My parents rolled into town last week with a huge emotional bomb in their back seat: three huge boxes full of mementos, photos, notes, and memorabilia from the past two decades. As I opened each envelope, I couldn’t look away, even though I desperately wanted to. It was like being visited by a ghost, and also like looking at yourself outside of your body.

I remember having these photos taken. I remember passing the notes. I remember the thoughts inside my head. And now, I am so far removed from who these past versions of myself were that I am able to push my judgment of them aside just enough for a little empathy to slide in—for what I was going through and who I was—thanks to the benefit of hindsight. 

Our Wit & Delight September theme is on the topic of reinvention. So come, take a little tour with me, of how I reinvented myself through the years, over and over again, to become the person I am today.

Middle School

Is there a harder time in life than middle school? I remember looking at my friends and thinking, HOW do they know how to do this? How do they know how to talk to boys? How do they know what to wear? How to be cool and not awkward all the time? I was sweaty and nervous and second-guessed myself constantly.

It was like watching a chameleon change color, trying on different personas that didn’t quite fit.

When I went through pictures from middle school, I found snaps my friend and I had taken of each other in different outfits (as pictured on the right). It was like watching a chameleon change color, trying on different personas that didn’t quite fit. Even now when I meet a middle schooler, I feel that twinge of insecurity that arose in the years between girlhood and womanhood, when I’m sure many of us realized growing up was going to make life a lot more complicated. 

High School

Ah, braces in high school. What a way to start the sophomore year!

I’d been freshly dumped for a girl my ex was starring in a musical with and felt that looking as close to Audrey Hepburn at homecoming would get him crawling back. Ah, to remember the first time we dressed for revenge. It worked, but I can’t say I was better off for any of it.

I remember these days as ones where I was slowly feeling more confident in my own skin. I decided to quit Irish dancing so I could spend more time being a kid, going to football games, and driving around with girlfriends before going off to college. After years logging 20+ hours a week practicing a craft I knew I wouldn’t take with me into adulthood, that decision probably marked the first time I advocated for what I needed, not what others wanted me to do.

When I see photos of myself in high school, I remember how badly I wanted to grow up, and how exciting it was to finally begin to develop a sense of confidence in who I was becoming. It would take years to foster, but at thirty-six, I can finally look back at this girl with some grace and understanding. 

When I see photos of myself in high school, I remember how badly I wanted to grow up, and how exciting it was to finally begin to develop a sense of confidence in who I was becoming. It would take years to foster, but at thirty-six, I can finally look back at this girl with some grace and understanding. 

College

There was nothing I didn’t love about college. The freedom was intoxicating. I found my passion for design and absolutely flourished in a sorority full of friends I would have never found had we not all been shoved together by a very strange and archaic system.

Underneath the surface, issues with food and controlling my eating habits were present and when I look at these photos, I feel both nostalgic and tender about what I was going through. I hadn’t found enough confidence in my ideas or thoughts to not try to make up for them by fitting into a size zero or carrying designer bags I couldn’t afford. I truly believed that hard work and grit was the secret sauce to achieving the armor of perfection. Little did I know a whole world of hurt was waiting for me after graduation. 

I truly believed that hard work and grit was the secret sauce to achieving the armor of perfection. Little did I know a whole world of hurt was waiting for me after graduation. 

Early Twenties

Bootleggers, is that you?

I know only a few Twin Cities folks in their early – late thirties will truly understand that reference, but if you are one of them, I’m sure you have memories on that dance floor making moves to Timberland and Nelly Furtado. There were a lot of arm parties, a lot of very thick belts, a lot of back-brushed hair poofs, and zero responsibility. YOLO, work hard play hard—I was living the stereotype on borrowed time.

They were the twilight years of my college days, and it was following these years that divorce and therapy came to crash the party. Life looked a lot different on the other side, like the lights got turned on at 2:00 a.m. at the bar.

December 2011

I snapped this photo on the back of the six bus. I sold my car and used public transportation to get everywhere. It was before Uber and Lyft and the on-demand economy. My divorce was finalized this month and little did I know, the real work was about to begin.

My divorce was finalized this month and little did I know, the real work was about to begin. . . . I did a lot of crying, and in a way, it was the most authentically in my own skin I’d felt in my twenty-eight years on Earth. 

I spent much of my time alone this year, with the support of my girlfriends and a budding new relationship that we both knew would be a failure to launch. I did a lot of crying, and in a way, it was the most authentically in my own skin I’d felt in my twenty-eight years on Earth. 

2012

I spent this entire summer on a plane. It was the first time W&D really felt like it was taking off. I was starting to make some money from the site and our readership was rising steadily. Pinterest was exploding and Instagram became the platform to watch. So naturally, OOTD, as pictured here.

It was also the summer I asked to get tested for ADHD. I missed more than one flight due to misreading my calendar and routinely failed to show up for therapy. 

2013

I met Joe in 2013. I can still remember what I was wearing the first time we locked eyes, and in many ways, the fundamental pieces of that outfit are still in rotation today: oversized Oxford blazers, men’s sweaters, loafers, and jeans.

We got married nine months later, me in the only wedding dress I tried on for the occasion. To me, seven years later, it still stands the test of time. 

2015

It’s 2015 and I’m on a plane every week. I have my packing routine down to a science and my uniform is sleek but adaptable. I’m feeling a bit puffy from salty room service food and cheap airline wine. Responsibilities are still slim but I have a grown-up job—consulting while working on W&D on the side. 

I wear almost the same thing every day, changing up the styling slightly here and there. I live in black, gray, and white. Turtlenecks become my go-to for everything and I feel lost without them in the summer. I buy more coats than I know what to do with. Almost everything I purchased I can no longer afford (kids, man!) but I still own almost every quality piece I invested in, from cashmere sweaters to Chanel flats. I’ve gotten smarter about replacing them now, shopping secondhand. This was a year I felt like I found my groove, and my “me” style. 

July 2017

Motherhood, year one. Stretchy fabrics. Forgiving thoughts. An expanding waistline. A second pregnancy only eight months postpartum with my first. I feel like my body isn’t my own and have little to no pictures of myself below my neck. A shame, now that I look back wondering what I was wearing because I have no memory of it. 

December 2017

Surprise baby, surprise birth. I was in the thick of the newborn phase and remember taking these photos because it was the first time I felt like I put together an outfit in over a year. Long layers hid my hair loss. Layers covered up the rolls I was coming to accept. Lipstick always helped. So did a good attitude, even when I was feeling hopeless. Acting like you’re OK can sometimes be as convincing as the real deal, especially when you’re in survival mode. 

Long layers hid my hair loss. Layers covered up the rolls I was coming to accept. Lipstick always helped. So did a good attitude, even when I was feeling hopeless. Acting like you’re OK can sometimes be as convincing as the real deal, especially when you’re in survival mode. 

May 2019

I get my spark back just as I sense a big change coming. I feel ready to quit W&D altogether and start something new. I stay, because I feel I still have something to say. I follow a voice that tells me to make small changes, a little at a time.

I move more, I eat a little less. I sleep, for the first time in two years, longer than in four-hour increments. I start shopping again, going back to the me who felt comfortable and confident in quality basics and classic styles. I start to style my hair again. I get a dermatologist. I begin to use face masks. I carve out time for me. I begin to look at getting dressed not as a chore but as something I get to do to express myself. I get dressed for me, as a way to put on a brave face when my future feels a bit shaky, because it’s something I can control, even when the winds of change might threaten to blow me in a new direction. 

2020

2020. The year of dressing as a form of survival, and an act of self-preservation. Snapping photos in a different outfit—or “fit” as we’ve come to call it—is a way to simply mark the differences between this day and the next.

In any other year, under any other circumstances, I don’t know that I’d find the pleasure in dressing just for me. It feels like a secret slice of happiness, knowing I’m capable of delight that requires no audience.

By summer, I feel the permission to throw whatever self-proclaimed rules of “you can’t wear that” out the window. I begin to accept the scar on my stomach won’t be budging when subjected to an unforgiving bikini line, and that the flap of skin where my kids once sat will be with me forever unless I’m willing to subject myself to the knife. It feels less dire a situation, like I could take it or leave it one way or another.

In any other year, under any other circumstances, I don’t know that I’d find the pleasure in dressing just for me. It feels like a secret slice of happiness, knowing I’m capable of delight that requires no audience. And that’s a style tip only those who keep on evolving can master. 

Kate Arends

Kate is the founder of Wit & Delight. She is currently learning how to play tennis and is forever testing the boundaries of her creative muscle. Follow her on Instagram at @witanddelight_.