The Best Fashion "Mistake" I Ever Made


By Tess Holiday(As Told To Kelsey Miller) 


The other day I was browsing the dress section at a popular chain clothing store, when I noticed something strangely familiar. It was a red and white dress made of cheap but vibrant fabric, which could most generously be described as “sporty.” Another word I might use is, “hideous.” But honestly, who am I to judge? I recognized that dress immediately because, back in high school, I wore the exact same one.

That was back in my Spice Girls phase. I remember I wore the dress with two clips on either side of my head, and a necklace that said, “brat.” You could argue that virtually every adolescent girl who grew up in the 90s went through a similarly regrettable period, wearing shiny tracksuits, glittery platform sneakers, and dresses the color of stop signs. But my Spice Girls phase was particularly tricky. As a fat girl growing up in Mississippi, with neither the access to decent clothing nor the money to buy it, I had to make do with what I had.

If I had a fashion motto back then, that was it: Make do. While I would often spot looks or trends I liked, and sometimes made attempts to emulate them (hence, my so-called sporty dress), for the most part I just had to work with what I could find at the local mall. Correction: the two stores at the local mall which carried clothing in my size. Clothing wasn’t about self-expression so much as literally covering my body, and hopefully, not fitting too uncomfortably.

But even while I was totally out of step with my classmates, I still managed to make some of those classic teenaged missteps when it came to clothing. Somewhere, there is a yearbook photo of me, in which I appear to be wearing a t-shirt emblazoned with a giant photograph of feet.

Just let me explain.

At this point, I’d moved on from the Spice Girls and was obsessed with the Dixie Chicks. On picture day, I wore a shirt printed with a picture of the band members, all sitting together in one chair. However, in the photo, they were seated in such a way that their feet were up at the top of the photo, across my chest—precisely where the yearbook photo cut off at the bottom. So, in the picture, all you can see is my face with an enormous smile on it, and right below that, three pairs of feet.

Needless to say, the other kids made plenty of fun of me for that. But that was nothing new. Really, it was all I knew, and it never occurred to me that things might change—that my appearance might be anything but a subject of ridicule, that getting dressed might ever get easier, let alone fun. If you’d told that girl in the feet photo that one day she’d get dressed up and photographed for a living, she would have looked around and backed away slowly, assuming you were a total lunatic.

But, somehow, that is what happened. By my early twenties, I was living in Los Angeles and had begun working as a professional model. That’s when everything changed. Going to work, I’d see racks and racks of clothing: Dressy outfits, casual pieces, retro styles, business attire—all in my size! It seems crazy to say this now, but that was the first time I’d seen any variety in the clothing I could wear. It was the first time I’d had options. Trying on the different looks I wore at modeling gigs, my own true sense of style began to emerge. I learned what I liked—skirts, bodysuits, and especially dresses. I discovered the growing (still small, but growing) crop of plus-size designers and retailers out there, and I started to experiment and hone in my own, true style.

It wasn't an overnight change—it never is. But suddenly it was as if a door had been opened. This was the moment I walked through it: I was walking around East LA one day, wearing a strapless, leopard-print dress, and a cardigan. I always wore a cardigan. Even though I’d started trying on all sorts of new styles, I never left the house with my arms uncovered. That would have been simply unacceptable, I thought. I literally chose every piece of clothing based on which of my cardigans it might go with. But on this day, walking around under the blazing Los Angeles sun, I was...well, I was just really effing hot! It wasn’t sweater weather! So, for the first time, I took the cardigan off.

At first, I felt uncomfortable and exposed. While I could pose in front of the camera with a million eyes on me, I’d never just walked around my neighborhood with my arms showing. But, nervous as I was, I was also way more comfortable. And in that moment, it clicked. I thought, Forget it. I’m not going to walk around Southern California in a sweater for the rest of my life. Also, this dress is cute as hell, and I just want to be myself. Who cares what other people think?

You know what other people thought, by the way? NOTHING. No one cared. I walked around in a strapless dress and nobody even noticed. Obviously.

That was that. Shortly thereafter, I threw all my cardigans in the trash and never looked back. From that day forward, I quit carrying around the burden of what other people thought (or what I imagined they thought) about the way I dressed. I chose clothing I liked, clothing that fit me well, and clothing in which I felt comfortable, in every sense of the word.

If I feel good in it, that’s all that matters. That might mean a pair of denim shorts and a gingham top, when I’m out in the country with my family. It could be a sleek, floor-length evening gown, when I’m headed to a black-tie event. Some days, it’s basic black pants and the first t-shirt I can find in the drawer, because I’m a full-time working mom of two, and sometimes you’ve just gotta get dressed.

The point is, no matter what I’m wearing, I chose it. I dress for myself, my comfort, and my lifestyle. That’s the only priority. When I think back on that kid in Mississippi, who got dressed every day just trying to make do—despite the t-shirt mishaps and the tacky dresses—I ache for her. But I’m proud of her, too. She hung in there, and she kept trying. Because of her, I get to be me.