Can everyone tell I don’t usually wear hats?
How to cure fashion imposter syndrome with stylist Kendall Flavin
Years ago, a meme came across my desk that put something into words I had always felt but never said aloud: Can everyone tell I don’t usually wear hats?
I was stunned. Could it be possible that everyone else in the world shares in my personal fear of looking like a hat amateur? The feeling that the barista and the mailman and the kids on the bus are all giggling behind my back at how inauthentic I look in a baseball cap?
At this point, versions of this phrase pop up on my feeds constantly. So I’ve called in stylist, writer of
, and expert fashion yapper to have a discussion about this silly and seemingly universal feeling. Let’s break down Fashion Imposter Syndrome.
How would you define Fashion Imposter Syndrome?
MacKinley: I describe it as the feeling that everyone knows I don’t usually wear a baseball cap. (I previously always referred to it as Baseball Cap Syndrome for that reason, though I’ve renamed it Fashion Imposter Syndrome to be all-encompassing.) It’s a self-consciousness unique to the experience of wearing an accessory or item of clothing you don’t feel is totally you. You’re not used to seeing yourself in a baseball cap, so you assume others aren’t either.
In reality, of course, people passing you on the street (or even your closest friends) don’t keep tabs on the frequency of your hat-wearing. It could be the first time you’ve ever worn a hat in your life and 99% of people will have no idea.
Kendall: Exactly what you said. It’s a bit of “I am trying too hard” and a bit of “everyone is judging me,” when in reality 99% of people quite literally do not care.
What item of clothing or accessory gives you the worst case of Fashion Imposter Syndrome?
K: I think I’d have to say any sort of “elevated” skirt or dress. I am a denim girl through and through, so that is my comfort zone. A long linen skirt is one of the few exceptions to this. I have a few skirts and dresses that I feel are too “extra” and like I am trying too hard — I finally wore one of them for my birthday though! And I had a number of people tell me they loved the skirt and the outfit, so it really is just a mental block I have to try to get over.
One of my all-time favorite sample sale purchases, a Tory Burch runway sample, has never left the cocoon of my closet. (See photo below.) The dress is stunning and the details are right up my alley — a huge collar, a pleated skirt, sequins. But put it all together? I feel like everyone in their mind is going “oh, she’s like a little kid playing dress-up.”
M: It’s so crazy because, as an outside party, I see that dress and just go “that’s SO Kendall.” I’d never give a second thought to you wearing it, I’d just be thinking '“what a great piece that suits her style so well.” Further proof it’s all in our heads!
I really relate to this sentiment though as someone who also reaches for comfortable denim the vast majority of the time. I wish I could withstand a bit more discomfort in my day-to-day wear, but I’m kind of a baby about things that itch or rub or snag or (especially) give me blisters.
I’m trying to afford regular everyday errands the same respect as a night out. If I’m leaving the house, I might as well make it worth my while.
One of my favorite things about living in New York City is that you can wear the fanciest thing in your closet out to coffee on a random Tuesday morning and hardly anyone would give you a second look. I think my penchant for comfort precludes me from utilizing this to its full potential. But if I saw you in this Tory number grabbing a matcha latte I’d make a mental note that you were the best dressed in the room!
K: Huge emphasis on comfort hindering my ability to go outside of my comfort zone. But also I agree 100% with New York being the perfect place to throw on your craziest look to run errands. Over the winter I bought a floor length red wool coat and immediately wanted to wear it — so I took myself out for coffee. Sometimes you have to give yourself an “event” to wear things to, but I’m trying to afford regular everyday errands the same respect as a night out. If I’m leaving the house, I might as well make it worth my while.
I also think of that one Carrie Bradshaw tulle skirt she wears in Paris. I would love to wear a skirt like this, but for some reason I can’t get myself to walk outside in it. However, if I ever see someone wearing this or something similar I immediately think she looks the absolute chicest and am incredibly jealous of her confidence. No judgment on my end, just awe. We are our own worst enemy.
Also, headscarves. It’s something I’m working on. I’m thinking headbands might be a good entry point. (Not Blair Waldorf, more of a wide jersey band.)
M: Absolutely to the tutu — I have one sitting in the back of my closet right now that a friend gave to me, but I just haven’t worked up the courage to wear it yet. I wore tutus all the time as a kid, so there’s definitely a confidence lost as we grow older and become more self-conscious of our outfits. I could relate it to the idea of women being socialized to take up less space both literally and metaphorically, but that’s a whole other letter.
When I put on poofy silhouettes I always think “now how is this going to fit on a crowded subway car?” and that sometimes prompts me to change. I’d hate for my tutu to spill onto someone’s lap and ruin their commute lol.
I certainly had a bad case of Baseball Cap Syndrome (with actual baseball caps) a few years ago, but I can happily report I have been cured after loooots of exposure therapy. It’s really just about getting used to seeing yourself in it. A longtime enemy I have yet to shake — eyeshadow. I never wear eyeshadow and feel like a clown with any on. A bold lip I love, but for some reason the eyelids are where I draw the line. And it’s so silly because I have friends who wear eyeshadow daily but feel clown-ified by a bold lip, but I think they would look amazing with a bold lip.
Why do we convince ourselves we can’t do such silly things like wear a baseball cap?
K: This may be a cynical take, but I think a lot of it stems from the social media effect on our wardrobes and personal style. A lot of us, even subconsciously, want to be liked and accepted. This isn’t just because of social media, but I think this has hugely exaggerated this whole idea.
I would wear satin bubble skirts and chunky turquoise J.Crew necklaces and literal heels to school when I was in middle/high school and didn’t think twice about it. Now, the first thing we do is check our feeds in the morning. And as a result, we base our looks on what is popular, often going so far as to completely copy looks from people we deem more stylish with more access to luxury pieces and PR. If we do as they say, maybe one day we can be them. We have to remember that these people are being paid to sell products!
M: As corny as it sounds, I’m so nostalgic for a pre-Tiktok internet. I loved watching Youtuber hauls and reblogging outfits I liked on Tumblr without the websites actively trying to get me to add-to-cart mid-video from a link in the bottom left corner.
While I’m positive people throughout history have always experienced some level of self-consciousness about their clothes and facial features, social media has created a type of surveillance state that has magnified these fears to an unprecedented level. We’re all at risk of being filmed or photographed in public at any time — and god forbid someone post a bad moment to Reddit or Tiktok and we become the internet joke of the day. Everyone is perceiving and being perceived way too much. And I think that naturally leads to something like Fashion Imposter Syndrome, where we all start to anticipate strangers’ judgment about something as trivial as wearing a very normal hat.
And why is this feeling sooooo universal? It feels like I see or hear it brought up constantly, both online and with friends irl.
K: I went on a bit of a tangent above, but I think that applies here. It’s also easy to fall into the trap of listening to those around us. Hear me out! This is not necessarily a bad thing, but we, as humans, put a lot of stock into the opinions of others. My best friend and I will send photos back and forth and I might hate something she wears and vice versa. I just bought cobalt blue sneakers, and she hates blue. She told me as such. I bought the shoes and I love them.
Fashion is supposed to be fun, and I think we also put too much pressure on ourselves to look perfect all the time. So what if something isn’t the most flattering thing on?
I fully endorse telling your friend you think their shoes are ugly and I fully endorse saying idgaf and letting it roll off your back when your friend says your shoes are ugly.
I also think it could do with our perceived aesthetics and views of ourselves. I’m writing this from a cafe and people-watching as I write — I just saw a woman walk by in a floor length linen sundress and huge woven hat. The first thing I thought to myself wasn’t “omg, why is she wearing that hat?” It was, “wow, she looks so cool.” But I also immediately grouped her into a sort of bohemian category. That might be who she is today, but tomorrow she could be wearing a full suit and loafers. We have to let go of the idea of one singular aesthetic and let ourselves experiment and have fun.
M: I fully endorse telling your friend you think their shoes are ugly and I fully endorse saying idgaf and letting it roll off your back when your friend says your shoes are ugly. My mom and I have such incredibly different tastes in clothing and home decor and we’re constantly saying “that’s so hideous” to each other — but I wouldn’t have it any other way! I think that honesty (when supported by love, of course) breeds an unbreakable self-confidence in our own style choices. Who cares if they love it? I do!
How does being a stylist influence your perspective on Fashion Imposter Syndrome?
M: Your job is to curate outfits to achieve a goal (whether that be create a fantasy, sell a product, tell a story, etc.), so you really have to analyze them from an outsider’s point of view — i.e., how will the customer perceive this look. In your professional opinion, is anyone really staring at our baseball caps and whispering about how they can tell we never wear them?
K: No! If anything, they are probably thinking to themselves, “I wish I could pull that off.” Styling is all about creating a vision (and usually selling something beyond just a look — it’s selling a whole lifestyle). It’s about being aspirational and telling a story. And a lot of the time, no matter the capacity — editorial, commercial, personal — the first concern is how we will be perceived, not how we perceive others.
M: You totally hit the nail on the head because when I see someone in public wearing something a bit funky or risqué, the only thing I’m thinking is “wow they’re so pulling that off.”
How do we combat this affliction in our daily lives?
M: I think trying it out in low-stakes settings can be really helpful, like a holiday, for example. Vacation You isn’t the real You, so why not add a little headscarf to this fun holiday version of yourself?
Maybe wear your crazy accessory somewhere like Times Square where it’s impossible to be the weirdest looking person in the vicinity; or maybe a literal baseball game (or wherever is deemed the most normal place to wear your accessory); or somewhere you won’t know anyone/maybe even will have a miserable time already — like the DMV — so you can desensitize yourself to the accessory in a place where you don’t care how people perceive you.
K: I definitely support the vacation theory. I wear headscarves and heels and silky maxi dresses on vacation that I would never wear somewhere like work or to the grocery store. I do however wear a lot of baseball caps to the office. Maybe too many. I should probably blow out my bangs more often.
I think everyone is a bit afraid of being too out there, so rather than judging, they might be secretly envious of your confidence and willingness to experiment.
My dad definitely judges my vacation looks — no, I didn’t need to wear satin mules and a giant gold buckle belt to dinner at The Conch Shack. But I did it anyway. I think this is also a great way to start stepping out of your comfort zone — a bit of exposure therapy, if you will. Throw on one item you might be unsure of in the comfort of your home with people you already know, because it’s way easier to be comfortable around them no matter if they joke about your outfit. So what? Everyone is having fun, and if anything, it makes you better at saying “fuck it.”
M: That reminds me of that internet joke where girls say “I know my outfit is good if my boyfriend hates it” (which I don’t love because I think your boyfriend should be obsessed with any outfit you have on) but instead of boyfriend it’s family members — that I can get behind. Any strange looks from my college-aged brother and I know that my outfit rocks.
K: I know if my sister rolls her eyes when I unpack my suitcase I’ve done something right. And honestly, it’s kind of fun to antagonize your family with excessively dramatic outfits. I’ve noticed, also, that once you finally take the plunge and wear those pieces you are scared to wear, you get tons of compliments. I think everyone is a bit afraid of being too out there, so rather than judging, they might be secretly envious of your confidence and willingness to experiment.
Or, make up an excuse to go outside of your comfort zone — dinner, a trip to the opera, anything. Once you get comfortable dressing up for occasions, I find it easier to let that bleed into your day-to-day life. I recently bought a huge statement necklace (thanks,
!!) and felt so stupid wearing it. And yet, everyone I met complimented it. The barista at my local coffee shop told me it was art. A girl shouted at me from across the street! My mom said I always manage to put together outfits she would never consider, but always loves. At the end of the day, we are our own worst enemies. I have yet to wear a babushka scarf to the office, however. But I think I’ll try to ease myself into it with a scarf headband and hopefully eventually work myself up to full pirate-styling.
M: There’s no better feeling than being unsure of an outfit and having someone in the wild compliment you on it. I think we subconsciously view other people taking outfit risks as permission to do it ourselves, which is why it can be hard for people to buy into a specific trend or silhouette or color until they’ve seen it on someone like their favorite influencer.
I think it makes us feel good to see other people making bold fashion choices. It’s like a green light to allow ourselves to take our own intimidating styling risks. Perhaps we need to reframe the fear of wearing loud colors or risky accessories — what if we view it as the honor of giving someone you encounter the permission to be just as bold?
We’d both love nothing more than to hear about your own cases of Fashion Imposter Syndrome, so leave a comment to keep the chat going <3
Kendall’s impeccable curation of summer necklaces.
MacKinley on sheer skirts and Lorde’s new album cover.
 | A guest post by
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Two of my very favourite people collaborating?! Be still my heart! ♥️
I knew you both would have excellent advice. Both exposure therapy and pushing your comfort zone work so well!
This is completely true! I dress up to grocery shop!
“Once you get comfortable dressing up for occasions, I find it easier to let that bleed into your day-to-day life.” 💯
Brilliant article! Wear it! No one cares, AND they’re envious you’re pulling it off. And then, share the experience and encourage others.💕