What’s the Biggest Risk You Ever Took with Your Hair?

Published in: Hair, Just For Fun

What’s the biggest risk you ever took with your hair?

Mine was right after a traumatic breakup in 1999. On a heartbreak whim I asked my stylist to chop my long black hair, which was down to my elbows, into a chin-length layered style with the ends flipped out.


But because that wasn’t enough of a change to purge my emotional demons, I went back the following week and asked for chunky red highlights.

I remember how liberating it felt to transform my look. It was like letting go of all of that hair somehow unloaded the baggage of my failed relationship.

Of course, I also remember how much of a pain-in-the-arse it was to grow out the new cut, LOL! I hate how my hair feels when it’s in that mid-length stage, creeping down the back of my neck.

What’s the biggest risk you ever took with your hair? Let me know in the comments. And try your luck with the Makeup and Beauty Blog slot machine (click the BET MAX button to play). Have fun and good luck!

Your friendly neighborhood beauty addict,



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  1. Christina says:

    I think the biggest risk I ever took was copying Halle Berry’s short-short pixie cut back in high school. A PAIN — constant trims and a horrible grow-out phase.

    But my biggest post break-up risk was carelessly choosing a box of hair color and allowing my friend to dye my hair. I was going for moody dark brown, and ended up a redhead (still not sure how that happened). Worked out okay, but definitely a surprise!

  2. Michelle says:

    The biggest risk I took was adding highlights. I have black hair and I just assumed the colorist would do natural highlights, like maybe a reddish dark brown, since that’s what color my hair looks in the sun light anyway. No, she gave me blonde highlights. I still cringe when I look back at those photos 🙁

  3. tanya says:

    I was six years old and I allowed my mother to cut my hair. Bowl Cut and all, I am traumatized by it still.

    tanya´s last blog post..pops of pink

  4. jess says:

    my craziest experience was last November, i was tired of my elbow length hair ,and one day decided to take my own snipes, and snip it into a Katie-esque hair ! It turned out pretty nice , and to avoid awkward questions i told people i donated my hair:) they sucked it up!

  5. Arianne says:

    I recently just got bright red highlights all over my head. Loved how it looked fresh out of the salon, but 10 days later (today), I am with reddish brown highlights.

    Will re-dye it though. 🙂

  6. RetroRiotGrrrl says:

    I’ve taken a lot of crazy hair risks but none have been too traumatic so far luckily!

    I dyed my light brown hair comic-book blue black (LOVE IT! still keep it this color)
    I’ve cut my own hair several times and none have turned out too disastrous actually several of my friends asked me to cut their hair after seeing my coif
    And cutting my own Bettie Page bangs (yes this is different than cutting your hair its twice as risky but now i always do my own I know just how i like ’em and its wayyy cheaper!)


  7. Dao says:

    I think the biggest hair oopsie I’ve ever had was when I let my cousin do my highlights using the stuff from a Revlon at home highlighting kit. The color was supposed to be copper but turned out to be moody emo weird orange red. On top of that, it was near Halloween so my other cousin said it would be a very good Halloween look!

    Dao´s last blog post..A Sale Announcement and an Update

  8. Violet says:

    When I was a senior in high school, I had shoulder length hair and I got it all cut off into a short Halle Berry style cut. I did it over the weekend and didn’t tell anyone about it. It was so much fun to see everyone’s reactions on Monday. 🙂 After that I had various short hair styles for a while.

    At some point, I started to grow it long again. Back in 2007 I had my hair past my shoulders and did another major cut into a Victoria Beckham type bob. I’ve kept my hair short since then and I have a layered bob right now with bangs.

    I prefer short hair and I think I’ll keep it for a while. I think the only other drastic change I could do now would be to color it some wacky color. My hair is jet black an I’ve never colored it before, so that would definitely be a risk!

  9. wendy says:

    Years ago I took a perm in my hair, it was afwull, I looked like a poodle. After 2 months a asked the hairdresser to straight my hair again. That was a big risk, because my hair could have been very dry after it, or break, but lucky me, it just worked out fine.

    ** Have a wonderfull weekend Karen!!**

  10. lesley says:

    I’ve always had my hair long and last year in June I chopped off almost 12 inches and donated it to Locks of Love. I’ve been rocking a Bob/Long-Bob “Lob” since then =) It’s really refreshing! But I’m still not used to styling it, so I really only have about two or three looks with it: all down, half up, and all up in a ponytail. LOL. 🙂

  11. gio says:

    The biggest risk I took was dying my hair blonde. It didn’t turn out too bad, although it made me look slightly washed out.

    gio´s last blog post..Know Your Ingredients: Niacinamide

  12. p. potter says:

    The day before I started my freshman year of high school I decided that I wanted a new, more mature look. So I dyed my light blonde hair chocolate brown.

    My mom called the hairdresser for an emergency Sunday appointment, and my locks were bleached for the first time.

    Needless to say I started high school as a blonde.

    p. potter´s last blog post..FOTD: The Green-Eyed Monstress

  13. Karen B says:

    When I was thirteen I wanted to go to the hairdresser and my mum kept on complaining that I always just cut a couple of inches off so my teenage self decided to go for a pixie cut… LOL. Not only was it not really flattering to my round face, it was HORRIBLE to grow out!!

  14. Well I already told you about one of the crazy risks I did so I’ll tell you of another. About 4 years ago when everyone (Reese, Gwenyth, etc.) was dyeing their blond hair chocolate brown I wanted to do the same. My hair had been many shades of red and blond until then but nothing super dark. So I had it done and man it was DARK! I mean to my eye it might as well have been black it was so shocking. It took me a solid week to get my eyes used to it but people at work were blown away and the hubbie didn’t like it. It did start to mellow out and fade a bit by week 3 or 4 but by then I already decided to go back to blond. So 6 or 8 weeks later I started the long hard process of going back, which is never as fun and immediate as going darker, LOL! The only good thing about hair that dark on me was that it made my blue eyes really stand out.

    Vampy Varnish´s last blog post..Rimmel 60 Seconds Spring 2009

  15. Solé says:

    I’ve always been willing to take big risks with my hair. I have a playful attitude about it and I always love a drastic change. I’m lucky that a wide range of colors look good on me from ivory blond to auburn (current color). I’d say the biggest risk I’ve ever taken was about a year after my divorce six years ago. I cut my elbow length hair into a chin length bob but the new cut wasn’t edgy enough for me. The hairdresser had been too cautious, expecting me to have post-chop regret like most of his other customers.

    I began thinking of what to do with it next when I was at a party and ran into my friend’s younger cousin. He had a great emo do (please keep in mind this was five years ago). I asked him who cut his hair and he said he cuts it himself. I then agreed to let him cut my hair into this crazy choppy asymmetrical do and we did it right there at the party. It was awesome. Some people at the party thought I was drunk but I’d only had one or two drinks. He actually cut it for me three more times in the following months before I decided to grow it into a Victoria Beckham do.

    These days it’s long again but I’m bored to tears. It’s looking like this spring will bring another drastic change. Good thing my husband doesn’t bat an eye at my impulses.

  16. Melia says:

    The biggest risk I took was when I was 16, I dyed my elbow-length dark brown hair, ginger-blond-red (it was reddish blond in the shade and bright ginger-red in the sun). I spent 6 hours for the colour change to take place and when I saw the results, I ran home and washed my hair 3-4 times with a clarifying shampoo to tone that colour.
    It didn’t stop there, as after 2 months, I chopped off my hair to an asymmetrical bob.
    Needless to say, I have never cut my hair like that again or tried to dye it any kind of blond or red again!

  17. Alexia says:

    Biggest risk I ever took was chopping it off and bleaching it pretty much close to a white blonde. My natural hair color is dark brown and my hair was pretty much in the center of my back…….I can’t front though…..It looks HOTTTTTTTTT!!!!! =)

  18. Heidi says:

    The biggest risk I took with my hair was by tossing the hair iron out the window and finally embracing my natural texture. At 18, I accepted my wavy hair for what it was and decided to say goodbye to my hair ironing/chemical straightening days. I’m so glad I did because I LOVE my hair now.

  19. Tali says:

    Im tanned and have dark hair (think female orlando bloom)
    and when i was 16 I dyed my hair blonde. VERY VERY BLONDE! It lasted 4 years.

    In theory i should have looked nuts.. in reality it actually suits me better. 3 years later people keep bringing up that i should go back. I now have blonde highlights and ive noticed my hairdresser makes me blonder each time!..

    I did one cut my hair to a pixie but which was so cute.. till it grew out into a mullett!! Thank god my hair grows so fast.. but it did take 5 months to grow out!

  20. Kate says:

    Oh God, the biggest hair risk I ever took? In October of my Sophomore year of high school I had this FABULOUS idea of cutting my 2 inches past the shoulder layered hair into a very, very, VERY short layered cut with very short bangs and my dark brown dye accidentally colored my hair medium black! It was absolutely awful.

    My face just can’t pull off short hair well and my fine hair made the cut flat and not fluffy!

    It was kinda inspired off this picture-> http://www.uusikaupunki.fi/~trkakulm/cutout2.gif

    Did I mention it two and a half years to get my hair past my shoulders again? I actually grew out my bangs and the day before my senior year of high school, I got the after-Runway-Makeover Anne Hathaway in “Devil Wears Prada” cut only shorter. Even my senior pictures were out of date by two months as I had no bangs in my pictures. I still have the same cut only the length is a bit longer. I’m very happy with it.

    That experience taught me to not go short. I just can’t pull it off anymore. As a kid, I could because of the baby fat but I can’t pull it off anymore. Short hair A)doesn’t flatter my facial structure and B) does not make me feel confident. I’m a long-haired gal.

  21. Jessica says:

    How ironic you posted this today! Exactly one year ago today I chopped off all of my hair to donate to make a wig for a woman with cancer 🙂 12 inches gone left me with only about 1 inch of hair!

  22. Karen4 says:

    Back in 1987 when I was a manager for a nightclub, I asked my stylist to cut my hair about 2″ long all over a la Madonna (when she was in the blonde bombshell days). That way, I could funk it out. Well, my gabby stylist kept cutting and cutting until I was left with nearly nothing! My hair was about 1/2″ long (think crew cut) with a bit of bang fringe. I was so mad, I never let anyone near me with a camera for almost a year (it took one and a half years to grow it out–my hair grows rather slowly.) Ugh! It was so short, that gel wouldn’t even get it to stick up straight. What a disaster!

  23. Alison says:

    When I was 13 I felt so sick of my long hair one day that I had it all cut off. It was a very short pixie cut and I hated it! I cried for what seems like weeks, there is no photographic evidence and I didn’t go to the hairdressers for about 5 years after this disaster! I couldn’t even face going for a trim. Horrible experience which scarred me for life!

  24. xtina says:

    Biggest risk?
    Chopping off four inches.
    Or possibly getting golden brown highlights in my raven-esque hair.

    I want to perm it soon… 😀

  25. Ann says:

    i’ve been a life long brunette, and last summer decided to have it dyed red wich was a long process of bleaching then laying down the red color….I loved it but found out that red is indeed the color that fades the quickest, and the root upkeep was tedious….now I’m back to brown.

  26. HoneyBrown1976 says:

    I cut my hair really short in a texturized style. I actually liked it. But, I wouldn’t do it again.

  27. Candace says:

    I am currently living with the aftermath of an impulse haircut that I had done two weeks ago. I had a chin-length grown out posh-bob brown with blonde highlights and was on the fence about whether to keep growing it or chop it. Silly me I went for chopping it.
    And I got it bleached blonde, like really platinum blonde. With chunks of color… fuschia pink and purple. The kids in my daughter’s grade one class thought it was cool lol. Now the color is washed out to a pastel-y easter egg color and my roots are screaming out dark browm. I wish I hadn’t done it, the countdown to my next appointment is on… two weeks and counting… Back to a beautiful chocolate brunette and the process of growing it out.

  28. Joanne says:

    I think 2007 was the year I took risks on my hair. I got straight blunt bangs because I liked how it looked on Anne Hathaway in devil wears prada… then after going through with my best friend, I cut my long hair and got a short A-line haircut because I liked Rihanna’s hair. The first cut was bad so I went and got it fixed the 2nd time. It was so horrible trying to maintain it and having only 1 hairstyle. Last January was the last time I cut my hair because this guy messed up big time! I don’t even want to go into details! But I am happy with my hair right now

  29. Joanne says:

    I think 2007 was the year I took risks on my hair. I got straight blunt bangs because I liked how it looked on Anne Hathaway in devil wears prada… then after going through drama with my best friend, I cut my long hair and got a short A-line haircut because I liked Rihanna’s hair. So I know what you mean when you felt liberated after all that hair was gone. The first cut was bad so I went and got it fixed the 2nd time. It was so horrible trying to maintain it and having only 1 hairstyle. Last January was the last time I cut my hair because this guy messed up big time! I don’t even want to go into details! But I am happy with my hair right now

  30. Joanne says:

    Sorry the 2nd one was edited

  31. YL says:

    mine was cutting off my long hair into a short bob three years ago. it was totally an impulse and turned out to be the best decision ever 🙂 i also found my regular hairstylist then and always go back to do my hair with him!

  32. Gloria says:

    I’m very very adventurous with my hair. I figure it grows out, so what’s the risk? To get the point, I had my hair dark plummish red with purple highlights recently, which faded to a nice pink. Then I decided to turn those highlights platinum blonde, but kept some of the pink strands. So now my hair is dark red with blonde, copper, and pink strands all over. That to me is normal.

    So the biggest risk I took was growing it out my 3rd year of college. I had a big dance performance at the end of the year, and it’s for a Chinese cultural dance. So for all the dancers to look cohesive on stage, it was better for me to sport boring black hair. Plus it was easier having it long-ish.

    The week after the performance I went and dyed my hair red again. =P

    Gloria´s last blog post..Bobbi Brown at Fashion Week – Rachel Roy

  33. Redhead says:

    Hmm.. the biggest risk Ive ever took with my hair was when I was prepping my hair for a bat mitzah, and I wet to bed with rollers in my wet hair, took them out in the morning (I had big, FAT, wild waves), straightened my naturally EXTREMELY curly hair and then curled the ends. It turned out to be actually really pretty after I straightened it, but only after I curled the ends did it turn out to be super frizzy ad hideous. I had to douse my hair in cold water and leave it natural.

  34. Rachel says:

    I wear my hair crazy-short, and have for several years, so short cuts don’t scare me. However, last spring, I dyed my mouse-brown hair jet-black with a hot magenta fringe around the face. LOVED it. Most everyone tells me they prefer my hair very dark now – although I didn’t keep the hot pink (too much work).

  35. Amy says:

    I walked into a salon and cut off over 10 inches of my hair for a pixie cut over a year ago. It was really liberating to finally be free of my curly hair, but my family thought it was the result of some sort of emotional trauma. I had just been wanting a pixie cut! I’ve never looked back since.

  36. Brenda says:

    A few years ago I went from hair just below my chest to a Rihanna like bob (Only way I could think to explain it) and I loved it! So little care was required, it was easy and awesome. Sadly my boyfriend does not like short hair and threatens to shave his hair off if I cut mine =(

  37. YouSeeSaf says:

    I have very very curly hair and the last time I’d had it short I was about 8 and my dad had hacked it off himself. I also for some reason thought it looked good brushed out.
    Anyways, last year I took the plunge and got it short again. Think chin length, layered, and shaped around my face. Sort of bob-ish?
    It actually looked really good! It’s a cut that makes the most of my curls cus they don’t need to be tamed.
    I’ve been growing it out since then (last Feb) and I’m getting it cut the same way today at 3:20 🙂

  38. Cathryn says:

    I have always taken a lot of risks with my hair – usually in its cut, not the color. So I’ve practically shaved my head on many ocassions. It makes my family mad because they like my hair long. Naturally my hair is a dark red, and I have very fair skin, so changing the color is usually problematic. I went too burgandy in college and the pictures from my 21st birthday reflect that! I’ve cut it off pixie short several times, the last time being last summer. I’m growing it out from that cut now. Now that I’m getting older (25) I want too grow it out to a litle below shoulder length and then let the natural waves take over. I’m getting lazy.

  39. Glosslizard says:

    When I was about 25, I decided to cut my hair really short, having visions of all those sassy, short-haired Patrick Nagel vixens. Unfortunately, with my fine curls, I ended up looking more like a poodle with bedhead! I let it grow out immediately after getting the cut and I have never looked back! Long waves for me thanks, with my hair type they’re actually lower maintenance than short!

  40. Camille says:

    I’d have to say 3 years ago when I took a pair of scissors and cut all of my relaxer off so I could grow my hair out natural. I did it and it was a shock at first, but I got used to it and now I have shoulder length dreadlocks that are oh so gorgeous.

    I’d do it again tomorrow!

  41. Felis says:

    When I stopped working my horrible college-administration job, I cut my waist-length hair into an asymmetrical bob and dyed it dark emerald green.

    It’s still green and asymmetrical six years later. 🙂

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