I’ve finally settled at a comfortable middle place where I can embrace both my inner and outer beauty. And I’m no longer afraid to feel pretty.

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Britt Reints is the author of An Amateur’s Guide to the Pursuit of HappinessSign up for free weekly happiness challenges on her blog, or connect with her on Facebook.

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20 Responses to “Guest Post: My Love-Hate Relationship with Feeling Pretty”

  1. Cynthia

    First, I’d die for those curls of yours! My wife has curls like that and I’m so jealous – I swear in my next life, I get to be curly without paying for it 🙂

    Thanks very much for sharing your story – I can empathize, having drifted into a similar place when my three kids were very small, and having a similar bounce-back – and I really enjoyed your writing style, so excuse me while I go find your blog…

  2. Susan In Boston

    Britt, I think it’s useful for all of us to take this same “vacation” from dressing for the world. Sometimes it’s a choice, and sometimes it’s not, but it is always a discovery. You may look like hell for awhile (or at least feel that you do compared to what you did before), and how you and the world react to it is instructive. It sounds like you’ve found some important things.

    You might take another one at some point. I’ve taken three or four, and each time, I come back with less stuff but more insight and compassion. I’ve been on one for the last 5 years. It’s easier when you are older because you become invisible to the world anyway but you know who you are. I’m starting to get interested in sartorial play again, and the turning point was a spontaneous hair cut.

  3. Emily McIntyre

    I resonated with this post, Britt and Sally. Last year, 30 pounds heavier after a baby, I also cut off my hair (fingertip length to short-short) and traveled around the country in very few clothes. It was freeing, to a certain degree. But I missed the self-expression of dressing myself as I wished, and am still on the resultant journey.

    We travel so much, and have lived such an ambulatory life since then, that I’ve not rooted into myself well. This–learning the dance with weight, fitness, and self-expression–is a current challenge for me. Thanks for sharing yours!


    • Britt Reints

      I had a hard time feeling rooted when our physical location changed constantly also. It definitely adds to an already challenging process!

  4. Lynne

    Britt, your post really resonated with me. Living in a hospital for the last two months and in a way, letting go of my vanity (or pursuit thereof :), has actually led to more self-confidence. I did cut off most of my hair (and am planning to cut more off soon), but discovered I love the ease of care and the resurgence of my love for threader earrings. A simple foundation change to Bare Minerals has done wonders for my adult acne challenged skin, and cut down my beauty routine to a knock-off of Carmindy’s “Five Minute Face.” Except mine is three!

    I do have a wardrobe full of thrifted career wear, but am returning to college and changing careers. I find I’m simply wearing the old wardrobe in much more adventurous ways, even if they’re designed to withstand a cold environment right now. I feel simpler, yet more beautiful and more me than I have in years.

  5. Aya

    Thank you for this piece, Britt and Sally!

    The more I read about the experiences of other women, beauty, and self-esteem, the more I appreciate the different experiences and the common pressures women feel to look a certain way. (I was raised in a house of men, so I still feel new to all of this!)

    Thank you for this perspective; I find it has changed my conversations with other women about things like self-image and societal pressures.

  6. Anamarie

    I just had my hair colored for the first time, and it is not at all the color I had in mind. It has been three days now, and I still feel ugly. I otherwise have curly hair, and definitely consider my hair to be my best feature. I am so insecure/unhappy about the color that I think people are mocking me when they say it looks nice. I have to get it fixed so I can feel like myself again. 🙁

    • LIz

      It’s awful when that happens. I had a similar experience when a new colorist made my hair so dark it looked like I was going Goth.
      If you haven’t done so already, please contact the salon immediately and tell them you aren’t happy with your color and why. It helps to think about exactly what it is that seems wrong to you so you can tell them in detail, and tell them what you had in mind originally.
      Any good salon will try to remedy the problem and might not even charge you for the fix.

    • Anamarie

      Thanks, Liz and Britt. I can’t go back to same person for color. She will continue to cut my hair, but I can’t trust that she understands or sees what I see. I did tell her I was unhappy with it immediately “My hair is red!” And I asked her to bring back the swatch she showed me. She insisted it was just a little lighter. Think of a piece of dark chocolate next to an old penny. That’s the color difference! She told me to come back this week and she’d make it darker. I think her talents are in cutting, and I should have gone with my gut to go to a dedicated colorist! Appointment next Tuesday!

      • Eleanor's Trousers

        I color my own hair (for budget reasons) but I’ve had a few horrible experiments. Good luck with the new colorist! If you just want to strip the current color back to your natural hair, they sell a product called Color Oops in drugstores. It’s bleach/ ammonia free and I tried it last time I had accidentally purple hair. I’ve been dyeing for 15 years and it rinsed me back to my natural color (which I had no idea still existed) without drying my curly hair out. They should pay me to advertise for them- I’m like a Color Oops evangelist. That stuff is magic.

  7. Jean

    Much of what you said, Britt, resonates with me as well. I can’t understand those who say they don’t shop (though I only thrift shop) or don’t care what they wear, because, to me, fashion is fun self expression. And I really actually don’t care what others think of what I wear. But makeup is another story …. I could never not have the option of going makeup free or of wearing makeup. Likewise, I’ll never truly know how to wear it or put on a lot of it. So I consider myself in the middle. Thank you for this essay. I love your hair too, and identify with you and a poster above, that without my blonde-blonde straight hair and bold glasses I wouldn’t feel like myself.

  8. bubu

    It occurs to me that this is an issue that presents struggles for American women in particular – we have such conflicting messages and feelings about beauty, consumerism, intelligence, elitism, perception and self worth. I am always struck that French women seem to see no disconnect between being smart and pretty, taking care in one’s physical presentation without being perceived (by oneself or others) as vain or shallow. When I start to get tied up in these kinds of knots, I try to channel a little inner-French women — enjoy dressing with care, putting on the scarf and make-up, taking care of my health and beauty, but then going to embrace my intellectual pursuits with equal enjoyment and lack of self-consciousness.

  9. Carly

    Britt. one thing that I do from time to time that makes me feel pretty with no makeup is dye my own brows and lashes. For a small fortune you can also pay a professional to do this for you, but I diy it with supplies I buy on Amazon. As a blonde, this makes a huge impact for me and makes me feel like I have “makeup” on even when I don’t. Since you posted about Sally’s book in a Facebook status several weeks ago, I have been super curious about it as I seem to be in a similar place. I am ready to have a personal style. I’ve been floundering with it for years. This color palette thing? Never heard of it. How do you go about getting one done?