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Not-So-Skinny Jeans: How Going Up a Pant Size Increased My Self-Confidence

Is your self-confidence at an all time low? Here's my best encouragment on how to stop being your own worst critc & give yourself more grace.
I'm Stephanie May Wilson!

I'm an author and podcaster and my specialty is helping women navigate big decisions, life transitions — creating lives they love.

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I’m not sure how it happened exactly. It didn’t happen overnight, or even quickly, and I certainly didn’t realize it. But somehow in the 6 or so months after my husband and I got married, I got BIGGER.

Maybe it was the date nights, or the fact that he was teaching me how to cook. Maybe it’s that I stopped worrying about it. My wedding dress had fit, the photos were taken, done and done. Maybe it was the fact that I couldn’t peel myself out of bed in the morning — couldn’t bring myself to trade in the world’s greatest cuddler for a treadmill. Or maybe it was all the life transition we were going through — newlyweds in a new city with new jobs. New everything!

Whatever it was (likely a combination of all of the above), I woke up a few months into our marriage feeling lumpy, miserable, and mad.

I started noticing sometime around the fall. When I finally traded my shorts and sundresses for skinny jeans, I realized I wasn’t quite so skinny anymore. They didn’t fit like the glove they used to be. Instead they were miserable to wiggle into. They took a fight to get up and over my hips, and an army to close. And once I was finally in them (which was still possible, although barely), I began counting the minutes until I could take them off again.

I felt gross. I felt uncomfortable. But worst of all, I was furious with myself.

“How could you have let this happen?” I berated myself. I’d glare at my fleshy body every time it had the nerve to pass a mirror.

I think I thought that if I was mean enough to myself about it, or angry enough, or disgusted enough, that something in that would make me change.

Have you ever thought that?

I catch myself doing this with lots of things — trying to motivate myself through fear, or intimidation, or by being just plain mean.

I think I’ve always figured that if I was my toughest critic, nobody could be tougher on me. I found comfort in that somehow, although I’m not sure exactly how.

So I continued to wear my skinny jeans. I continued to force myself to put them on, and tried to squeeze myself into healthy submission.

“You have to eat a salad today. Have you seen yourself!?” I’d ask myself with distain. And when I’d inevitably fall off the wagon and order a cheeseburger, my inner critic was relentless.

Life went on like this for months until I’d finally just had enough.

“I desperately need some grace,” I found myself thinking one day. And so against everything I'd done before, that’s exactly what I decided to give myself.

My mom and I were going shopping a few days later and I made it my mission to buy the softest things I could find. Soft, flowy tanks, and loose fitting shirts, oversized sweaters that made me feel small and tucked in, cozy instead of squeezed.

For the first time I shopped like I loved myself, like I wanted to do something nice for myself, instead of punishing myself until my body got its act together.

And then I arrived in the jean section.

I wavered. I’ve always been the same jean size. Buying a size up felt like admitting defeat. If I bought a bigger size, what would ever make me lose weight? I reasoned.

But then I remembered grace. I remembered how those squeezy, awful jeans made me feel, and I remembered that I had decided to love myself. So I marched straight in and asked for the next size up.

The saleswoman knocked on my dressing room door and handed me a pair of jeans. “They’re the size you asked for,” she said. “They’re high-rise and they’re stretchy. I think you’ll love them.”

They felt like butter in my hands.

Slipping them on was one of the best feelings I’d ever felt. It was like slipping down between cool sheets at the end of a long day, or taking a shower for the first time after a long camping trip. They felt delicious. They were soft and forgiving and buttoned perfectly up over my hips, hemming me in just enough but not too much.

I could move in them, breathe in them, be in them without counting the seconds until I could take them off again. Best of all I felt beautiful in them. In them, and with grace wrapped around my slightly bigger body, I felt like maybe, just maybe, I was okay after all.

The thing is, we’re not perfect. Sometimes life happens and we end up in situations that we never intended.

We make a mistake, or lose our way, or get distracted for a bit too long and end up lost. We find ourselves being someone we never intended to be, or acting as though we’re someone who we’re really not. We find ourselves looking different, being different, or doing something that’s disappointing to us if we’re honest with ourselves.

And in response, it’s easy to berate ourselves. It’s easy to become our own worst critic, shoving ourselves back into line as though that will help.

But what I learned this winter is that we really don’t need someone in our head hating us. We don’t need to be berated or shown again and again all that we’ve done wrong.

It doesn’t make us hustle faster to be mean to ourselves, and it didn’t make me lose the weight faster to punish myself for putting it on in the first place.

What we really need is grace.

A few months later, I was getting ready for work. I grabbed my favorite jeans about to slip them on when I realized all that had changed in the last few months. I’d been able to get dressed for work without feeling awful about myself. I’d been able to concentrate while sitting at my desk because I didn’t have denim squeezing my middle too tight. I felt comfortable in my own skin for the first time in a long time, and much to my amazement, I’d even shed a few pounds.

“Thank you Jesus,” I began to pray. “Thank you for loving me, and accepting me, and giving me heaping amounts of grace…”

And just as I said that, I looked down at the pair of jeans in my hand. Stitched into the label was a word, plain as day, that I’d never noticed before.


If you need more encouragement in this area, here are a few resources you might like:

Girls Night #71: How to Overcome Insecurity and Embrace Your Identity in Christ

Girls Night #2: I'm not in the Shape I Want to be in, I Don't Feel Confident in my Skin — How do I Change That?

Girls Night #99: How to Have True Confidence as a Christian Woman

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Is your self-confidence at an all time low? Here's my best encouragment on how to stop being your own worst critc & give yourself more grace.

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  1. KourtneY says:

    You have a very hateful IMG (Inner Mean Girl) it’s the person who always tells me I’m to fat to run that half marathon or I’m never going to have a successful career because I have had to start over to many times. Sometimes we just have to tell our IMG to sit down and shut up. Don’t let her get to you! We are all capable of so many wonderful things!

  2. Toni-Lyn says:

    I love this! I think this is something that happens often. Instead of focusing on how happy we are (which may or may not have been what got us into the bigger sizes in the first place) we focus on self-loathing. I found myself in a similar place after dating my guy for a few months. He’s a great cook and he seems to specialize in dishes with sausage and bacon where I am pretty strictly a chicken, soups, and pasta gal. I didn’t want him to stop cooking for me or have his feelings hurt so I didn’t say anything for awhile. It’s been about 19 mos. we’ve been together and I’m really just in the last two months kind of getting back on track exercise-wise. But physical health isn’t complete without mental health. The only thing worse than trying on pants is trying on shorts, and both have ruined my day many-a-time! Thanks for sharing!

  3. I love this, Steph. I’ve been on a similar journey, though more because I’ve been a bigger size for longer than I would’ve liked. I’ve got a post in the works about the realization I had that changed it all — my body is not an enemy to be fought with.

    And you’re just as lovely as ever. Bigger pant size and all. 🙂

  4. Jess Rice says:


    Your words never cease speaking to me, it’s like we live in the same brain wave at all times hahah. I miss you dearly and things like this are why we must have facetime dates hahah I can’t even tell you how true this is to me, how encouraging it is just to hear that someone else is with me in this crazy chaotic first year of marriage, moving, transition and change and I’m so thankful it’s you!

    Love you!

  5. I needed this, Stephanie! The enemy constantly tells me I’m not good enough, pretty enough for my boyfriend, or skinny enough. What I need to do is to give myself grace when my body isn’t supermodel-worthy. Thank you for this!

  6. Ashlin horne says:

    I love this post so much!! Well done.

  7. You have so beautifully and articulately described a struggle that is so common for many, myself included. The way you brought light to the fact the often we are our own worst critic resonated deeply. In my own journey to live in grace, especially in the realm of eating and body image, I’ve begun shifting my view of food as either being ‘good’ or ‘bad’ and instead focusing on how what I am eating is nourishing and caring for my body. Thanks your honestly!

  8. Beth says:

    Thank you! Thank you! These are the exact thoughts I’ve been having about myself for the past 6-12 months. I’m getting older and I’m gaining weight, but feeling healthier than ever. I’m realizing I need to stop hating myself for the weight and just roll with it. Find clothes that I feel comfortable and beautiful in. Thank you for the kind words. I want to love my body – no matter what size I’m wearing.

  9. Ariel says:

    You have no clue how much this post means to me! I’m a new mom and have been going through a lot of transitions. I had pre baby clothes that I no longer fit and it has been the worst feeling ever. I force myself into clothes that don’t fit! I’ve been uncomfortable at my desk because my pants are too tight. I’ve been there and so reading this I think is Gods way of telling me to give myself grace! I haven’t been liking how I looked lately and this was a huge wake up call to that. I’ve never been like that so this has been super hard. Thank you for sharing and being honest because it has opened my eyes. I will definitely be going shopping for a new pair of jeans a size up! Thanks

  10. […] wearing all along! And in case you’re looking for some additional reading, I remember reading this article from my blog-buddy Stephanie that is totally worth the […]

  11. Kristin says:

    This is a powerful message.
    I think we need to know what kind of jeans you bought that made you feel so good about yourself (and the whole butter in the hands thing 🙂

    • Stephanie May Wilson says:

      Thank you so much for reading Kristin! And oh my gosh, I wish I remembered what brand they were! I ended up losing them! (can you believe it?!) If I figure it out though, I’ll for sure let you know! 🙂

  12. Mercedes says:

    This hit me hard. I’ve always told myself that I have to lose the weight and that I have to push myself, but never told myself to love who I am and who God made me. I wasn’t loving myself. The harder I was on myself, the Unhealthier I was. Thank you for being a light. Thank you for speaking truth. Thank you for reminding me I need grace first.

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