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

Published in: Hair, Just For Fun

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

I ask this one every so often, but mine was right after a bad breakup. I was half out of my mind with heartbreak and looking for a fresh start with a new look, so I asked my stylist for help.


I had her chop my long black hair, which was down to my elbows, into a chin-length layered style with the ends flipped out.

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

I remember how liberating it felt to transform my look… Letting go of all that hair was like unloading the baggage of my failed relationship.

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

What’s the biggest gamble you ever took with your hair? Let me know in the comments, and try your luck with the Makeup and Beauty Blog slot machine at the top of this post (if you’re reading this in the feed, click here to play).

Happy hump day!

Your friendly neighborhood beauty addict,



Like this post? Tell your friends!

So far, 42 people have commented on this article. How cool is that?

  1. Andree says:

    The biggest hair gamble I ever took was getting my hair cut while trekking through Europe. I was in Barcelona and desperately in need of a cut — and I spoke very little Spanish. I saw a girl whose cut I liked, pointed to her hair, and asked her “donde?” (“where?”) She told me the name of the place and the name of her stylist. I went to that salon, and he was wonderful. He tore down the language barrier by holding a mirror to my face and drawing on the mirror with a grease pencil to show me what he was going to do. In the end, I loved the style!
    .-= Andree’s last blog post… Review of The Little Giant of Aberdeen County =-.

  2. Tiffany says:

    Hey girlie! Happy hump day fo sho!

    I feel like mine was actually going back to my natural color. In high school I started getting blonde highlights and over time this turned into dying all my all very light blonde. One day I decided I was over it, went to the salon, and asked that they bring my back to my natural color so I could grow it out and hopefully not have to color anymore. They colorist was kinda freaking out, worried that I wouldn’t like it because it was going from so light to so much darker. But I loved it! It was a huge change!

  3. Michelle says:

    Right after I was married I decided I wanted to cut my long hair to collar bone length and get a new color. My dark brown long hair ended up being cut above my shoulder with a purple-y red color. I’m sure my husband was like “what happened to my wife”??? LOL

  4. JC says:

    Right after my Mom passed away, a few days after the funeral I just couldn’t deal with the cute Halle Berry cut I had…so I asked my then bf to shave it off. Think Amber Rose. That was ten years ago. This year I decided to let it grow out.

    I think I look better with no hair, but I need a change so well will see.

    Most admit that the shorter hair is a complete confidence booster.

  5. knownever says:

    shaving my head was a gamble that’s stuck for seven years
    .-= knownever’s last blog post… A Major Gripe =-.

  6. Marie says:

    The biggest gamble for me was a few years back when I decided to get a bunch of cool choppy layers in my hair. But they didn’t look cool, my hair ended up looking almost like a mullet, it was terrible.

  7. Vanessa C. says:

    Hair extensions. My hair has never been the same. πŸ™

  8. BeckBeck says:

    Background: my mom’s original career was as a hairdresser, so until I moved out of state haircuts were free and almost instantly accessible.

    The summer after I graduated from high school I was bored out of my mind, and I wandered downstairs one night and said to my mom, “What would you think if we did something different with my hair?” I’d worn it long (to the bottom of my shoulder blades), straight, and essentially untouched for a solid five years. My mom LEAPED out of her chair and said “Go find the hair scissors, I’ve got half an hour before I need to go get your brother!” She cut my hair into a swingy chin-length bob, and I haven’t worn it long since. πŸ™‚

  9. Hyzenthlay says:

    Cut it into a pixie from longer than shoulder-length. A few months later I let my hairdresser do whatever he wanted with it, so long as he didn’t charge me for it. I ended up with a totally bleached pixie cut. The cut was perfect for me at the time, but not the color.

  10. Rae says:

    I don’t care what you say about feeling awkward with your hair; I’ve always loved yours! You simply have great hair, girl, be it long or short πŸ˜›

    My biggest hair change? Going from loooong (it touched the top of my bum!) to very short — just above my shoulders. It was a *lot* of hair, but I needed a change and wanted to be able to donate it! I changed it up further a little while afterwards by getting red hilights and tips (lots of red hilights in the bottom 2″, essentially,) and then going in AGAIN to have black lowlights put in!

    After seeing the photos from the Chanel show, I’m feeling the need for another hair change πŸ˜› One involving platinum grey-blue hilights, perhaps?
    .-= Rae’s last blog post… The Grammys happened. These looks did not. =-.

  11. amy says:

    First really big change was when I was 16 I decided I want short hair, while having long hair most of my life and the trend was short layered bobs then. At that time, my hair was right above my boob. I cut my hair in a chin length bob with face framing layers. After a few months, I cut it even shorter because the bob wasn’t short enough. I had it cut into a Trish Goth (model) wedge bob cut. I liked it at first but my neck felt very naked. After that I started to grow my hair long again because I missed my long hair. I also had a hard and terrible time growing out my hair. It took two years to grow it long again.

    About 6 years later, I had bleach blond streaks which I kept going for 2-3 years, I don’t remember anything traumatic happening to me though. I think I just really wanted to try being a blond for a while, and was bored of my own hair. so my stylist bleached my hair for a while. I long the lightest of it but the up keep was horrendous. I was in 3 and 4 year university at the time and did not have the money or time for the up keep so I would have black roots for 6 months before I make a trip to the salon.
    .-= amy’s last blog post… MAC Lillyland Cremeblend Blush Joie-de-Vivre Product Picture, Review and Swatch =-.

  12. Indoorkitty says:

    Chopped off 8 inches on a whim with a new hair stylist. I told him, I’m thinking of going short. He dramatically grabbed his scissors and swished them through my hair before I could say another word. It was over so fast! Then he touched it up into a chin length bob and although no one could recognize me for a week, it felt really good and freeing.

    Downside: I didn’t realize until that December that my hair had served as an extra head blanket; it was a cold cold winter…

  13. Sherri says:

    Shaved all my hair off.
    .-= Sherri’s last blog post… Lots of Goodies =-.

  14. Amanda says:

    I have crazy curly hair. The biggest jump I ever made was from mid-back length curls to shaved. Like, shaved with a Bic razor. Yep, I’m that girl!! LOL It was the most liberating, amazing feeling ever. I let it grow out to a short crew cut and kept it that length for about 5 years. Luckily I have a well shaped head with only a few scars (motorcycle accident anyone?). My face looks good with a bald head as well πŸ™‚

  15. I dyed my hair a deep magenta once! I adored it and it was really fun for a short time. I wouldn’ t want that permanently of course, but I still smile when I see pictures from that time.

    I am in ened of some drastic change. I want bangs that fade away into angles, and I too am inspired by the Chanel show. I think I would do blonde streaks though, not grey. I have very light honey brown hair. What do you think?
    .-= Never Enough Nails’s last blog post… China Glaze Up and Away GIVEAWAY!!!! =-.

  16. Kasey says:

    What haven’t I done? In college I cut all the relaxer off and work a short curly natural that was huge, and throughout college it was several lengths mostly short and 1.5 million diffrent reds, and even a horrible blonde 😐 .
    .-= Kasey’s last blog post… Contest Alert: Orient Automatic Watch =-.

  17. Kelly says:

    I have taken a million gambles with my hair in the past actually. I think the biggest was when I dyed it deep chocolate brown about 5 years ago. I liked it, but it started to fade pretty quickly and then I didn’t like it. So 8 weeks later I was blond again! πŸ™‚
    .-= Kelly’s last blog post… Sephora by OPI Nail Colour for Spring 2010 Swatches & Review =-.

  18. Felis says:

    Bleaching my black hair blonde and then dyeing it green four years ago. It’s been green or blue ever since. I love it love it LOVE it. Touching up my roots is a pain, but it’s so worth it!

  19. Tavia says:

    I had long hair, I mean really long and one day I just to my hairstylist and cut it….very very short, like a boy πŸ™‚
    .-= Tavia’s last blog post… Update: ORLY Sweet Spring II 2010 Collection Γ’β‚¬β€œ Swatches + New Spring Lipgloss Swatches =-.

  20. Katie says:

    I know this is really lame, but I was watching Gilligan’s Island, and I thought Ginger was so adorable, that I wanted to dye my hair like her. Soo..I dyed it vibrant red. It actually looked really good, it just wasn’t “me.” My hair is meant to be black, it’s what looks best πŸ˜€

  21. Christy says:

    The biggest change was when I was around 12 years old. I had really frizzy permed long black hair. I loped it off down to above my shoulders. I really needed it, my hair was so unhealthy looking. More recently, about 2 years ago, I got my stylist to put in blonde highlights and change my base color to a medium brown. (My hair is naturally black/dark brown) I love it, but for winter I go without the highlights and just change the base color. I will be getting my highlights back in a month or two. πŸ™‚
    .-= Christy’s last blog post… MAC Studio Fix Lash Mascara Review =-.

  22. Saku says:

    A crazy gamble, I wasn’t pleased with the color. I was in high school and one time I actually color my hair 4 time in less less than two weeks. I know, it was bad on my hair and scalp and boy did I pay for it. I also twice cut all of my hair almost to a shaven point, because I was sick of my relaxed and damage hair. Now I’m naturally curly and like it.

  23. Rosemary says:

    My biggest gamble was too after a bad breakup. I had never had short hair, it’s always been below my shoulders or longer. My bf at the time didn’t like short or dark hair so when we broke up, I was so upset and went to have my hair cut into a bob and dyed it black. Turns out, it was the best looking hairstyle I ever had, except I went to a cheap hair salon right before closing so the stylist didn’t even it out. I ultimately went to my favorite stylist and had her fix it, but it was amazing after that….

  24. Sarah says:

    I thought I could pull off the Beyonce blonde. I did that many years ago but when I look at the pictures I’m horrified no one told me how awful I looked
    .-= Sarah’s last blog post… Beauty Review: St. Ives Apricot Scrub Blemish & Blackhead Control Scrub =-.

  25. NINA says:

    I have always had long hair ever since my mom let me grow it long (ie, she knew i was responsible enough, and maybe vain enough) to keep it clean and combed.

    2 years ago, I had my stylist cut it short, really, really short. I did like it. Took 2 years to grow back. Short hair is easy and tough at the same time – easy to dry but a bit more challenging to style.

    At the start of this year, I had my hair cut chin length – it was down my back already and had not been cut in more than a year. I think chin length is my length. πŸ™‚

  26. RZ Sokol says:

    cutting my long black indian hair shooorrrrt to my ears on a whim. I cannot even tell you how ugly I looked… just to give you an idea, the term “plucked chicken” comes to mind. It took ages to grow back. The thing is, some women look hella fierrce with short hair, but not me though!!

  27. Nina says:

    i recently chopped off my waist length hair to an inch below my shoulders. i love it.

  28. Jen says:

    My hair was a little past shoulder length, and I went to the hair styling school (they were students!) and I had them cut my hair really really really short. Like, boy cut short. However, the student didn’t really know what she was doing, so the instructor did most of the work. I got a professional hair cut for like $6! It came out really nice too! I liked it, but I don’t think I’ll ever cut it that short again. I’m really bad about getting my hair trimmed every 6 weeks though, so growing it back out was a pain in the butt, big time.

  29. YadiQ says:

    i recently told my stylist at bumble and bumble to do whatever he wanted
    lord knows he cut off way more than i anticipated but my hair is healthy and it works lovely

  30. Stacie says:

    I tried to dye my chocolate brown hair vibrant red using an at-home color kit. Maroon, anyone? *shudders* Some girls can totally pull that look off (my best friend is one of them), but not me. I went to a salon to try and salvage it (which didn’t happen, by the way), and the stylist even said, “It’s a pretty color by itself, but it doesn’t look very good on you.” Can’t fault her for the truth–I avoided mirrors for weeks, until it faded! (I actually washed my hair with Dawn dish soap to hasten the fading process! At the stylist’s suggestion!)

  31. Nicole says:

    I agree with Rae–your hair always looks gorgeous. Mine on the other hand…let’s not get into that. XD The biggest gamble I ever took was two months ago when I bleached most of my bangs and left some of natural (dark brown) hair color, like a few strands. Then I dyed it with the Manic Panic “Wildfire”, a bright bright red. Surprisingly, it turned out great! I got a lot of compliments, but none from my mother. XD

  32. Krystal says:

    I, too, have long, black hair and one year, when it was almost down to my hips, I chopped it into a blunt cut a couple inches below my ears. I absolutely loved it, but I agree that the in-between stage when it starts growing out again is a pain in the butt.

  33. Rebecca says:

    I’m pretty much a wimp when it comes to my hair, so I’ve never made any huge changes. I guess the biggest change I made was last summer, when I cut 12″ of it off, so it went from being near my elbows to just below my ears. Having it short is SO much more practical, but I miss my old hair πŸ™ So I’m letting it grow out again. Sadly, I’ve discovered that it grows at a rate of about 2 inches per year. So… ask me again six years from now ;P
    .-= Rebecca’s last blog post… Frederic Fekkai: making the world more brilliant, one hair at a time =-.

  34. diane says:

    I had red bob cut hair and I wanted to be a blond. I went to the saloon and came out a blond. Can you imagine what my hair went through? But it’s still alive!!

    .-= diane’s last blog post… Why do we hate the 90s fashion? =-.

  35. Trude says:

    I didn’t think about it at the time, but looking back I realize what a gamble I took dying my own hair in college! I’m a natural strawberry blonde (my hair was basically orange as a kid, then lightened up when we moved to SoCal), and I dyed it a fairly dark, brilliant red out of the box. It was a shocker at school the next day, to say the least! I hardly thought twice about it, but yeah….luckily for people who met me after, it seemed perfectly natural, but I eventually had to start getting it done professionally because my roots growing out looked so light they were almost gray! I was a redhead of varying shades for about 4 years and loved it, I think it made me appreciate my natural color more. Plus now it’s much less $$ and hassle to go au naturale! πŸ˜‰
    .-= Trude’s last blog post… Caroline & Nancy =-.

  36. Sakura says:

    Long locks to short bob–> Freshman year of college-I decided that I couldn’t deal with my past shoulder length locks anymore. Much to my hall mates chagrin I cut it off to a bob! Ever since my hair has been short. Now more angular…Not having to spent too much time on my wavy (in not a nice way) hair has been so liberating! My philosophy is try it, it will grow if you don’t like it, don’t worry!

  37. Jessica Lynn says:

    After a bad breakup two years ago, I cut my hair that I could literally sit on to above my shoulders! Man, was that scary. And tomorrow I am putting a body wave into my pin straight hair..also scary! I hope it looks like yours πŸ™‚ Your curls are always pretty

  38. ninna says:

    My hair was blonde, long and luscious just below my breasts.
    I was a hairmodel for my boss (I was an apprentice hairdresser) and they dyed my hair a watery red with a bold white streak in the bangs. My bangs were cut assymetrical – half of it was hairline short and the other was cut a little above my eyebrow . They then layered my hair with scissors (which was really painful!) slicing it from the base of my skull, until the longest ends were spiderweb thin and the rest was bob short (and really chunky!)

    It was the worst time of my life surviving this cut and growing it out! DON’T be a hairmodel!

Leave a Reply

Your email address will not be published. Required fields are marked *

CommentLuv badge