The Well Midlife

Dressing for Who I’m Becoming: A Midlife Style Shift

striped tank top and green blazer midlife style

A midlife style awakening, one striped pant at a time.

The Closet That Was Hiding Me

For years, my closet was a a walking apology. An all black uniform meant to hide my size and my age. I dressed to try to make my body look like the body I wished I had instead of the one I was living in, and I called it personal style.

The sad part is, I thought I had style. That style, however, consisted of nothing but black and baggy. Black leggings especially were the workhorse of my wardrobe. They were slimming, they were neutral, and they were comfortable. I wore them to work, to funerals, on date night. I even had a favorite brand, Soma, and I’d buy them in bulk every time I visited one of their shops. I remember once on vacation in Charleston I came across one, and was thrilled to be able to shop on vacation for once, even if it was just adding to my legging collection.

I was dressing for a version of me that was trying to disappear. Trying to be thinner. Trying to be age-appropriate, since society tells us we need to tone it down when we hit a certain decade.

The crazy part? I thought I was doing it right.

The Made Up Style Rules I Was Following

If you’d asked me back then, I would have told you I knew fashion. I knew what was flattering for my shape and what was acceptable for my age. I knew which colors made me look slimmer, which silhouettes hid my midsection, and which necklines drew the eye “up and away” from the parts of me I’d been taught were a problem.

I had absorbed every single rule:

I was a walking Pinterest board of “what not to wear when you’re overweight and over 40.” And I was miserable. I hated my closet. I hated getting dressed. I hated my body.

The Moment Something Changed

I can’t point to one specific day. It was more like a slow exhale, a quiet realization that I had been dressing to manage other people’s perception of my body for so long that I had completely lost what I liked.

The shift started on Instagram. I began following plus-size influencers and seeing real bodies with real stomachs, not airbrushed models in studio lighting. Women, like Bonnie Wyrick, with bodies that looked like mine, confidently wearing things I would never have dared to put on. Amanda Roe inspired me with her pooch-positive message and outfits. As I watched these ladies get dressed every day, something in me started to soften.

If they could wear it and look good, maybe I could too. They gave me permission.

So I started experimenting. I dared to wear a crop top one day. Then colors other than black. I started reaching for comfort over flattering instead of punishing my body for existing as it was. I picked up items in stores and asked myself things I hadn’t for years. Do I love this? Does this make me feel good?

When was the last time I had bought something because I loved it, instead of because it made me look smaller? I couldn’t remember.

That was over a year ago. The closet I have now would be unrecognizable to the woman standing in front of my old one. 

From Hiding My Body to Falling Back in Love With It

my favorite striped knit pants in orange

Here’s the thing nobody tells you about wearing baggy clothes to hide your body: it doesn’t make you feel better about your body. It just reinforces daily that your body is something to be hidden.

When I started giving myself permission to wear more form-fitting clothes that showed my shape, something shifted. I had to look at myself, really look. Slowly, I could look in the mirror without hating what stared back at me.

My journey to accepting my body didn’t immediately jump to loving it. It started with neutrality; not hating it. That was the bar, and clearing it felt like a small miracle.

Then neutrality grew into something else. I started noticing what parts of my body I liked. My back was quite nice. The curve of my collarbone might actually be sexy. I started showing those parts off instead of fixating on the parts I wanted to hide. The whole equation flipped. Instead of dressing to camouflage what I didn’t like, I started dressing to celebrate what I did.

It sounds crazy, but striped pants were my gateway drug. They were bold, in comparison to black leggings, although my first pair was a subdued khaki and white vertical striped wide leg pant. The first time I wore them out, I felt incredible. Not because anyone complimented me, though they did, but because for the first time in years, I had put on pants that felt like me. They were soft and comfortable, they draped beautifully and they didn’t squeeze the tummy. They were meant to be seen. I did what any one would do; I bought multiple pairs in different colors.

My body didn’t change. My relationship with it did, because the way I got dressed every morning did. Dressing like someone I cared about made me start to care about myself. Shocking.

Style Is Not a Reward for Leaving the House

For a long time, I treated “real” clothes as something I earned by having somewhere important to go. Errands, dog walks, working from home, hanging out with my husband, all of that got the same rotation of long shirts and black leggings. That was the bulk of my everyday life.

The clothes I loved (more accurately, the few I tolerated) sat in my closet waiting for an occasion that rarely came. I didn’t feel worthy of dressing well.

Somewhere along the way, I learned that comfortable and fashionable weren’t mutually exclusive. I could wear something I loved and be able to breathe in it. You couldn’t pay me to wear shapewear now. Maybe it started with the striped pants.

Now I get dressed to make me feel confident and ready to tackle the day, even if it’s for me and no one else. The grocery store gets the good outfit. The dog walk gets the good outfit. Your average Tuesday gets the good outfit.

I went through my closet and got rid of everything that didn’t fit, didn’t light me up, or was “appropriate and flattering” but not me. I donated all the tunic length shirts; it was no longer a requirement for a top to cover my butt in leggings. I realized black near my face wasn’t very flattering, so all my black tops went too. The “dressy” sweats I once saved for going out? Also donated. I did keep one pair of black leggings, but they’re shiny, sexy going out leggings to rock with knee high boots.

I was left with very little clothing, but I finally started wearing what was left. Even more fun was adding to my wardrobe with my new style rules (or lack of) in mind. 

The New Style Rules

I hate to call them rules, what I follow now is more of style guidelines.

That’s it. Clothes shopping and getting dressed in the morning is really that simple now. I wish I could go back and tell my old, all-black-leggings self what I know now.

“Flattering” is a trap. It’s a word that almost always means “makes you look thinner.” You are allowed to wear things that aren’t designed to shrink you.

Age-appropriate is a marketing concept. There is no expiration date on color, on print, on shape, on fun. You get to decide what you wear at every age you’re lucky enough to reach.

Stop picking stick-thin models as your style icons. Pick someone with a realistic body similar to yours whose style you admire. Looking at women who shared my size and shape changed everything about how I shop.

Your body is not the problem your clothes are trying to solve. Clothes are supposed to be a tool for self-expression, not damage control.

Confidence isn’t something you have before you get dressed. It’s something that builds because of how you get dressed. Wearing what you love teaches you to trust yourself in other places, too.

The Closet I Have Now

These days, my closet looks nothing like it used to. There’s color. There’s print. There are pieces that hug, pieces that flow, pieces that break every rule I used to live by. I own ten pairs of striped pants from forest green to chocolate brown; they’re proof of how far I’ve come.

There are still plenty of neutrals in there, but they’re stylish. They’re the kind of pieces that make it easy to throw together a matching outfit and add a pop of color or print without thinking too hard. I rarely wear black anymore. It’s amazing how much more alive I look when I’m not draped in something designed to make me fade into the background.

Everything in there now is something I chose, not something I settled for because it was “safe.” The barrel leg sweats that make sweatpants fashionable, the boxy tee I swore I couldn’t pull off now hanging in my closet in six colors, and the pastel asymmetrical shawls I wear with everything from satin slip shorts to wide leg pants. None of them are safe, but all of them are me.

I’m no longer dressing for the woman I was, the one trying to disappear, to be appropriate, to take up less space. I’m dressing for the woman I’m becoming, the one who walks into a room in stripes or a crop top confidently. I give myself the time every morning to put together an outfit that matches my mood, even if I’m only working from home. Especially if I’m only working from home.

Even my hubby, Mike, got pulled into the style upgrade. We were walking into the bookstore one day when he looked over and said, almost surprised, “You look really cute today. Actually, you look really cute all the time now.” It was a compliment, but you could hear the wheels turning. Suddenly his rotation of graphic tees, hoodies, and cargo shorts didn’t feel as appealing as it used to. He was tired of us looking like Justin and Hailey Bieber, always dressed like we were heading to two completely different occasions. A few weeks later, he asked if I’d help him upgrade his wardrobe. I was thrilled.

If You’re Standing in Front of Your Closet Right Now

Consider this your invitation to dress for yourself, your permission slip to wear whatever the hell makes you feel good. They say to dress for the job you want. I say dress for the woman you want to be. Start with one question: What would I wear today if I didn’t care what anyone else thought? Then go put it on. The woman you’re becoming has been waiting.

If this resonated, I’d love to hear from you. Tell me what arbitrary rule you’re tired of following.