Monday Roundtable: Our Worst Haircuts

As we continue on with our But Make It Fashion issue, we look back on our worst haircuts because it was these failures and a bit of experimentation, that lead us to finding a style and look that truly works for us. Sometimes it was our fault in asking for a particular cut and sometimes it was totally the hair stylist’s mistake, but we were mostly horrified with the result. Here’s evidence of our biggest haircutting mistakes.


Carolyn Yates, NSFW Consultant

My worst haircut wasn’t on purpose. I’d been growing my hair out but it was feeling messy, so — because I’d just moved back to Montreal and was visiting my parents — I went to get a haircut with someone I’d never gone to before. I asked for the front long and the back short on a sharp diagonal (I described it better at the time, I swear). The stylist gathered my hair in a way that I assumed meant he was going to trim the ends, and cut off most of the front and a good chunk of the sides, effectively giving me the opposite of what I asked for. Afterwards, I went outside and chain-smoked and wept in the parking lot of that suburban Aveda, and then I made a hair appointment in Montreal for three days later, and then I went back inside and tipped that stylist because I felt like it was my fault for not saying anything. I do not have pictures of that haircut.

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Heather Hogan, Senior Editor

I mean I had a mullet my entire childhood and tweenhood. (Oh, does it look like I’ve been crying in that pink dress picture? That’s because I’d been crying because I was spanked because I wouldn’t wear it, which I didn’t want to do because I hated dresses and lace touching me makes me feel like my skin’s on fire! #fashion) I didn’t even grow my mullet out until middle school! And then in high school I grew out my bangs! And now I’ve had the same haircut for 20 years.

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Stef Schwartz, Vapid Fluff Editor

Back in 2007, I went into a walk-in shop on St Marks Place and asked for a trim. I had chin-length black hair and an undershave, which wasn’t a great look for me, but I was really into it at the time. Here’s the problem: the guy cut it WAY too short in the front. It was barely down to my nose! I’m super self conscious about my nose and my face in general, and without hair to hide in I feel exposed and panicky. Reader, I cried. I was about to go on a short tour with a friend’s band and just wanted to look cool! How was I supposed to hang out with cool band dudes when I looked so alarmingly hideous?!?! Somehow I coped with this by wearing a grey bandana the entire time, which also looked ridiculous, but I convinced myself it was better than showing the world this haircut. In spite of everything, the haircut eventually grew out, as haircuts do, and I learned a valuable lesson about trusting strangers with literally anything.

I don’t have photographic evidence of this per se, but years later I entrusted my hair to my good friend Hilary, who was actually in school to cut hair. These days I wear my hair long, with layers. Hilary enjoyed taking creative license, and no matter what I asked her to do she’d just do whatever she felt like doing anyway. One time, she gave me… the Rachel. I asked all of my friends to level with me and tell me if she did, in fact, give me the Rachel, and they all assured me that it was not. Only now, many years later, has anyone admitted that it was totally the fucking Rachel. I’m still scarred.

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Rachel Kincaid, Managing Editor

My hair has always been My Thing; it is very long and curly, it’s pretty, etc. Anyone who has ever wanted to compliment me or flirt with me has mentioned my hair; everyone I’ve ever dated has made a panicked face and then tried to hide it if I mentioned cutting it. This is fine, but there’s nothing like having a Thing to make you sort of itchy about having a Thing and wonder what would happen if you changed it, and also no one makes it through their 20s without wanting to chop all their hair off in a moment of emotional turmoil. When I was about 23, I did, in the middle of a big breakup and before moving across the country to a city where no one knew me. I went from hair past my shoulderblades to a Bisexual Bob, about chin-length. It was… fine. It was way easier to care for, without waiting seemingly days for it to dry, and it was still pretty. But I knew I was strapping myself in for growing it back in pretty much immediately. It’s my thing! I know myself.

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Alexis Smithers, Staff Writer

Thankfully my only bad haircut stories are bad weave stories which I think lends to that lesson of nothing is permanent or some such nonsense. I had this weave I think my sophomore year of high school that was just not my look but I didn’t realize that until literally a year later. I just look back like, what was on my head and why did I let it stay there?

I wanted it because it was Rihanna circa-Umbrella inspired cut but like I lowkey never took care of it so I can’t tell you when it ever looked like what it was supposed to. I didn’t have to grow anything out! Thankfully I just had to wait until my family gently told me, “maybe it’s time to switch it up,” which is code for “get this shit out now,” before I went back to braids. I didn’t cry because I barely looked in the mirror sophomore year (literally three weeks before I started sophomore year my grandfather had died) so I only remembered I existed as a corporeal being in little spurts. It was a strange and terrible and sometimes really fun and, unintentionally but subconsciously intentionally, gay time.

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Riese, Editor-in-Chief

This is the only picture I can find from that era — it’s super blurry and also like two months after the haircut so you can’t really tell how horrible it was but this is all i have. I’m in the middle!

As someone who literally landed herself in the emergency room over a bad post-breakup dye job, it’s truly hard for me to pick just one hair disaster. I’d say 50% of the decisions I’ve made about my hair have ended very poorly.

But the first, most glaring thing that comes to mind when I think, specifically, “Worst Haircut Ever,” is the haircut I got in the winter of 1995. If you were present on this planet for the winter of 1995, you may be vaguely aware of a trend at the time known as “The Rachel.”

The winter of 1995 was also when my Dad died, so I was like, really not doing well in general and did not need to add to the pain with a terrible haircut.

Here’s a thing about me: I’m Jewish. My Dad wasn’t Jewish, though, so my hair is only half-Jewish. This means it’s like, frizzy and curly and poofy in some parts, and then straight and boring in other parts? In order to pull off a Rachel, you really need stick-straight hair, or at least access to a straightening iron AND a curling iron, and I’m not sure affordable straightening irons existed on the consumer market at that point.

It’s face-framing layers, but they are VERY aggressive. I think I looked okay when I left the salon, but looked very bad immediately thereafter. My face-framing layers just wanted to be poofy and curled at odd angles so intensely that they almost became like five different layers of haircuts atop one another. Due to other trends at the time, I basically dealt with this by wearing hats and/or taming the situation with a variety of Hello Kitty and days-of-the-week barrettes. It was a tragedy.

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Archie Bongiovanni, Cartoonist

Some folks cut their hair off in one grand haircut. Not me! I took my damn time in getting a short cut and trimmed my hair into a multitude of different hair cuts, each cut getting shorter and shorter. Each cut was getting closer to the fade I actually wanted which meant a lot of in-between cuts. This is some sort of curly bob with some curly bangs. I’m not sure this hair is a disaster per se, but it does signify an in-between state for me. I was caught between what felt safe and gathering courage to get to where I wanted to be.

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Sarah Sarwar, Business Director

I felt very whimsical when I said yes to “baby bangs” in the hairstylist’s chair. But uh, not so much later. Luckily I was home from college that summer so I didn’t have to see any of the cute girls I was crushing on.

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Cameron Glavin, Cartoonist

Sometimes you’re a freshman in college and you FINALLY have the space to explore the many facets of queerness denied you at home. Sometimes you decide that one way to explore this queerness is in a dorm bathroom where you ask your friend to cut off all your hair*, BUT NOT TOO MUCH — you don’t want to completely look like a boy — just enough to look like you got into a fight with a mild-mannered weed-whacker. In the moment, you’re silently horrified. It looks terrible and you hate it. You look back at it and it still looks terrible and you hate it, but it ALSO looks like a big wobbly-baby-giraffe step toward a self-made Self.

*I asked her to do this SPECIFICALLY for a drag show we were going to be in. I thought this was a great whim to follow, and definitely in line with my personality. It was neither of these things.

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A.E. Osworth, Contributing Writer

I paid $30 for a men’s haircut in NYC (that’s a small amount in this city) with a barber I had never met before and told him to do exactly the thing I always get. I get my part razored in, and he said this was no problem, but I knew I made a terrible mistake when I saw HIS face reacting to the way he’d just cut my part in. Sure enough, my part started normally, expanded in the middle, and then tapered back down to a normal width. It looked like a snake who’d just swallowed a rodent in its entirety. I did not cry in the salon and I still tipped him because I’m not a monster — but when I got home, I cried and called my mother? I’m adult and I’ve never cried over a haircut before and I don’t usually call my mom when I’m sad or frustrated or mad. She asked to see a photo of it. I sent her one and she asked me if the man hated queers, because this was clearly a hate crime.

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Siobhan Ball, Contributing Writer

I was about three years old and a big fan of The Magic Roundabout, in which Florence had got a very fashionable bob cut. It remains a mystery to this day why the childminder and the hair dresser she’d brought me to “for a little trim” believed tiny child me when I insisted I was meant to get a bob. Apparently my parents were wonderfully horrified when they got home. I was also unimpressed as I hadn’t understood what a bob actually was and while my gender presentation swings around wildly, one thing I’ve been consistent on is long, long hair.

As I also mostly wore jeans and the tiny biker jacket my godfathers had got me at this age, everyone who’s ever seen the picture’s of little me says something along the lines of “I didn’t know you had a little brother.” Tiny me says smash patriarchal gender norms but also this hair cut was a mistake.

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Molly Priddy, Staff Writer

The worst my hair ever was, in my estimation, were the couple years before I got the nerve to demand a shorter cut. I knew I didn’t feel comfortable with long hair, that I wanted something short and easy and that fits more to how masculine I feel inside. These photos are from when I’ve had haircuts from people in a small town who didn’t believe me when I said I wanted it short, who said you can’t be serious, are you sure? And I was, but I was afraid to say so, to say I wanted the weird thing. I also knew it would mean I’d be much more easily identifiably queer in a conservative place. But I’m proud to say now that I’ve taught no fewer than three hair stylists that it’s ok to cut a woman’s hair short-short, and that they can believe me when I say it’s what I want. That was big for me, so I particularly hate this era of hair, 2 B.C., or Before Confidence. bmif tombstone


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59 Comments

  1. My worst haircut was last year when I was ill with anxiety and changing meds and in no state to go out but my hair had got to the length of “this needs to go before I shave the lot off”. So I tried to cut it myself with clippers in the mirror because how hard can it be right? I have no coordination in the mirror and got my angle wrong and it was a disaster of semi-bald patches. Thankfully I decided to stop after doing the back so I couldn’t see it unless I used two mirrors and could pretend to myself it was fine. When I finally got to the hairdresser a month later she took one look and said “promise me you won’t EVER cut it yourself again”.

    • I did something similar, but with a Bic razor.

      It looked like I got attacked by a not-so-mild-mannered weed-whacker.

      I swallowed my pride and went to the hairdressers and the only way to salvage it was to shave everything off except for a teeny patch of hair on top, a very radical look in 1985.

      I was secretly very pleased. All’s well that end’s well, I said to myself ! But that was the end of the self-haircut for me.

  2. I’ve had so many terrible haircuts from the 1st grade “we’ll save money if I cut your bangs myself” horror (thanks Mom) to the 7th grade “I want to look like Joan Jett” request that ended up being a sad mullet to the other week when I told my stylist I didn’t want to see the sides of my head and he cut off the longer top part anyway. (I have no appropriate words to describe hair, sorry.)

    However, Siobhan Ball, the hair and pic here are precious and I want to squeeze tiny you and buy her ice cream!

      • Tiny you is adorable, I just wish we’d gotten to see the biker jacket too. I am also sympathetic because my mom kept my hair quite short (like ear-length) til I insisted on growing it starting in sixth grade. I got misgendered several times and tiny-me hated it because tiny-me logic went like “Everyone knows boys are categorically not-pretty, therefore if someone thinks I am a boy they think I am not pretty, therefore I am ugly.”

        Sounds like you had awesome godfathers.

        • There is a photo of me in it pushing a toy wheelbarrow around but I don’t have a copy sadly and didn’t feel like explaining to my granny what this was for lol.

          My godfathers are very awesome. They’re both guitarists that played local gigs and session music when they were younger and back then they went everywhere on the one motorbike.

  3. I went through junior high and high school in the 80’s. I have nothing but school pictures of regrettable decisions. Big hair and mullets. I was the stuff at the time, but looking back I wonder what we were thinking.

    • I just laughed out loud in the break room. 80s hair styles really don’t hold up well.

      There’s no photographic evidence of one of my sillier HS 80s hair styles – I had a tail. And I loved it.

      #olderstradder

  4. I had my hair cut short once and I was happy with the result until my GF started crying that my curls were gone and said, “Well, it’ll grow back out.”

    My mom is a hairdresser and when I was a long ways from home once and broke she told me to put my hair in a pony tail and then put another hair tie further down about the length I wanted it and to just cut it all off after the 2nd hair tie since curly hair is pretty forgiving if your ends aren’t straight. What she failed to mention was that you should put the pony tail as low down your head as you can instead of up higher like I would normally wear it. But the result ended up being unintentionally cute: longer in the front, shorter in the back.

  5. I love bangs but I have a super small forehead and a lot of volume, so I can’t pull them off. I love bobs (duh, I’m bi) and at least once every two years I’ll get one. Usually in front of my bathroom sink, at 2 am. This year I managed to convince myself into getting a lob, and it’s longer on the front, but every couple of months I take a couple centimeters off. I love short, straight hair but that doesn’t go with my hair texture so I gave myself an undercut and for now I’m happy with it.

    My worst haircut is probably when I was 12 and for some reason felt very cute with my shoulder length hair, which I styled with middle part and three butterfly clips on every side of it. It went swimmingly with my round fat face and acne.

    • Butterfly clips were the shit! I was around 12 when I got a shoulder length haircut with bangs—taking it up from the just-let-everything-grow-into-a-long-triangle-shape-down-my-back-? and I felt like the new hotness. My sweet cousin bought me some butterfly clips when we visited so my style could really be on point. My father saw my new cut and said “ok, just don’t cut it any shorter” and explained he never liked it when my mother cut her hair short. Now I have a fade, and once again am the new hotness.

    • sidebar: do you ever reply to a comment wanting to build someone else up and then once you’ve submitted it, realize that you had a lot of shit to work out that you just brought along? Apologies. And long live butterfly clips.

  6. Step mother number one went to cosmetology school and my dad and I were her practice hairs. One time we both got perms and ended up looking like late Brady Bunch dad Robert Reed. Twinsies! Look it up on the internet for the visual. There is nothing worse than a gentile with an unintentional afro.

  7. my hair is curly enough that if I don’t brush it/ruin the curls in some other touch related way, no one can tell if my hair is cut well or poorly. I’ve always had longer hair but honestly people didn’t even notice when I cut it from “mermaid hair over my boobs” to “shoulder” length this october. ignoring all the times I cut my own bangs in Middle School, High School, College, and post college (I do not learn) i think it’s possible I’m moving into worst hair cut ever territory right now. I honestly REALLY want an undercut and i’ve started getting little bits shaved from the back and side. But the top layer of my hair is very dry and frizzy with my favorite curls making up the bottom layer. Is top undercut a thing? I think i’ll likely end up with some kind of “very short all over except a mess of curls on the crown” kinda thing

  8. I’ve had a litany of bad haircuts including the Weed-Whacker Special mentionned above.

    My most recent memorable experience was my ex and I going to a very expensive supposedly creative salon to get our hair cut by two different stylists, on two separate floors, and ending up with the Same. Exact. Haircut. When we were paying at the cash register we didn’t know whether to laugh or cry. I think everyone was equally stunned by the implication that this salon was not, in fact, creative at all.

    After that I was so discouraged I just let my hair grow out for over a year. Long hair unfortunately brings out the sadness in my eyes so, not a good time. Thankfully I’ve found a good barber now ! Twinkling again.

  9. When I was 14 I was obsessed with Jennifer Love Hewitt and I wanted bangs like hers, well she has very fine/thin hair and I have very thick hair needless to say the bangs just looked awful.

    And another time was I used to get my hair cut at Sears Salon and one of the hairstylists only cut half of my hair so the left side was long and the right side was a bit shorter. I have no idea how my mom or I didn’t catch this until we got home. I ended up cutting it myself to try to even it which was a terrible idea and ended up wearing it in a ponytail until my hair fully grew out.

  10. My hair has been compared to expensive Persian rugs(we don’t cheap out on rugs, especially Persian rugs) as a kid; so, I am not sure to be offended or say thank you cause I know people who have rugs the price of the cheapest car in North America. So, when it grows out it’s like Jewfro but even smaller curls, and feels like a rug. All my haircuts are one way or anther bad cause any style I see in person or online can’t really be done. One year my cousin took me to his fancy stylist to get a cut and my hair straightened but because it’s me straightness only lasted half a day. My the next day my buddy was like I can’t tell the difference and you just wasted money for no change.

    • so i had like shoulder-length blonde hair and i had a breakup and i was VERY upset about it, except it was a breakup wherein my ex didn’t want to be my boyfriend (because, i learned later, he had acquired another girlfriend!), but did want to have control over my life and did not want me to date any other boys or even like, be in the same room as another boy in a social setting. especially this one boy, paul, who liked brunettes. so one day after a bad fight with my ex i bought a box of feria and dyed my entire head dark brown instead of blonde.

      i looked like elvira and kind of hated it, but whatever, i did not give a shit! i was very depressed! and then my ears got kinda red? I can’t remember the time period that we were dealing with here but 24 hours or so in to the whole thing, my head was red and felt like a marshmallow and my ears were bright red and swollen and it itched and was terrible.

      my ex picked me up from the party i was at b/c paul was there and i was like, lol i think something’s wrong with my head and he was basically like, yeah this is what you get for dying your hair dark! you should be blonde. I felt like my head was gonna pop off my body.

      anyhow i went to the ER and sat there forever and then i guess what happened is that i’d had a bad allergic reaction to the dye. this was weird to me because i had dyed my hair with box dye like a million times. as soon as the swelling went down i went to the mall and they cut off most of my hair cause it was so fucked and did the rest in chunky blonde highlights. i looked great!!!!

      if you think this stopped me from ever using box dye on my hair again, you would definitely be wrong! i had a few more mishaps until 2011, when my head got red and itchy and swollen again from a really terrible dye job (it was like, bright orange) and then i was like okay it’s over, i can’t do this again, it doesn’t count as a budget situation if it takes up a whole weekend of drama and inevitably leads to a $300 color correction incident.

  11. When I was in middle school, all the boys I was friends with cut their hair to look like Nick Carter from the Backstreet Boys and I did, too. The only problem was my hair isn’t really straight or curly. It’s just kind of wavy so I could never get that perfect middle part that Nick and my friends could. It would be straight on one side and then the other side would do this little flip out to weird angles. And to 7th grade me, this was truly mortifying.

  12. Alexis Smithers I loved your story. <3

    I loved how people talked about acquiring the confidence and knowledge to be their true selves. <3 <3 <3

    I have hated getting haircuts my whole life, until finally a few years ago I just bought some clippers and youtubed it.

    Friends, I fucking love cutting my hair now, and it's one of the most empowering things I do for myself. I love my haircuts.

    There's hope!

  13. Most of my elementary school pictures show a little notch in my bangs, like a lost tooth. I have a cowlick and I guess my bangs were always cut wet and when they dried that tiny piece would bounce up just a quarter inch further than the rest. These may have been the best haircuts though. Ramona vibe. Very me!

    I had a haircut a lot like Cameron’s. It wasn’t the worst though! Knowing I was going to get a short cut I took liberties and cut a “bob”.

  14. I can’t call it a haircut because it was my *style* from about 7-10 years old–but I used to wear a long braid down the middle of my back to my waist and then I had curly bangs.

    I like to call this hairstyle LongBraidCurlyBangs

    There is little photo evidence because as a baby queer I went and cut myself out of all my family photos during this time and now that makes me very very sad

  15. ok this isn’t MY worst haircut story but….four days ago i gave my sibling THEIR worst hair cut. they have essentially an undercut and were like ‘hey gimme a trim’
    like a fool i acquiesced
    i had never used a hair trimmer! i warned them of this! and yet we persisted!
    it was going fine after the first round but when i took the guard off to clean all the hair bits out…i did not put it back on. and then i shaved a large chunk out of their hair.

    long story short they have a to-the-scalp buzzcut with a giant plume of turquoise on top, are still kinda pissed at me, and i am no longer allowed to give haircuts

    • ahahahahahahahah classic thank you for sharing this delightful story.

      I live in fear of the knowledge that one of these days I will definitely use the clippers on myself without the clipper guard. Reverse side mohawk, you are my destiny.

  16. The way my hair looked wasn’t bad, but the haircut experience itself was bad and left me with a life long distrust of people who cut and style hair.

    It was the first time I can remember feeling violated, someone imposed their will on me for the assumed benefit of another person and ignored my will, my agency entirely. I didn’t matter, old enough to be responsible for doing my own hair, old enough to give confession in church, old enough to testify in court and to this person I didn’t matter enough to warrant any consideration. I wasn’t a person to her.

    She decided of her own accord that she’d do my mother the unasked, unwanted “favour” of giving me a bob when a trim is what was requested and agreed upon.

    I couldn’t be consoled with “it’ll grow back” and couldn’t articulate well enough why it was so upsetting beyond vowing to never let anyone else cut my hair ever again. It was funny story of how dramatic and hysterical kids can be over the silliest of things for awhile, and the fucked up part about that was my mother had enough awareness of my feelings to avoid telling the story within my earshot.
    And I know if I try to explain with my grown up vocabulary and understanding of consent it’s still going to be “funny” because a child’s consent is that trivial.

  17. My worst haircut was this style, which I wore for 12 years:

    My mother chose the cut for me when I was a baby, and I wasn’t allowed to grow it out until I was old enough and responsible enough to wash and care for long hair. It resulted in a LOT of gender mix-ups, so I grew it out as soon as I was allowed to, but by then I wore small round-ish glasses and instead of looking like a teenage girl I just looked like, and was called around town, John Lennon.

  18. I had the “growing out a buzz cut” mullet for a couple of years at the end of high school/beginning of college, which became the “is this long enough for a ponytail yet? not really, but I’m gonna try anyway” look. Was I allergic to regular trims??

    There are no pictures of what I briefly looked like when I was 4 and cut my own hair, resulting in my dad trimming the sides to make it even and leaving the back for some reason?? They only left it like that until everybody else needed haircuts too. But at 4 I was immune to shame, so nothing tops the awkward mullet/Padawan ponytail.

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