Fashion Question: Can you still wear a headband after 40?

Hi JoJami and Deborah –

Headband Young

I have seen all kinds of head-wear lately – cute little headbands with pretty accents (see picture on the right).  I’m wondering if those types of head-wear are appropriate for over 40?



Thanks, Tamara for sending in this question!







We posted this question over on our Facebook page and we got so many comments that we wanted to share them with you all here as well!

While a simple headband can be fine no matter what your age, when you start trying to add all sorts of flowers, bows and large do-dads, then you are treading in some risky waters!

The young gal in the photo certainly looks adorable in this headband and it works well with her romantic lace top, we feel the effect would certainly be different when you add maturity into the mix.

With fashion tips, it is a good rule  never like to say “never,” however, we would highly recommend that you think twice about trying this hot trend. While we’re sure there is someone out there that could pull this off, for the rest of us… trying to sport a  large, flouncy bow, well… it might come across as almost “costumey.”

We suggest leaving fancy headbands to the younger set.

What are your thoughts on headbands?  Please comment below:


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  1. Heather says:

    Well I’m not quite 40, almost though! But I wear headbands in my short hair(pixi cut). I think they look cute and sometimes I like pops of color to brighten the day! I think that’s a perk to getting older…I don’t have to be told what I should or shouldn’t wear! Hahaha!! I say wear what makes you happy life is too short to worry about what other people are thinking of you big bow of a headband!!

    • Sherry Lee says:

      Heather, I agree 100%! Why not? And who cares what others think? I don’t. I’m 54 and I do my own thing. I’m not going to wear a big bow or a big anything on my head, for that matter, with the exception of a straw cowboy-style hat at the beach to protect me from the sun. But that is my taste and my preference.
      And really, what’s with all these rules? Based on age? Consider if it looks good on you, if you like it, and do what you like. You only live once.
      I’m wearing a headband now as a matter of fact. I have shoulder length dark blond hair, my natural color, and it looks good on me. This one happens to blend in with my hair color, but if it contrasted with my hair color, I’d still wear it If I liked it.
      Are we in grade school, worried someone might not like it? Nope, we are not.

  2. Anyone can rock a great headband. Always have to remember that certain headbands are appropriate for certain occasions. Thanks!

  3. I get a little tired of everything being put into an age bucket…If you love headbands and you can pull the look off..then wear them…In fact the older I am getting the more I gravitate to the big flowers and bows and all things pretty…I think women especially think that when we reach certain ages we have to change how we look…I think that there is nothing more aging than dressing down and wearing drab colors.

  4. If Hillary Clinton can wear on and the mother-in-law on “The Good Wife” can, I guess if it’s one in good taste, why not?

  5. Sure! But I agree with the less is more comment above. :)

  6. if you like headbands, and they look good on you, wear them! I don’t see an age limit for this useful item. They really do help the hair stay out of your face & provide a cute & quick fix for some folks on bad hair days!

  7. My comment re headbands is absolutley not – EVER. Dont go there! It is far too twee for anyone over 35. There are other wonderful accessories out there without having to resort to headbands or girly bows and ornaments. It just makes you look sad and stuck in a time warap.

    • Hi Janice,
      I’m wary of ever saying “never”… really some women can pull of a simple headband, but your are correct when it comes to the fancy ornaments a little too tween for sure!

  8. No.

  9. To me, on someone over 40 many headbands would look overstated, and sometimes frivolous and undignified. I can see something narrow, and tortoiseshell or a color close to the hair color. Or, a wide scarf-type with an outfit with a casual, artistic look, but aim for some level of sophistication and simplicity. The headband-with-bow in the photo is so pretty. I think it would look good worn with a well-made white or ecru button-up blouse, in a dressy cotton, with simple gold or silver ball earrings and a strand of pearls. I think if I were to add detail with the hair band, I would keep the rest of the outfit around the face clean and simple.

    This question reminds me of when, in 1991 and 1992, Hilary Clinton wore headbands when campaigning with Bill. Style experts in the media sort of mocked her for that.

  10. You two are so diplomatic, Why not sport it with pigtails and skip off feeling like Baby Jane?! :)

  11. My vote goes to YES headbands are okay- but NO to any bows or glop! I LOVE to wear a headband in the summer, or just when I have a day of hard work around the house, projects or the daycare days. Sometimes you just don’t want that hair in your face.

  12. I think the answer is, “yes,” if the headband is close to our hair color and we remove an accessory from some other part of our outfit to compensate. For a formal occasion such as a wedding, wearing what the British call a “Fascinator,” (which are getting trendy here in the U.S.,) could work on a similar principle; wear a color that matches or is close to our hair color, or is a neutral. Fascinators are hair ornaments that can be clipped or pinned on to the hair by themselves, or they are often attached to headbands. Restraint is key! –Lisa in Massachusetts

  13. Wearing a headband would be a no from me as well. But, since we are in the headgear area I’ve been wondering what would one add to a wide brim summer hat. I’ve seen big floppy flowers but that seems to fall into the headband category. Nice if you’re young or a bride but if you’re older it seems a bit off. What would some alternative be? Especially interesting alternatives. Chic not cute alternatives? Thanks. Pat

  14. I have short, black hair and often use a black headband with a small embellishment. (I have a multi colored jewel cluster, and another with a single, small peacock type feather) Since my hair is short, there aren’t as many style options- updo, pony mane etc so a headband works for me. I keep the rest of my outfit, including jewelry bling-free and use the headband as a fun accessory.

  15. Susan Hartman says:

    If you have always worn headbands you do not have to stop because you are over 40. You may have to tweek the style. However, if you have never worn them there is probably a reason. The reason probably still exists. Some people ae not headband people. I am not one as mush as I would like to be.

  16. Aliceann Toole says:

    Hi — I’m kind of on the fence here … headbands here in the South are very Junior League and I see a lot of ladies wearing them. I wouldn’t wear them myself because I think they look dated, but I do like narrow decorated headbands with interest on the side for dress-up/evening … kind of an homage to those fabulous vintage cocktail hats. And that leads to a follow up … what about fascinators?

    I recently was visiting my sister in England and went to a consignment shop with one of her friends. I picked up a fascinator and asked how it should be worn. The friend sort of pinned it in the side of my hair; when I looked in the mirror, I realized I ROCKED the fascinator. I started hoping I could marry off one of daughters or attend a charity ball just so I could wear one.

    It seems to me that if a style looks good on an individual, or if, like me, they’re pining to wear a fascinator, why not? At worst, other people may nudge each other and mumble a comment behind your back; at best, you may have fun and feel fabulous.

  17. I have a Burberry headband I love to wear– and it is a neat styled look in my long hair and makes a complimentary accent to the Burberry lining touches in my jacket and cuffs…looks great with Ralph Lauren Polo shirts too.
    I also wear Lilly Pulitzer headbands Lily shifts and with Lilly Polo shirts as it all compliments a total look. Though I am from Florida so we naturally love our Lilly-it is a look I see sported more and more in Beverly Hills, West LA and Newport Beach.
    I have a cast off Abercrombie & Fitch of my 12 year old daughter I wear with an A&F pink and blue flannel she has outgrown–its one of my favorite casual run around looks with jeans and cowboy boots.
    I get lots of compliments on them—and in fact find I would wear them more if I didnt have to wear hats and sunglasses to protect my eyes and skin…

  18. Too “little girl” after 40!!!

  19. Subtle colors and “less is more” would seem to be two good ideas to use when planning on hair accessories, otherwise you might look like you’re trying to be 16 again. But that’s just my opinion. Good topic tho as I’ve noticed alot of younger girls wearing them!

  20. I wear headbands each day. They are not poufy or have large bows, but they are decorative. They are typically quite classic and elegant. I have pearls and onyx and leather. I do have a few that have crystals on them but they are understated. I have to keep my hair out of my face and it looks better than throwing it up in a ponytail and I have trouble putting my hair up. I think the half ponytail look appears too youthful. I guess it is a matter of taste.

  21. A big NO from me I’m afraid, a little bit too try hard.

  22. Jamie Hall says:

    For me, the answer is no, though I’m sure that there is someone out there who can get away with it. (Though I would dare to say, that it would have to be “understated” for them, as well:) Just my opinion. Great topic! Jamie in AZ

  23. Absolutely!

  24. I have been asking friends this question because I love headbands with huge bows and I am over forty. I have found that if I stick to a color close to my hair color, it doesn’t look so costumey and has a better look.
    Thanks for your blog! I really need it! I tend to get carried away and dress like my teenage daughter!

    • HI Sandee,
      That is a good point about picking a headband close to the color of your hair…that way it will blend in more. When you have a teenage daughter in the house, it makes you think twice about what you are going to put on. Thanks for sharing, your blog is really nice too!