Stylish Trail Haircut

I happen to like my hair generally.  I say this because so many women I know do not.  Women with straight hair tend to want it curly and vice versa.  Mine’s on the curly side but not that thick, which makes it malleable.  That’s not to say that I put much effort into it, but it’s easy enough to deal with.  But here’s the thing: my best guess is that it’s going to be more trouble than it’s worth on the trail.  I mean if it’s cold outside and my hair gets wet, it’ll take hours to dry and could affect my core body temperature.  If it’s hot, it’ll get sweaty, which will contribute to the general backslide on the cleanliness scale.  Bugs could certainly get cozy in its shady alcoves.  Worst of all, my hair sheds like crazy, and in fact it does drive me crazy: hair all over my sleeping bag, tent, clothes. Ugh.  I blame my older sister for this distaste of loose long hairs. Let’s just say that we shared a bathroom growing up, and it wasn’t pretty (yeah, I said it, sis.  Now I feel better, and we can move on.).

So the sensible solution would be to cut it all off, right? I mean shorter than I’ve ever had it, like “are you a prepubescent boy” short. But now for the downsides.  I’m not that vain, but I am a little vain.  I mean my sisters have been needling me to pluck/wax my eyebrows for a dozen years, but I’ve held strong.  I figure that if someone is judging me that negatively for the (quite beautiful, if I do say so myself) state of my eyebrows, then I probably don’t need to worry about him/her anyway.  But super short hair might be another story.  See, I have chubby cheeks.  They’re not fat, but I don’t have a strong jaw line.  Combine that with super short hair, and I think we’d be going with the Elmer Fudd look.

Still, I feel like this is the only time in my life that I would be able to do it without getting too many concerned looks and queries about my health.  And it would definitely be a motivator to reach Katahdin: “There is NO WAY I’m leaving this trail until my hair grows to a socially acceptable length!”  I do have a friend’s wedding celebration that I plan to attend a couple of months into my hike, but I suppose, if it matters much to her, I can always put an over-sized bow in my hair like new parents do to their child so that people will know I’m a girl.

I’m still tossing this one back and forth but am seriously leaning on the side of a close crop.  Oh, I know! I’ll let some company shave its logo into the back of my head.  Seems like a small price to pay to motivate someone to sponsor my trip.  It’s just hair after all.


70 thoughts on “Stylish Trail Haircut

  1. Pingback: Labor Day Weekend Hike « My Meandering Trail

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  3. I just cut my hair short, and love it.. if you think you would like to try it, you could go online and look up “ladies short hairstyles” images. when you find one you like, print it and take it to a salon. dangerous to go for a haircut if you leave it in their hands. Good luck, and please post a photo if you do decide to get it cut.

    and thank you for visiting my blog and for the like 🙂

  4. I got a short haircut when I was 12 and haven’t looked back since — and I’m very nearly 30 now. There was a year there when I was just lazy and it grew back to about shoulder length,but in general, I find the right “boy cut” looks just fine on women. I go short enough that they need to take the clippers to my neck, but they’re not needed for the actual cut, which is above-the-ear. I second Vicki’s suggestion of finding a photo you like.

  5. I grew my hair out long for the first time since I was a teen (MANY years ago). Now I wish I’d stayed with long hair all my life. It’s so easy to take care of. It’s hot where I live in the summer, but I pinned it up or wore it in a ponytail. If you keep it long on the trail, you could put on a stocking cap if it gets wet and cold.

  6. The sexiest woman on Star Trek (the TV show) had a shaved head; Sinnead O’Connor knocked me out with her clean head.

    I say “Go for it!”

    …Plus, I’m a Man Of The Future and love the simplicity of washing, etc. Great for the trail, which I’ve done lots of…

    …and thanks for visiting my blog and liking it! 😉

  7. You are on an exciting journey. Thanks for stopping by the Art Prescription. Thought I’d ring in here since I recently on a plain old Wednesday night started to “trim” my hair and ended up cutting it to about 1/2 inch all over!! Yes I have had a few “how’s your health” looks and comments. Also, wow that’s cute, chic. And it has been so freeing!! Best wishes on your trek.

  8. Pingback: Try a New Hairstyle. Hold the Remorse. « My Meandering Trail

  9. My motto has always been “it’s just hair” it will grow back. I’ve been every color of the rainbow (sometimes 3 shades in one night) and every length. If you don’t try it you might always wonder if you’d really like it. There’s always hats and headbands if it doesn’t work out 🙂

  10. Girl:

    I am a “like” my curly hair woman as well. Growing up my mom always kept it really short; upon gaining hair control, I grew it long. In typical college girl self-rebellion, I cut it off. Kept it short for a while, been back to long for 15 years or so. Totally flirting with cutting it short again BUT thinking about going total rockstar and going platnum or something…My point is, DO IT.

    • I don’t suppose you ever were forced to endure the dreaded curly-hair bangs? Or perhaps to brush out your hair into a frizz ball on a daily basis? If so, it sounds like our moms’ techniques were similar.

  11. I have met loads of girls who look hot with short hair. I however, don’t. I got a really short hair cut 4 years ago (like shaved at the sides) and now it is a couple of inches below my shoulders and looks so much better. My lovelife suffered! I would say do it if you like, but have a long consultation with your hairdresser. On the trekking side, I’m currently in South America trekking through all different climates. Hair keeps you warm in the cold, you can put it up to keep cool in the heat and you don’t wash it on treks – usually there are no facilities. You take dry shampoo or go greasy! At the end of the day, it’s a fun dilemma to have though right? Thanks for liking my blog!

  12. Okay, I’m going to weigh in!

    Back story of my hair affair: I am a minimal make-up wearer, jeans or skirt+boots and black turtleneck kind of gal, almost never pluck my eyebrows, eschew nail polish . . . but I LOVE my long, wavy/curly hair. And so does my face – I’m a Dutch/German/Peruvian hybrid, which has blessed me with strong cheekbones and nose, and an oval face. Strong features look best when framed by long hair. A theory I’ve tested three times, always with horrible consequences!

    When I hiked Machu Picchu, I cut off most of my hair for the same reasons you’re thinking about cutting off yours, and YES, it grows back — but it would have been so much easier to just go all Katniss and wear it in a braid!

    • Oh, a braid! That is a good idea! Hm, I’ll have to think about it, though, because then I’d have to deal with washing it and maybe even buying a brush. Maybe I’ll talk to long haired women (or men, I suppose) that have hiked the trail to see what they did.

  13. I wish I was brave enough to cut my hair short! I have long curly hair, and it’s pretty manageable. Sometimes I’d love to cut it all off like some of the adorable short hair styles I see, but I have a round face, and I lose my nerve thinking I’ll look like a fat pale man. *sigh* If you’re brave enough to do it- DO IT(and then post pictures!) 🙂

    BTW- thanks for stopping by my blog 🙂

  14. Lol im the one who straightens my curls so I could grow it a lil … Cept the humidity in Bali was a nightmare so I had it braided with extensions there (super cheap) 😀 … Go short and comfy with minimal fuss when ‘travelling’ 🙂

  15. Watch for short haircuts on strangers and ask them who cut it. Not all hairdressers are equal! I found one I trusted, and now people stop and ask ME who did it! I am 59 now, and have been doing “referrals” for four years. She convinced me to take it off, and go naturally silver and it has been totally liberating.

    • That’s awesome! I hope I’m brave enough to go “au natural” when my hair begins to change colors. In this case, my friend’s sister will be cutting my hair. I have all the faith in the world in her.

  16. You should use one of those apps where you upload a pic & choose various hairstyles to try them out. Of course, it won’t be any fun for us readers of you don’t upload a selection & let us vote for our fave

  17. I walked the 90 mile West Highland Way in Scotland a few years back and one of the first commitments to the walk I made was to go short! I loved it! I found someone whose hair I admired, asked for her stylist and made the appointment. Yes, there were almost a few tears while in the chair (going from a bob to micro-short), but I was over that in minutes 🙂 I’ve just got “family” pressure to let it grow again, but when I’m ready for another long-distance walk it’s outta here. And, I don’t think one’s face shape is a stopper…a good stylist will make it work!

  18. Women look beautiful with no or very short hair. I live in a part of the world where it’s popular…so be fearless and see how beautiful you are without your lovely locks, which will grow back–if you even want them any more. My hair was well below my waist for years before I shaved it off, and oddly enough, more people wanted to touch that buzz than ever did my beautiful strawberry-blond hair. Enjoy the walk, well worth shedding the hair for health and comfort. And think about Sinead O’Connor…she was gorgeous without hair.

    • Lovely locks? Haha, nope. I totally abuse my hair…split ends, dead ends, you name it. Lopping it off will effectively be my one annual haircut, just made extreme.

  19. Pingback: Sisterly Advice: Move on and Leave the Couch « My Meandering Trail

  20. Why don’t you go for a mid-length that you can either tie up or leave loose? I have curly hair too, and went for the short hair deal in a desperate bid for a clean-cut career girl look. I invested in a pair of GHD’s to battle the curls, and kept up with it until I got bored with the girl routine every morning; once a tomboy, always a tomboy in my case. But a tomboy with long hair.

  21. I agree with all the short hair=awesome and hot comments. The good news. It’s just hair, it will grow back. The bad news, as it grows back on the trail it is going to be annoying. You’ll need barrettes and bandanas, etc. to hold it out of your way/eyes because it isn’t long enough to pull back but you’ll need that stuff if you keep it long too. You may find that the short cut comes at the end of the trail when you can’t get the bugs/smoke out of that long hair. (Thanks for liking my blog)

  22. A photo would be great, but even without seeing one, I vote for a cute boy cut! it’s effortless! When you’re cold, you can put on a hat; when you’re hot, you can take it off, when you’re ready to flirt, some lipgloss and mascara will render you smokin’! Go for it!

  23. You have a great excuse to go short,at least you won’t have to faff around with it, just wash and go…if you get a short do just get some sort of sweeping fringe then it will be more flattering on the face…if its a total disaster (which I’m sure it won’t be) and you miss your long hair…there’s always clip in extensions, until it grows back. At the end of the day it’s just hair, so go for it! 🙂 x

  24. I understand your dilemma. Before I ventured out on my 2-year road trip I knew hair care would be problematic. So I cut off more than 12 inches. It left me hair just above the shoulder. It looked cute and was easy to take care of. You need to do what is most comfortable and know it will grow out. Mine is still growing.

  25. I too have hair issues…my hair is thick and wavy/curly. Most times it gets twisted up in a banana clip with the bangs blown out. If I’m feeling super motivated I hook up the curling iron and create “natural” woman made curls in random sizes around my head then finger comb out. I’ve finally just given up trying to change my hair texture and just tell my stylist “hey make it work for what it is”. 🙂

  26. Sounds like your hair is similar to mine, wavy but not too thick so it can be managed. I had short hair for three years and loved it! I think short hair (and pony tails or buns) look best on women because the eyes appear larger and you can see all her features. The only reason I don’t keep my hair short is because it’s very time consuming with many trips to the hairstylist, whereas longer hair I only go every three months or so. Go for it, and let’s see pictures 🙂

  27. My guess is start medium short. A less dramatic start gives you a feel before going way-short. Through hikers all “hitch” into many different types of towns and receive trail-magic along the way. Decide by doing. My wife wanted to cut off all of hers before the journey we now share… but so far, its still long. I shaved mine during her chemo 2 years hair is a fair topic. My friend’s son just completed georgia to Maine. Maybe I’ll ask his opinion and/or send him the link to your blog. I bet he is a slightly different person than when he started. I read his posts and pics the whole way. He really changed the things he carried. (Cut his toothbrush in half, mailed his tent home etc. etc.)

  28. Company logo shaved in is the way to go! Haha (sort of kidding) great blog, excited to follow! If you are interested in mine, I send some great content through my newsletter as well. If you go to my page and click on the “monthly newsletter sign up to stay in touch link” you’re subscribed!

  29. Hi Jordana,
    I don’t know about the possibilities in Virginia, but I had the opportunity to sell my hair. That made the decision a little easier to me. I had a length of about 20 inches and sold around 16 inches for 170$…
    (Btw: I like my hair too, although I’m neither the curly one nor have straight hair – it’s unfortunately somewhere in between)

  30. Pingback: Stylish Trail Haircut – Revisited « My Meandering Trail

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