The Headband is Back

But can we make it look cool?


I’ve never once looked in the mirror and thought, You know what would make this outfit better? A headband.

It’s the accessory equivalent of that friend we all have who’s super nice and fun and sweet, but for whatever reason is never part of the group. She’s invited to birthday parties — “Hey! You know who we haven’t seen in a while? Becky. Invite Becky!” — and though you wouldn’t text her to hang out one on one, you’re happy to see her if she randomly shows up. “She’s so nice,” you think to yourself. “I wonder why we don’t hang out more often.”

I consistently find myself lingering by the tortoise-shell accessories section of J. Crew near the cash registers, rubbing my thumb over the black and brown mottled plastic hair-things while considering how I’d look with my hair pushed back. But then just as I remember Becky’s voice grows shrill and annoying with each glass of wine she consumes, I’m reminded that headbands offer a specific kind of headache, one that’s exclusive to having both sides of your scalp pressed in by a plastic torture device.

Right. So this is why we don’t hang out with Becky more often.

Save for Blair Waldorf in 2007, a strong case hasn’t really been made for the headband for quite some time. But then just last night Lupita Nyong’o dropped jaws at the Oscars with a simple gold band. The woman is a goddess so she wore hers less like an accessory and more like a crown, but it called to mind the fact that just a few weeks ago headbands popped up on the runways at Helmut Lang, MBMJ, Dolce & Gabbana and Marc Jacobs.


So even if they were never “around” enough to be noticeably gone, they’re clearly coming back. The question is, can your average headed-human make them look cool?

Leandra, Charlotte and I tried it out. Our model was a rose gold headband by headwear extraordinaire Eugenia Kim, embellished with pearls and flourished with a spiky garland, just funky enough that we’d be remiss if we didn’t at least try.

Leandra went first with her pea-head and denim dress — legs covered in leather to add false warmth and extra edge. Charlotte was next, punking up the sweetness of it all with a plaid suit, a vintage tee, and what else but…more plaid. I went last, figuring that if I just really went for it (it meaning a Blair Waldorf headband salad in my ODLR jacket, J. Crew shirt plus boyfriend jeans) I’d look unlike myself but at least like I belonged to the thing upon my head.

I did not. At no fault whatsoever of the headband itself, I looked like I’d been stuck at the bar — alone and for too long — with Becky.

Since this is an experiment in style more than it is a declaration of trend, what do you think: can a headband off the runways or divorced from Lupita Nyong’o’s perfect face ever look cool? And as for Charlotte and Leandra’s attempts, you guys tell me.

Get more Shopping ?
  • I was super into headbands around the time that Carolyn Bessette rocked them effortlessly during her 90s minimalism fantasticness. However, I also got the dreaded headache you mention and found that my face is not nearly perfect enough for them. I always envy them on others, however, and Lupita looked PERFECT, but they’re, sadly, just not for me. The only plus is that, after several attempts, I feel pretty certain about what works for me and what, decidedly, does not.

  • Christina Quinn

    Funny you should mention Gossip Girl, because I think that Blake Lively achieved a highly-perfect perfect Greek-goddessy headband look in Season 2, Episode 1 ( I’m a fan of the headband…but admittedly I also endorse the look of hair bows past the age of 23 and am unabashedly fond of tortoiseshell. The headache though is no joke – they’re not for the faint of heart.

  • FashionKiller

    Is Blair Waldorf making an appearance anytime soon?
    Queen B of Headbands.

    XO XO


  • If I wear anything in my hair, it tends to be a ribbon that I tie into a bow at the top of my head. I’ve always felt that I look awkward in headbands, but there really are a lot of great ones!

    All three of you look striking, which is entirely usual given you guys are you. It seems like talented females who are also good looking are drawn towards working for MR.

    Also, Charlotte, who are those shoes by? They look similar to those Stella McCartney ones!

    • Charlotte Fassler

      Zara!!! I went in there to buy a scarf on a cold day and left with those haha

      • Hahah I was gonna guess Zara. Ahhh, they’re brilliant. And I guess and sort of in the same genre of cold-defiance in that they would keep you a few inches above the snow.

  • I’ve always liked the idea of a headband but also for the reason you mentioned (blinding headaches) don’t really wear them. sometimes when I’m working out I’ll pull my bangs back with one. It’s pointless for me though I usually take them off after about 5 minutes.


  • Cady, will you please tell him his hair looks sexy pushed back.

  • Angel

    Headbands and Headscarf’s are essential in my wardrobe . They are timeless and you can dress them up and down.
    Check out my fashion blog. NEW posts every Sunday , Tuesday , Thursday and Saturdays .

  • Addison Joel Butler

    I’m going to start wearing headbands now. Is that socially acceptable for a male?

    • chatNoir


      post a pic, pleez !

    • Amelia Diamond

      DO IT!

  • leonorjr

    you are adorbs. I hate the headband headache, but love the headband. what is a girl to do?!

  • Aubrey Green

    Can’t get over how amazing her complexion looked in that dress – gorgeous!

    Ya’ll are gorgeous too, your hair looks amazing.

  • Emma

    Lupita Nyong’o is so, so gorgeous that frankly, she could wear a banana skin as a headpiece and still look like a goddess!

  • I’m not saying it’s childish but its childish. Let some trend rest in peace at Walmart in some 2nd grader’s shopping cart.

  • Jen

    I love the idea of them, but I only toss one on when I’m having a very girly or confident day, as I often feel like people judge me when I’m wearing one. In a, “does she think she’s still in junior high” way. I own two – a Joe Fresh leather one with a black bow and a gold sparkly J Crew one. Now I’m inspired to wear one tomorrow! Thanks!

  • check for some wonderful one at

  • Cherie

    Live for headbands!

  • thechicndamned

    I think we should just all skip the headband and just all rock tiaras. x

    the chic & damned

  • Jessica

    Ahhh love these

  • Sienna Miller though..

  • Finally! YAY!!!

  • Kori G

    While I like the idea of the headband, I just can’t really think of a time outside of the Blair Waldorf realm where they really work. Don’t get me wrong, I think that Lupita looked incredible in her blue Prada dress, but I personally thought that the headband took away from her look a little bit. She is a thirty-one year old woman, and her choice in this particular accessory made her look far, far younger.

    I’m torn.

  • Lilli

    I used to have this black plastic headband that would dig so hard into the bit behind my ears I would have the worrrssstt headache!

  • Lilli

    Judging by Leandra in these pics, gladiator sandals are also back!!!!!

  • Ava Maria Arias

    the headband in the main picture looks terrible ? not great at all …

  • The Fashion Brook

    I love headbands! So…great!

  • I think if it’s a simple and minimalist or edgy and cool one, why not? I retired all mine to a box years back when I switched from contacts to full-time glasses. You wanna talk about a headache? That’s pretty much a match made in Excedrin hell. Although with my recently shorn head, I might be inspired to give it another shot… Lupita looks stunning!

  • Hi Amelia, 🙂

    I can’t see why not! As men repellers, we should feel free to try whatever accessory we feel like, and I actually think it looks good on you. However, the best combo was probably Charlotte’s, as her outfit was definitely the most men repelling, so the headband wouldn’t make it any sweet or girly. You must try again with a different outfit! 🙂

    thanks for sharing, lovely post,


  • Christina Gomes

    I never stopped wearing them 😀 I have curly short hair so I think it looks good and not to “in your face”. And I’m also familiar with the dreaded headache, just a matter of finding a model that isn’t too tight! 🙂

  • Katherin Sanders

    Try to wear the headband so that it pinches your head just behind your temples rather than directly on them. In other words, don’t place the ends of the headband just behind your ears. There’s an artery right there – of course you’re going to get a headache! If you can make the headband pinch the bone of your skull instead, you should be able to last a few hours longer. I speak from my experience wearing the cheap plastic headbands you can buy at Target. They’re the equivalent of bobby pins when my hair looks wispy in a top knot!

  • Ranim Elborai

    I used to wear them as a child without complaint, but as my head grew larger with age, they’ve become too uncomfortable to contemplate. Wearing them is like voluntarily locking yourself into an Iron Maiden. Not doing it.

  • Sophia Simons

    I think headbands are just the starting point. I’m for putting anything on your head: belts as headbands work very well. Scarfs as headbands. Flowers or anything really that you can find in the garden.

  • My head is too big for headbands. I can’t pull them off for anything.

  • Leslie Hitchcock

    Charlotte, Your suit. Where is it from?

  • Sara Ashtaryeh

    Leandra–Are you not freezing in that outfit?! Please tell me you are not wearing that on the east coast while I am in thermal socks.

  • johanna

    The headband is awesome for us with too much hair! It removes that big hair away from your face! Thank god it’s back!

  • MargaretInArabia

    No, no, and no. The reason headbands keep coming back is because they keep going away. For good reason.

  • Anna Malcolm

    Wearing headbands is tricky because you run the risk of looking too cutesy or a like a little girl. I like them styled with something a bit odd or unconventional. I also think that the headband needs to be simple if you’re wearing an outfit that doesn’t need an accessory front and center. I actually think that Leandra wore the headband best because her dress is unusual in structure but simple because it’s one color, and her heeled shoes keep her from looking like a little girl. Love the ‘Stones shirt with the plaid outfit, but don’t like the pink headband with it. Would love to see a gold one with that outfit or one of those J.Crew tortoise shell ones. Not a fan of the headband with the jeans and blazer, it just looks unnecessary or something? (sorry!!) Always enjoy the style galleries though-keep them coming please!

  • therealdp

    amilli, you know VERY WELL that no grown woman has any business in a headband

  • LilyP

    headbands hurt. and i think the headband and earrings killed Lupita’s beautiful look. superfluous.

  • Lauren

    Your Becky the Marginal Friend analogy is a bit too Mean Girls for me. I’m out.

  • Ellie

    I wear headbands all the time as accessories, but i have short hair and bangs now. I absolutely hated them when i had long hair.

  • john
  • Tuva

    As I’m growing out my bangs and I’m wearing headbands all the time. Actually I just purchased seven new ones after not wearing it since childhood. Though that may actually point to the fact that my bangs is quite a failure and headband is the absolute ultimate savior. So, yes to headbands!