Embrace Messy Hair

I am not one of those polished and elegant women, who seem to exist only in movies and Copenhagen Cycle Chic.

I range from feeling slightly unkempt to a hot mess, depending on the day and my mood.  This has always been the case, predating my bicycling lifestyle.  For this reason, hair was never a big issue for me when I started biking to work.  My hair is just there, often thrown back in an uninspired ponytail or braid.

After taking off my helmet and walking through the Chicago wind, I usually look something like this:

My motto: embrace messy hair.

You know, I try to be clean and otherwise professional in my appearance, but the world doesn’t point and stare if my hair is not perfectly coiffed.

I don’t think my legal advice is taken less seriously because I may or may not be wearing a scrunchie.  (Okay, I should be really embarrassed by that, but scrunchies are so comfortable.)

{This print from Etsy seller funnelcloud studio via Cup of Jo sums it up perfectly. I need one for myself and extras to hand out and spread the message of liberation.}

Sometimes I do get tired of my boring ponytails and Little House on the Prairie braids, though.  For times when I want to be a bit more stylish – but still in tune with my messy nature – I’m mentally filing away these two super easy “messy” hair styles I came across.

Both of these should be easy enough to throw together in the ladies’ room after jumping off my bike.  And I personally think that women with seemingly effortless hair like this are the most elegant.  Good stuff.

What kind of “hair person” are you?

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39 thoughts on “Embrace Messy Hair

  1. Elisa M says:

    The past few years I have kept it short enough to just run my fingers through after a sweaty summer ride. this year I am growing it out and now sure what that will look like. I am imagining a lot of little barrettes for a thrown together messy look.
    That side pony would be so cute on you!

  2. Miss Sarah says:

    “Messy” hair for me doesn’t look all carefree and unkempt in a pretty way because my hair is so coarse. Bad bad hair for me usually looks like I have escaped an asylum.

    But that’s why I keep it short-ish, in a bob. Then all I need is a bobby pin to either pin my bangs to the side, or back. As long as it’s not in my eyes it’s all the same to me!

    • Dottie says:

      “Escaped an asylum” made me laugh out loud, but you always look so polished. I should have said such women exist only in the movies, CCC and Girls & Bicycles! Your bob is perfect for you hair type and your lifestyle, it seems.

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  4. Thom says:

    Style & confidence seem to always trump
    “perfect” hair. You’re all set!

  5. Steve A says:

    “I am not one of those polished and elegant women…”


    Seriously, I’d be happy to have messy hair, or any other kind of hair…

    • Accordion says:

      I have long thick wavy hair plus a fringe. Ponytail under the helmet, release at work then a hair clip to look pretty. Mini-straightener at work for emergency fringe fixes (in the toiletries bag along with the “other” spares). My commute is too far & hot to wear work clothes.

  6. My hair is naturally curly and unruly, so I usually try to straighten it, so that it doesn’t get tangled on me. Failing that, I pile it up into a bun and secure using a clip. But I don’t look nearly as chic doing that as those girls in the “sexy messy” photos.

  7. April says:

    I have long thick straight hair–just down to my waist if I wear it down. I also have bangs.

    I am strictly wash-and-wear. I don’t even own a hair dryer.

    Most of the time my hair is braided in one or two braids to keep it off my face.

    I’ve tried wearing it down more, but it just gets tangled and breaks!

    I find long hair so much easier to care for than short. I only have to wash it twice a week, tops (for some reason, short hair seems to get greasy faster, maybe because it touches my face more? I wash my bangs every day), and I can pull it back into a braid or two and it’s out of my way and off my face.

  8. Sigrid says:

    When my hair was shorter, I had to straighten it, now that is longer, I love letting it be. Running my fingers through to dry and finding many a bobby pin as my friend in numerous helmet-head instances. Just today I tried my first braid ~ finally, getting long enough to have more fun. This post is good stuff indeed, especially as Spring approaches. Thanks!

  9. Short, short, short. I have worn short hair for years for the convenience of it and When I started riding bikes I found the transition easy. Shoot, I have days I don’t even run a brush through it, my fingers work the best!

  10. I like helmet hair on bike women. I think it looks wonderful and alluring. Embrace messy hair indeed!

  11. Kara says:

    I have been really getting into braids lately. I am terrible at braiding my own hair, but I love the look of a messy braid. I even have gone as far as doing the “Heidi” look with the braids on top of my head. But that is not very compatible to wearing helmets.

    I also just discovered a way to turn my straight hair curly without any heat. So I am playing around with that for sure.

    Love these looks you posted, Dottie!

  12. Maureen says:

    Helmet hair is a problem for me. I have thick, shoulder length hair which seems to enlarge with humidity or totally flatten with my helmet. I wish I had your confidence. I do think of cutting it a bit shorter.

  13. Dave says:

    I actually wear a hat partly because if I don’t, I get to work in the morning looking like I went through a wind tunnel on my way in. The hat keeps my hair flat. Thankfully in the summer here it isn’t hot enough in the mornings for me to get sweaty, but I definitely do on the way home. Nice thing is, the same hat keeps my head, face and ears from getting sunburned. Multi-purpose!

  14. SM says:

    Funny how I was thinking about this yesterday – messy hair – with 30 mph winds blowing tree branches and other brush all over the place (not a great day for cycling btw). My hair is naturally wavy and always has that messy look. I try to flat iron to give it that coifed look for the office once in a while, but I too embrace the messy look. For cycling: depends – pulled back some how if wearing a helmet, if not, anything goes.

  15. Amy says:

    I’m also a wash and go gal. Actually, I’m a wash the night before, forget to brush it before I head out in the morning and then run my fingers through it at work since I don’t carry a hairbrush and hope I don’t look too mad. Today I’m sporting the haven’t even washed it or brushed it and have it tied up somehow just so it stays out of my face look. :)

  16. beany says:

    Hi, I’m a scrunchie user and proud to be one.

    I finally got layers to I can wear cutesy little buns and pretend it looks chic and elegant. I can never let my hair down completely because I almost inevitably wind up looking like Slash or the Thing. So it’s always put into a pony or a braid.

  17. Dottie, both you and Tricia seemed to blessed with very good hair and carry off messy quite well. I’ve had life long issues with my hair, which is as fine and thin as a 2 year olds. My hair is always cut in a carefully layered bob. That’s really about all I can do with it. I love the messy, wind-swept, romantic look but it just doesn’t have the same effect with baby-fine hair. If I lived in a humid climate I would never, ever wear a hat or a helmet when riding my bikes because my hair would be a complete sweaty mess, requiring a shower and blow dry. Luckily, in arid Flagstaff I just don’t get that sweaty on a bike ride so my hair is able to withstand the helmet.

  18. Coreen says:

    One of my greatest joys in life is the wind in my hair. It’s still too cold here right now to set it free, and it has to hide under hats and hoods and scarves, with any escaped strands getting iced up with sublimated breath. Either way, my hair’s always on the brink of chaos.

    • donna says:

      I too have tried to be more relaxed about my hair since I took up biking to work and wearing a bike helmet. But by relaxed I mean by not caring too much about how it looks when I get to the office. I still spend a lot of money highlighting my thin, wavy long hair and buying stuff in the hope it will magically turn thicker. I try not to blow dry the hell out of it and that has helped a lot. And trying to limit products with silicones. I love the two styles you posted btw.

  19. So sorry, but I find you terribly elegant and charming, Mrs Dottie! ;-)

  20. Holly says:

    What kind of “hair person” are you?

    I’m pretty certain that last week my hairdo was a cross between Simon Lebon and Phyllis Diller.

    I wear a shortish, shaggy ‘do that’s very layered. I forget to get it cut for months. Everything’s going great and then one day, it just goes insane and I can’t wait to get in for an appointment. When I finally do, THAT is the day my hair looks “normal” again.

    I second your encouragement to embrace messy hair. You kinda have to relax the idea of perfect hair if you’re riding a bike. That’s a fair trade-off as far as I’m concerned.

  21. * says:

    Plse look into your email. ;)

  22. Super polished hair often looks dated to me. Unless it’s crazily stylized and deliberate, at which point it starts looking cool again on the right kind of committed person.

    I don’t have any complaints about my hair so I will wait for the posts about other features :)

  23. Courtney says:

    ha! i am also a bike rider in chicago, and my boyfriend and i often ride together. he always thinks it’s hilarious to see how crazy my hair looks after riding around in the wind.

  24. Anne Hawley says:

    I decided about a year ago to cut it all off. My hair is about an inch long. A little product and off I go. Helmet hair? Not a problem! I just run damp hands over it and force it back into position.

    It’s AWESOME! But not, I understand, the way for everyone.

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  26. Nicole says:

    Mine is always messy, I guess. So is my bf’s, but I like it that way :D

  27. wwbpa says:

    I’m part of a NJ bicycle and pedestrian advocacy group and am working on a post for our website about fashionable helmets (having just come across a company at the NJ bike summit that makes them). Do any of you have any recommendations?

  28. Mandy says:

    I’m a bit late to the game here but wholeheartedly endorse the embracing of messy hair. My best friend actually drew me a picture as a gift with the caption: “Beware of perfectly coiffed hair.” My strategy is the “messy updo” using a handful of those 1-inch claw clips. With a bit of practice it takes about 30 seconds, comes out different every time, and is actually enhanced by hair being somewhat windblown.

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