I Can’t Pull Everything Off, and That’s Okay

A stylist friend once told me that all you have to do to pull something off is put it on. If you’re worried about donning a particularly bold item, she said – gigantic fabric earrings, a complicated Rianna + Nina offering, anything owned by Cher— and carrying it off with confident aplomb, all you have to do is wear it. Once it’s on your body, you are pulling it off.

This is a beautiful sentiment. I support any aphorism that encourages people to experiment with whatever entices them (even if that thing is not technically an item of clothing), but with my friend’s absolutist approach, I have to disagree. It fails to take into account several important factors, one of which is me — more specifically, me at the Tibetan Freedom Concert in 1998.

I was a high school junior at my first music festival. Not even the sight of grown men chugging whiskey at 10 a.m. could diminish my thrill of standing in line to enter what I believed was an important cultural event. Somewhat less thrilling was the unseasonably humid weather, which was quickly creating a heat vortex on the unshaded parking-lot-cum-concessions-promenade outside Robert F. Kennedy stadium, which, by noon, was hot as a frying pan and teeming with bodies.

Drew Barrymore
(Photo by Mirek Towski/DMI/The LIFE Picture Collection/Getty Images)

As my friends and I pushed through the damp crowd, I caught sight of a row of small tables set up beside racks of crochet tops, sundresses and long flowy skirts. Behind each one sat a girl in her early 20s who looked like she inspired a folk ballad played on acoustic guitar (or shortly would). These were flower-tucked-behind-the-ear girls. Single-streak-of-Kool-Aid-red-hair girls. Vintage-camisoles-with-bra-straps-showing-and-floral-skirts-that-don’t-match-the-top-and-Doc-Martens girls. They were Drew Barrymore in Mad Love or Lisa Bonet in anything — the quintessential ’90s cool girl.

I was smitten. In the formative process of discovering what allegiances I held and what stuff I thought was bullshit, I’d recently pinpointed my target aesthetic as a combination of chic and bohemian. Unfortunately, as a kid in the suburbs in 1998, I had to attempt that vision using what I could find at the mall, which meant I rarely succeeded in looking anything other than “basic plus scarf.” To the Tibetan Freedom Concert, I wore boot-cut jeans, Steve Madden Chelsea-style boots and a black knit J. Crew shell. Yes, the outfit was boring, but the more pressing issue was that it was denim and wool and exceedingly hot.

As I stood in that sweltering stew of humanity, I gazed at the row of grunge muses. Unfazed by the cloying heat, they looked fresh and cool, as if they’d recently been unloaded from a meat locker. They also looked resoundingly themselves in a way I was desperate to emulate. Slowly, an idea floated to the mushy surface of my brain: Maybe all I had to do was to buy one of those long, crinkly floral dresses to become that girl. Maybe all that stood between me and my bohemian chic identity was one simple purchase.

Sweaty and possessed, I pushed past my friends, staggered toward the rack, pressed $20 into the hands of a girl with an inner wrist tattoo and barreled off to find the bathroom, new dress in hand. Alone in a stall, I peeled off my clothes, slipped the dress on and prepared for a transformation. Cool and nonbinding, it felt like wearing an April breeze, but I couldn’t put my finger on what felt so fundamentally wrong — that is, until I swung open the stall door and found myself face-to-face with a full-length mirror.

The eyes, shoulders, teeth and limbs I saw in the mirror all registered as my own, but taken as a whole, I was unrecognizable to myself. I would become acquainted with the concept of imposter syndrome a few years later, but I can confidently say that no needling insecurity has since suffused me with it as deeply as that $20 dress purchased in a sports arena parking lot. I had the sensation that I was wearing an ill-chosen costume, but as my other clothes were now a damp ball in my bag, I had no choice but to stick with the plan. I shuffled out of the bathroom. The dress even made me walk weird.

Lisa Bonet
(Photo by The LIFE Picture Collection/Getty Images)

Back at my seat, my friends took one look at me and their eyebrows shot up into their respective hairlines. “That looks…” Sarah began, barely holding back laughter, before Adrienne interrupted, speaking generously through visible alarm: “It looks really comfortable.” Yes, physically, the dress was comfortable; emotionally, it felt like a hair shirt. You could say I wasn’t pulling it off.

But as I watched the lead singer of Luscious Jackson bounce around the stage with an orange flower behind her ear, a thought occurred to me: Maybe pulling a thing off has less to do with drumming up the confidence to wear it and more to do with feeling like it actually lets you be you in the first place. Maybe items that appeal at first blush don’t always work for the you that you are.

At RFK stadium that day, I learned I was not and probably never would be a freewheeling twentysomething bralessly selling sundresses and hemp backpacks in a parking lot, and no dress I could put on in a stadium bathroom could make that not be so. But if the realization of my non-Bonet-ness was a disappointing one, it also brought with it a ray of hope because it meant I did have a discrete identity, one that I could explore through — among other avenues — the continual trying on and taking off of things. At that moment, a genuine sense of self surged through me.

This is not a call to remain in the comfort zone. In fact, in the 20 years since it occurred to me, I’ve found it to be quite the opposite. Trying out new stuff gives you valuable data. As with sleeping with the wrong person, you can’t know that some clothes aren’t right for you until they’re actually on your body. You may learn that you hate showing your midriff but really love hats. That you think kitten heels are trash. That nothing has ever made you feel more invincible than a wide-leg jean. So whether it impedes your natural movement, makes you sit weird or just makes you feel unlike yourself in a way you can’t quite pinpoint, toss that peplum blouse/PVC trench/Parisian night suit aside in favor of something that actually does. Why bother trying to pull off anything else?

Feature photo by Ron Galella, Ltd./WireImage.

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  • Adrianna

    Accepting that you can’t “pull everything off” is also a way to embrace the body you have. I was a teen in the 2000s, where the common style was basically for someone who is 5’10 and long-torsoed – I am neither. I couldn’t “pull off” low cut jeans and cap sleeves tees, and subsequently felt bad about my body. I took the time to try on a lot of clothing in department stores, and now I know what kind of dress silhouettes I can “pull off” and which ones make me feel uncomfortable

    • Alex

      It’s so interesting that “pulling off” often relates to how we feel in our bodies!

      My quest for clothes I could pull off, bizarrely, led me to completely ignore traditional suggestions on how to dress for my body type. For example, I have a chest/bottom ratio that is considered pear-shaped. Why in hell should I pretend I have bigger boobs? Why should I hide my lower-body “asset”? I enhance what I feel is worth enhancing, and I hide what I prefer hiding.
      I want to be my own shape!

      • Adrianna

        Now that you mention it, I mostly ignore that I have an hourglass shape. (large breasts and an ass.) Every style guide will tell me to put on something that cinches at the waist. I used to be obsessed with the fact that most tops and t-shirts make my midsection look a lot bigger – the fabric hangs away from my body because of my bust. But since age 26 or 27, I generally wear loose button downs. I love all of my black and white horizontal stripe shirts

  • Clare

    “As with sleeping with the wrong person, you can’t know that some clothes aren’t right for you until they’re actually on your body”– Amen, sister!

    Better to try something new, look silly, and have a good laugh with friends about it than to cling to what you know out of fear, losing the chance to find that one piece that makes you feel radiant!

    • Cynthia Schoonover

      I agree. You never know how something will look until you try it on.

  • Abbie

    I grew up being told constantly, “oh *I* could NEVER pull that off, but you totally can!” Which I never understood because a) it’s a backhanded complement and b) my clothes weren’t THAT weird. Just a little bolder than the typical midwestern outfit. “Pulling something off” stops and starts with you feeling confident in your own skin!

    • Ashley S


      every time someone says that I’m like yeah exactly that’s why I’M wearing it!!!

    • Sarah


  • Alex

    That’s the problem with trends, isn’t it? They’re so ubiquitous you want to try them and be one of the cool kids… Only to feel so uncomfortable, you couldn’t feel more anti-cool.

    For example, I can’t handle pastel colours and cute-looking or vintage-looking clothes. I am a small-sized person and that makes me feel like too much like a doll! On the other hand… Big hair? Bold makeup? Extravagantly structural monochromatic outfits? Anything black? They’re all a yes for me!

  • I think no one can pull ANYTHING off. My personal style is pretty weird but I can only pull off MY type of weird.
    At the end of the day, we have one personality, one body type, it makes sense that some things suit us and some don’t!

  • Stephanie Atlan

    I was at that Tibetan freedom concert! I was a sophomore in high school and we camped out to get tickets. And I remember what I wore at least the first day: a gray cotton halter top from urban outfitters and these sort of utilitarian shorts and converse and as soon as I got there I knew I was in the Wrong Outfit. I can attest that it was sweltering. My friends and I got stoned in the 420 seating section and I got mad at myself for being too scared to crowd surf.

  • Anything strapless or off-the-shoulder makes me look like an imposter. It doesn’t look *bad* necessarily, but when I see myself in the mirror while wearing something of that nature I definitely feel unsettled and uncomfortable.


  • Jessica

    I am this way with A-line midi skirts. Those floaty, light things that look so comfortable in summer, I just cannot get happy in. I feel like I am dressed up as someone else. I have accepted this now and completely given up on them.

  • DelphineGarnier82

    There are things that I can’t pull off that I don’t want to wear anyway. So it’s fine. I know what I like and I know what I actually want to wear. Some things feel more like wearing a costume than wearing an outfit. And I know some people don’t care about dressing for their body type, but personally it bugs me if I feel something I’m wearing that is badly proportioned on my frame.

  • tiff

    I relate so much to the suburban 90s girl with limited options that resulted in me mixing little boys clothes from Target with oversized mom accessories from department stores. I must say it turned me into one hell of a resourceful shopper! In my 20s, I was the girl who would wear anything…even for the joke of wearing it. It was the ‘fuck you’ boldness of naivety (coupled with a 20 year old body). But, there was a moment in my early 30s when I ran into a young girl wearing a captain’s hat and suspenders….looking stunning….that gave me a moment of harsh clarity. No amount of confidence or defiance would allow me to look effortlessly cool in a captain’s hat at this time in my life. It just isn’t me anymore. I can’t rock a captain’s hat. There, I said it. The solace in this is that there will most likely be a reversal of all of this when I hit 70+. I can’t wait.

  • Melissa

    No matter how many times I try on Doc Martens or how many years it’s been since I last did, I will never, ever look anything more than very short and stumpy.

  • Anna

    THE pant suit! How badly I want to pull it off. But my petite 5’2” frame disagrees. Oh well!

  • Abigail Pote

    The thing I love best about this article and most of the comments is how easy it is for all of us to get caught up in conflating “pulling it off” with “traditionally flattering”. I absolutely agree that there are some things individuals cannot pull off and it isn’t because it doesn’t “look good” on us, it’s because we don’t feel good in it and that discomfort plays into the way we greet the world. Reading this article was really confirming because there are so many things I like that I cannot pull off because it just..isn’t me. Which is an idea I was discussing with my sister last night and this was a much more concise way of discussing that feeling.