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The Thirty-Day Challenge That Taught a Hair-Down Girl to Love Updos

From bobby pins to relationships, one woman shares how wearing her hair up revealed a lot more than her neck.
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Photo Credit: Anne Marie

Long, tousled locks are my specialty. Equipped with my ever-faithful round brush and blow-dryer, I am content to live my life hair down and blowing in the wind. Aside from the necessary ponytail when I’m working up a sweat, I don’t do updos.

At least, up until now.

In contrast to the mussed-up tresses of J.Crew, Madewell, and high-fashion runway models—for whom the lines between effortless and can’t-be-bothered-to-give-a-crap are so very stylishly blurred—something about arranging your hair always seemed a little too punctilious for me.

But this summer, my understanding of beauty has been challenged and my hairdo M.O. tested. My boyfriend, ever affirming of my sense of style and always sweetly appreciative of my head of hair, got curious, you see. After a few encouraging compliments when he would spot me with a sweaty ponytail at the gym and questions such as “Why don’t you ever wear your hair up?” I got the hint.

It was inevitable, I suppose. You can only know someone so long before you begin to wonder what their ears look like. So I was faced with a classic female beauty dilemma: Do I set aside my staunch anti-updo attitude to try a few styles, or do I tell my boyfriend he can “like it or leave it”?

As a way of letting my man know he matters, I figured I would give some updos a shot. And because I am an editor of a women’s magazine, I decided to make it a challenge—I would do it for thirty days straight and chronicle the process. Here’s what I learned.

01. Do a test run.

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Photo Credit: Anne Marie

If you have spent as much time as I have in the black hole of hair tutorials online, you can attest to the fact that all the promises of it being “quick and easy” lure you into a false sense of confidence. What became clear to me is that yes, a particular updo can be easy to pull together—if you have practiced it several times beforehand, that is. I can’t tell you how many times I was rushing to get out the door in the morning, only to realize that the updo I had planned for the day was just not working. Save yourself the stress, and practice your updo a few times before it makes its debut. Your trial run will open your eyes to best practices. Oh, and if there’s not a how-to video, there’s probably a reason (read: It’s not for amateurs).

02. Your hair is not long.

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Photo Credit: Anne Marie

At the time of my updo bonanza, my hair reached to the middle of my back, just past my shoulder blades. This, I thought, was long. But trying to wear my hair up every day taught me otherwise. Unless your hair is down to your bum, you do not have long hair. I was naturally drawn to beautiful braided concoctions, but I soon learned that all that winding, twisting, and crisscrossing left me with a very unsatisfying end result. Unless you are willing to grow your hair out past your waist or get extensions, your braid will not look like Princess Elsa’s. I’m sorry.

03. Not all bobby pins are created equal.

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Photo Credit: Anne Marie

There is nothing more frustrating than finally finishing a lovely braided crown, only to realize that you have bobby pins sticking up all over the place—or worse, your carefully formed bun slowly slips out throughout the day. As I learned the hard way, your typical pack of Goody bobby pins are for amateurs—Japanese patented technology bobby pins are really where it’s at. A good bobby pin means fewer pins in your hair, and, therefore, a superior hold with each pin and less headache at the end of the day. It would be worth your while to invest in better bobby pins. Trust me.

04. Your hair texture matters.

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Photo Credit: Anne Marie

Captivated by Zoe Saldana’s famous “sidewinder” red-carpet updo, I set out to recreate this look. With no how-to of any kind and no practice beforehand, this look was a total flop. As I assessed what looked like a side chignon that had been mauled by a wild beast, I realized that a big part of my problem was that I have fine, relatively silky white-girl hair, and Zoe’s hair texture is fabulously different. What works for Zoe’s thicker, kinkier hair type will not work for me. And that’s OK. In the same way that we must discern which fashion trends complement our unique shape and size, so must we take a critical eye to updo looks. Ask yourself if a certain style works with your face shape or hair texture before you attempt the updo, and be open to the answer being “no.”

05. Your hair is an Ouchless Clear Elastic graveyard.

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Photo Credit: Anne Marie

I have three words for you when it comes to updos that involve those handy clear mini elastics: Cut. it. out. I don’t consider myself a super penny-pincher when it comes to beauty supplies, but for some reason I resisted the idea that these little rubber bands might have a one-time-use life expectancy. But, after demolition of my super-fun fauxhawk updo, I learned my lesson. In an attempt to avoid the pain and loss of hair when it came time for me to undo my pull-through braided bun, I just snipped those bad boys out, and let me tell you, it was so worth it.

06. Embrace the unexpected.

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Photo Credit: Anne Marie

As it is with your everyday “downdo,” so it is with your favorite updo. Most updos you fall in love with will not look the same as the tutorial, and they won’t look the same the second or third time you wear them either. Every single one of the updos I tried never looked exactly like the style I was attempting, and most of the time that worked just fine (but sometimes not). In fact, some of my favorite hairstyles were of my own making (like when I decided to wear three little mini buns in a row). Enjoy the fact that the hairstyle idea you borrowed from the Internet is a new creation when it’s in your hands.

updos for long hair, updos for short hair, easy hairstyles

Photo Credit: Anne Marie

After a month of updo trial and error, it turns out that I was just as right about my preconceptions as I was wrong. Updos do take care and a good deal of fussing, as even the most “effortless” varieties require some fluffing and arranging. I found that even amidst the do-overs and subsequent stream of choice expletives, the time I spent fixing my hair just right—or attempting to—was an act of thoughtfulness. Unlike the “this is just how I came” spirit of effortlessly tousled hair, updos are decidedly spruced up. I found that they served as a kind of compliment to others—it communicated to those around me that they were important enough for me to make a little special effort to impress.

And it turns out that I actually like putting my hair up from time to time. I loved imitating my favorite look from that romantic last scene of Gwyneth Paltrow’s Emma, finally trying those Heidi braids that I never thought I could pull off and discovering how casual yet elegant a low chignon can really be. I also came to see how well an updo can complement the right outfit or add a little funk to a boring black T-shirt and jeans combo. A few buns, braids, and twists in your repertoire can be accessories that will add some spice to your entire look.

Yes, I still do love my hair down (and my boyfriend does too!), but I’m excited to try some new updo styles. Even better, I have a few pretty little tricks to pull out for those moments when I want people to know that I do, in fact, give a crap.

Ill be sharing some of my favorite looksand the tutorials to try yourselfhere soon, so stay tuned!