What’s The Most Drastic Hair Change You’ve Ever Made?

I’ve had a short bleached white pixie cut for over two years now. And I’ve been thinking it’s time for a change. I’ve been thinking about a dark brown chin-length bob with loose curls and bangs (maybe like this?). I’m not sure what’s motivating my urge for a new hairstyle (maybe the move to France?), but I keep thinking about it.

Here are some of the factors I’m mulling over as I consider a hair change:

-Daily maintenance
This is a big one. I don’t love a long or involved daily grooming routine. Right now, my hair takes so little time on a daily basis. It’s amazing. I don’t have to think about it. I don’t need a hairdryer, flattener, or curling iron. I don’t need a hair tie around my wrist (though I still carry them in my bag because I have four long-haired kids). And my hair is so short that hiar products (purple shampoo and shine wax) last for a loooong time, like a year.

When I wear my hair longer, it takes more daily maintenance, period. To manage it, the last time I had long hair, I would schedule a weekly blowout and then make it last for 7 days — using dry shampoo and top knots as the week progressed.

Ideally, if I go for the bob I’m imagining, I’m hoping it won’t be as much daily maintenance as when I’ve worn my hair long .

-Cut maintenance
With my pixie cut, I have a hair appointment every 4 weeks. No negotiating. With a longer hair hairstyle — even chin length — I can go much longer between cuts.

-Color maintenance
Managing color is probably what I’m thinking about the most as I consider a new hairstyle.

As I’ve discussed before, I grew up with dark brown hair, but I started going seriously grey in my twenties, and these days my natural hair color is a mix of charcoal and silver grey. I don’t really mind the color and I’ve happily worn it in it’s natural state. But when I do, it always reminds me that in our society, grey hair equals retirement-age grandmother or older. (When I wore my hair grey, I remember Flora June’s classmates asking me if I was her Grandma on a school field trip.)

I was thinking about why this is, and my theory is that a whole lot of women, even those who go grey in their late 40’s or early 50’s, cover their grey for as long as possible — for decades sometimes. And because of that, I don’t think we’re used to seeing middle-age grey-haired women, and we only associate grey hair with the 70+ age range. Just my theory.

I don’t mind being the age I am, but I do want to look my age. And I think my grey hair makes me look older than my age.

Right now, I get my hair bleached white every other month. As it grows in, the roots look dark and it adds depth that I really like. In fact, I like my current hair color best after the roots have grown in for at least 3 weeks.

When I have any-color-but-white hair, I don’t like how my roots look at all. Instead of coming in dark, they look white/grey against the dark hair and drive me nuts. I end up wanting to color my roots every couple of weeks, and since I don’t have time for that many appointments, I end up doing touchups at home, which is a pain because I’m not very good at it.

-Growing out a pixie
Have you ever grown your hair out from pixie length? It is not fun. There is like a two year awkward period. I wish I was exaggerating but I’m not. I’m thinking I’ll need to choose a wig to help me out through the worst of it.

-Settling down with one style
I really like my hair in a pixie cut. I feel stylish and modern. And I like the idea of finding your ideal hairstyle and then sticking with it — like Anna Wintour. If I have an ideal hairstyle, it’s probably a pixie cut. So I ask myself: am I crazy to change it?

But then, if I assume I’m going to live a long life, then I feel like I’m already bored thinking I won’t change my hair again for 40 years or so. So why not grow it out again? I can always return to a pixie cut if I miss it.

Anyway. That’s what’s on my mind hair-wise these days. How about you? Have you ever made a big hair change? Have you found your ideal hairstyle that you’re happy to commit to for the foreseeable future? Do you wear your hair in your natural color, or do you like to dye it/bleach it/highlight it? Has your hair gone grey? If yes do you color it or wear it natural?

54 thoughts on “What’s The Most Drastic Hair Change You’ve Ever Made?”

  1. I have always admired your hair: you have always chosen such lovely, elegant, flattering cuts/colors/shapes. Truly.
    The most drastic cut I made was back in about 2010, I went from hair that went to my mid-back, to being just above my shoulders (I donated it, and that’s where the 10 inches left me). It was so freeing, cliche as that sounds. about 5 years ago I expressed interest in going SHORT-short to my stylist and she suggested we do this gradually, because, as you pointed out: it’s hard to grow out a pixie. So, I’ve had my bob cut becoming more and more sleek and I grew out my blunt cut bangs into a more sideswept option. I LOVE my hair in this shape, and it gets a lot of compliments. After all these years, I finally found hair that makes me feel like Myself. I like that it takes very little effort to make it look polished, and when I want to get fancy, I just wear a cute headband.
    My hair has in the last few years begun to show some white strands, and I asked my stylist to add in some highlights (my first time ever adding color to my hair), to make it look a little more multi-hued, so as to gently ease in the white strands. I don’t hate them, because we all get older (And I love this older, smarter, more fun version of myself more and more!) but I want to enjoy my brown as long as I can before the white takes it. ;)

  2. This is a great post. One of my best friend’s is a hair stylist and he has cut my hair for the last 25 years or so. And often. I have had everything from the bleached blonde pixie cut to long and dark. Now that we don’t live near each other, my hair has gotten long with growing-out highlights (and a bit blah at the moment tbh). I totally agree that life is long and hair is there to be played with. I’ve had hair cuts I have loved and some that have taken a lot of getting used to (one time I came home after a pretty drastic cut from very long to pretty short and my then 4-year-old daughter could barely look at me she was so upset “It’s like I have two daddies” she cried. Tough crowd.) Change it — like you say, you can always go back. (The pixie cut does suit you Gabby.)

  3. I’m 62 years old. My original red hair is now auburn and I am just beginning to get greys. I’m not dying my hair because I have no patience for sitting through the process and because I can’t imagine it is good for my hair or health to put so many chemicals on my head. I am also someone who rarely gets my hair cut – maybe 3 times a year – and can’t imagine going more often. When I was younger I routinely changed the length of my hair every few years. I love short hair on women. But, I shy away from short hair now because I have gained much weight and have a full face. Upon my retirement a few months ago, I took the opportunity to have bangs – full-on bangs – something I would not have done when I was working because they didn’t look appropriately professional. I loved them at first, but could not keep up with the appts. to maintain them (and was not good at cutting them myself) so am now letting them grow in. I am aware I may change my mind about dying my hair once the greys really come in…and I will not fight it if I do but, I will be surprised.

  4. I feel like I’ve had varieties of the same hair cut forever-maybe because my hair is very fine and on the thin side-can’t do too many different things with it. I do get it colored every 4 weeks. It’s gone from way over highlighted (which looks so silly when I see a picture of myself with it) to a more natural brown. I’m 53 and I have so much grey-hence the coloring. My youngest child is 11, and I definitely do not want to look like his grandmother!

  5. I like your idea for a curly bob! I too love short hair (really short) and love it on myself but my mom would always say that my features were too sharp and I needed more softness around my face. I hate her constant critique of my face and hair, and since I loved short hair, I’ve kept it for several years (before that I was wearing my hair shoulder length with bangs and was able to make its curly self easily straight just my blow drying it. But my mom hated that style too! But I loved it and kept it for about six years… Now I’m thinking that despite my mom’s annoying critiques, she is right, and esp as I age and my features sharpen, I could use more softness around my face. I had a great last cut, so now it’s growing out pretty well, and the curls are back. At 72, my hair, though it has a good number of grey hairs, “reads” as quite dark brown. This on the one hand makes me look younger, but as a face ages, and wrinkles and droops a bit, I think light hair, whether grey or blonde gives a softness to the face that dark hair doesn’t. SO MANY considerations! And, yeah, the hair does frame the face, and can definitely affect the way we see (and feel) about ourselves. I wish it wasn’t so, but so, it is.

  6. Funny how hair has been on your mind lately because it’s been on mine too! I moved from my tried and true hairstylist (not far, but far enough to make it difficult) 7 years ago and I STILL haven’t found someone I absolutely adore by me. I just messaged my former hairstylist and made an appointment because I want to LOVE my hair and I need someone I trust. I’m debating a reverse ombre/baylage look with the dark on the bottom – but I’m just not sure how it will work. Your pixie cut is my favorite – but your naturally curly hair is too cute.

  7. It’s funny, I’ve been following you for a long time and we’ve met a few times at ALT, but in my mind you always have a curly longish brown bob, like the photo with the beret or the top one. Maybe because you had that cut the years we met in person? I love that cut on you ;)
    I’ve had different cuts over my 45 years of life. Pixie as a child, long with bangs, blond highlights, straight bob, never as extreme as your changes, but I need change to keep things interesting.

  8. How timely! I am in the midst of a big hair change now. In fact, I’m almost one year into growing out a pixie cut so by your timeline I have another year of awkward. (I’ve joked – seriously – that it’s a years-long awkward stage, and you’re validating that!) And it is awkward. I go through lots of days where I do not love it. It helps that sometimes other people think it looks good when I don’t (that’s happening lately), which keeps me hanging on rather than cutting it off.

    I’d had the pixie for about 10 years and it kept being on my mind to grow it out – maybe shoulder length. I started to get inspired by following @grombre on Instagram. So many of those women have lovely, longer grey hair.

    Like you, I started greying in my 20s. I’ve just let it do its thing and the front is very silver now, shot through with some brown. There is still a renegade brown patch at the nape of my neck. I’ll be happier when the greyer top grows long enough to cover that. I actually really like the grey and I have no plans to color it.

    I’m hoping I like the longer style. I also like not having to fuss with my hair. I’m not good it and I don’t have the patience to learn. I also hate taking the time to do it. So I’m looking for something that is easy and that I will like.

    For now, I’m just committed to staying the course so I can see what it looks like long. I wouldn’t be surprised at all if I decide to go back to a pixie at some point. I do feel like that’s my spirit haircut!

    I think if it’s on your mind, you should try it. Nothing ventured, nothing gained and all that. :)

  9. I have a white streak on one side that I let grow; there’s no covering it anyway, but I dye the rest near my natural brown because I don’t like the messy “sprinkle” of gray hairs. I really like it this way. I feel like the brown keeps me young, but the surprising white shows my age (45).
    I’ve grown out a pixie a few times. I thought it was fun, mostly. A new look to work with every few months.

    1. I’m 44 and have exactly the same hair, except my white streak is right in the middle of my forehead! I get a lot of positive comments on the streak, but people do tend to think I’m younger than my age.
      However: I’m finally ready to let the rest of the grey come in. I started greying at 30 and covered it first with highlights, then with full-on colour… but I’m tired of all the chemicals and the time lost at hair appointments! I’m not looking forward to the ugly months of having a line between the dye and the greying roots but I think it will be worth it when my hair is fully back to its natural state.

  10. I love your blond pixie! That being said, when I was young, like early elementary school, my mom made me have a pixie cut much against my will. I now am 48 and have been wearing my hair long since I was able to make my own decisions about my hair. I’m not sure if my hair is long because I’m still making up for the enforced short hair or if it’s because I have always loved long hair. Maybe a bit of both – rebellion and preference mixed : ). I have strawberry blond hair that has faded and grayed in places though everyone insists that you can’t see gray. I’m sticking with my natural hair color but I may not have if I was really gray. Have fun with yours! I love the Fleabag short cut too!

  11. Speaking of Fleabag, the scene where the sister gets a short cut that she hates (“I look like a pencil”) and Fleabag calls it “French” to console her comes to mind when you mention being influenced by French style : )

  12. SAME! I am 45. Two years ago, I cut my hair super short and grew out my gray just to do an inventory check (how gray am I?!!) I decided to keep it natural and have had various “edgy” cuts that I was hoping would make me look youthful even with the gray. I think it is working… I get a ton of compliments, but I sometimes I feel like I am just being complemented for being “brave” to have gray hair!

    Every once in a while I see a picture of myself, and I’m like geez I look old, especially if I am not dressed up or styled. I, too, am considering a return to hair color. We can always go back, right?!!

    Also, growing out a pixie is rough, but I’ve had alot of fun in-between styles that I would never have considered (even a mullet!) I know you will rock what ever look you choose! I can’t wait to see what you do :)

  13. I would be interested in learning about the process of dying hair white. I love the way it looks and with my grey, silver, dark brown hair, i have felt maybe white is the way to go.

    I would also like to hear about hair loss for women and different types of treatment. I read about using rograine, but worry that is too harsh. Any other ways to treat this?

    PS I love your white pixie look, but have also enjoyed watching you have fun with changing your hair over the years.

  14. It’s nice that you have a face shape that can work well with so many cuts (and the option of curly vs. straight too)! I would like to be more experimental with styles, but have a very square jaw line and small features so short cuts are too severe (I have fine, mostly straight hair, which also cancels a few options). I started graying in my 20s and have gone through all the shades of brown, red, blond and (almost) black hair. About 3.5 years ago, I stopped dyeing my hair (for the chemical consideration and also because of the root maintenance). I go back and forth about how I feel about my whites/grays. The color is very uneven and I wish it would just all grow in as white/gray. I do feel old some days; other days I feel like it doesn’t age me and that it looks way better than the dye ever did. I moved to France a few years ago and love the French style and seeing everyone do their thing with such confidence. Lately, I see more people my age rocking their natural hair. I love not dyeing my hair as far as maintenance goes, so I think I’ll stick with my natural look (and I’m having fun with my lipstick instead…). Can’t wait to see what you decide to do!

  15. I love your white pixie—it looks so edgy and cool. Why not just get a few good wigs? I lost half my hair last summer (pcos? Androgenic alopecia? Pre menopause? Who knows!), and discovering the world of toppers and wigs has been an unexpected joy! Now I don’t have to commit to any look—I can have all the looks—black, blond, curly, straight, short, or long. I was so worried about trying them, and now I wonder why we all work so hard to have pretty biological hair! Haha

  16. Could never bring myself to color as you have to do that until Jesus comes back, don’t you? ;) Looking at the photos you’ve included here, I think a darker hair color warms your complexion and looks more natural, fwiw. I let my curly hair do its thing (and I have ALWAYS kept bangs going, even though some say it’s against curly girl code). My aunt went grey when she was 19, and we never gave it a thought – it was just a part of who she was, and she was beautiful. I don’t remember her ever commenting on misperceptions about her age – but she was always very active, as it sounds like you are, also. I say go for the bob – but I have very, very low hair-annoya – it will grow, and I can cut it off again .. whatever. Hope you find a style that you enjoy and that makes you feel your best!

  17. I have long brown hair, a few inches below the shoulder. I’m 58 and have been having my hair professionally colored for 25 years. I have to get it colored every four weeks and would love to get it done every three weeks, but it’s expensive. So I use my little L’Oreal color spray the week prior to my appointment. At some point, I guess I have to go gray, but I’m just not ready for it (although my pocket book is 😂). I’ve always had long hair and I love it. I have bangs and I curl it each day. My sisters both have short hair, and always have, and they have let theirs go white/gray. One sister is completely white and has a cute, youthful cut and it looks great. She is naturally a blonde. The other sister had really dark brown hair and had it highlighted a few months ago to grayish shades so that she could grow her hair out gradually and not look so frumpy. Her hair is grown out now. It’s white on top and salt /pepper in the back. She’s pleased with it. I’m just not ready for that. I, like you, hate to see the gray/white roots coming in. It really bothers me. So I get it colored. I don’t want a short hair cut. My question is, do I go to a light brown so that as I age my gray isn’t quite as noticeable? Having long hair and having dark hair as my natural color makes it tricky. My blonde haired friends’ gray doesn’t show nearly as much as mine. Oh the joys of hair color and aging!

  18. I wear a pixie, which works with my baby-fine, straight, still-natural blonde hair. While I have serious bob envy when I see a razor sharp, jawline cut on someone, my wispy stuff just won’t do that. Whenever I see another woman with a pixie (which signals lots of self confidence, IMO), I think: another member of the club!

    Gabby, I love the pixie on you. Even after you make the change you’re considering, I’ll think of you as a Pixie Club beauty.

  19. First: everything looks great on you! Pixie looks super elegant, you have the perfect neck for it. But I totally understand your wish for a change.

    I‘m dark brown curly by nature. Dyed my hair blond in my twenties, straitened them. Had them long as a mother of young children because it was convenient. Then went for short hair and I just grew out of it after 1.5 years of patience. Meanwhile I’m 48 and I dye them since a good year because my children prefer it 😊.

    Your idea about the curly bob is nice. Why don’t you try!

    By the way, my idol is Linda Rodin… she’s so elegant with her grey hair! I love the idea to become a silver fox one day …

  20. I had shoulder-ish length hair until age 15 when my friend and I both cut our hair off, into pixies, in my backyard. I’ve buzzed it, had mohawks, asymmetrical cuts, bangs, and on two occasions in the last 20 years, grown it out to my shoulders again. It took forever, and while I liked seeing my long hair, I didn’t feel like “me.” I think having short hair for so long it’s become part of my identity and long hair is the daring move. And I’m okay with that.

    Your pixie might be my favorite, but I’m sure you’ll have fun with whatever you choose to do next.

  21. Growing out pixie cut brings back memories! It was a great style (except for frequent haircuts, and on occasion, nothing to hide behind. My reason for growing it out was that longer hair looked better on younger women, and I could keep it as an option for when I was really old…like 40 or so! Nearly 50, still haven’t gone back, and trying to go gray gracefully. It was worth the pain of growing out, and still good to know I’ve got a good go to style if I don’t want longer hair any more. Look forward to seeing what you do!

  22. I have longish hair that I’ve had colored every 5 weeks for 40 years. I hate the expense and the health implications, but I hate my roots more. I agree that I don’t mind looking my age, my I feel my grey hair ages me.

    Growing out my bangs this year was tough – I can’t imagine growing out a pixie cut, although I’ve done it myself and found headbands to be the best solution to the problem.

    You make such fun choices with your hair and you clothing – I look forward to seeing how you move forward!

  23. I have lived with my natural grey (from my original black – like you I started getting grey hairs in my twenties) for the pure reason of sustainability & env impact. It is difficult to go against beauty norms as we’re so conditioned to see women with grey hair as being 60+. Thks

  24. I cut my hair right before giving birth and it was WAY TOO SHORT for me. She went Pixie (which I did not want), coupled with post natal hormones, I was a wreck. I never colored my hair until about 5 years ago when I went red and I LOVE IT. The maintenance sucks. But, my hair had never been a big thing until I colored it and now it’s gorgeous and gets all the compliments. I don’t have much gray so the root issue is negotiable (right now).

  25. I wore my hair ultra-long until I was about 27. I found my soulmate hairdresser who chopped it down to just below my shoulders, which I wanted to love but felt like I was betraying my pro-long hair self. After the invention of the tangle-teezer, cutting my hair to mid-length was the most liberating achievement in hair maintenance.

    My current go-to-do is eyebrow-length fringe/bangs (one girl who trimmed them basically called them ‘Russian S&M bangs’ and I find that hilariously accurate), and shoulder-ish length hair. I would LOVE to do a pink ombre, and grow it longer over the winter, but A. I am terrified of bleach and B. low maintenance is my jam at the moment. Getting my fringe trimmed every 4 weeks is already more upkeep than I wanted; I have a lot of respect for anyone who maintains colour, perms, or chemical straightening long term because I couldn’t.

  26. Seriously, this is what I’m talking about! I commented recently on your more serious post about gun control because I just finally had to let you know how much I appreciate how you frame these types of discussions. Then you write a much more trivial piece about hair, and I feel the exact same way! Like, you are so upfront about being comfortable being your age, but stating your opinion that certain styles make you look older and you want to look your age. I don’t even know how you do it, but I’ve been following you for over a decade, and I come for your lovely, lovely voice. Thank you for sharing it.

  27. Also, I enjoy all your looks and how easily you approach hair changes. It’s always a drama for me to do something different and I always hate it so I come back to long, curly, layers with occasionally high/low lights. That way I can cut my hair once or twice a year. Can’t wait to see what you do next!

  28. RebeccaNYC (mybackstageopera)

    oh lord have mercy, I have done EVERYTHING to my hair, too, except grow it really long. And I echo everything you have said. I have gone from chin length bob dyed blond with subtle highlights to pixie dyed white and back again. I have sort of settled down to letting my hair be it’s natural gray with variations of short cuts. Right now I am letting one side be longer and the other be short, and I am contemplating dying it bright white again. The good thing about dying it white when it’s short (in addition to the roots looking so great as they grow in) is that it does not fry your hair like it does when you dye your hair white when it’s long. Can’t wait to see what you do next! (one of my friends with a white pixie dyes it neon PINK. It looks amazing)

  29. Try the curly bob – its also very French in an Ines de la Fressange way. You can always go back to the Pixie. There are many many years of haircuts ahead of you!
    I’d love to know what to do for thinning hair age 40+ – A post on that would be super!

  30. Um… I feel like I could have written 99% of what you’ve said here verbatim — from the current pixie cut, to the debating about growing it to a bob, to the going gray in my 20s and the conundrum of societal expectations, to the wondering if I should declare a pixie as my signature cut or still experiment in my 40s, even with the challenges of growing out a pixie.

    The only difference is my hair is currently dyed brown, but I like your points about the dark roots with a bleached color! 😂

    I really don’t know where I land on this either, but I find myself thinking about it an awful lot these days… I SO get what you’re thinking here!

  31. I think by the time women get older, say 60+, they look best with moderately short styles or worn up. That being said, it’s nice for girls to wear their hair longer while they’re still young. You look classy in all of your styles but my favorite of your four pictures is long and curly. It looks like you. : ) The curly bob also sounds great.

  32. Have you noticed the movement in this country of women to go grey? Have you seen Keanu Reeve’s girlfriend, Alexandra Grant, who has grey hair, and it is beautiful. I am a member of a Facebook page called Silver Sisters, which is a community of women in various stages of going grey. I am currently in the process of letting my hair go grey after coloring it for 18 years. I have stopped using permanent color and now use non permanent color until the permanent Colored ends grow out. I may eventually get highlights and use a silver toner until the greys grow, and I can go completely natural. My hairdresser is helping me with this process. I expect it to take 6 months to a year, and for some women it can take up to 2 years. I am looking forward to it, and I think silver hair is beautiful! I think that women are tired of the double standard of it being just fine for men to go grey, while they feel society’s pressure to dye their hair, and they can’t be natural. I will also be glad to stop using harsh hair dye chemicals which some studies have linked to cancer. I think your hair looks great in the pixie cut, but would also look great in a bob style. I encourage you to try letting it be your natural grey color!

  33. My first gray hair came at 19 and I was coloring by 26. For my 47th birthday, at my then 17 year old daughter’s urging, I gave myself the gift of being bottle free. I had my new my silver hair cut pixie style and I have never, ever looked back. The amount of compliments I received really caught me off guard, in that so many people said how great I looked. That was 7 years ago and in hindsight I think what those people who commented on my hair saw was the confidence of a woman who bucked the “gray means old” mentality and dared to be who the heck she is. I am proud I sent that message to my daughter. I use power tools for a living, pilot airplanes for fun and have silver hair, in other words, “I am woman, hear me roar!” :)

  34. I’ve gone from curly (natural for me) to straight, long, short and have somewhat settled on in-between. I straighten my hair every 5-6 months or so to minimize the time it takes to dry. Growing it out is a pain. I suggest a cute hat and fun barrettes for the awkward days.

  35. My hair and I are in a constant tug-of-war :) Generally speaking I grow it out for a year and a half or so, chop about 10 inches off to donate, and start all over again. I like how it looks when it’s shoulder length and layered, because my natural waves fall really nicely, but I also like being able to pull it up in a bun or braid it, both of which are difficult when it’s short. So again, a tug-of-war.

    I also had a hairstylist in Memphis for years whom I loved; even when I lived in India, I would wait until I came to visit my parents to get it cut [which sometimes meant I went up to 8-12 months without a trim!] because she did such a good job and knew exactly how my hair would fall. Well, she moved about 2 years ago, and I’ve not found my person again yet. I have one who I like pretty well, so I’m hoping another visit or two to her will help me figure out what to do with the mess on my head. I am also all about low-maintenance hair: I wash it every 3 days, and that’s it. I don’t dry it, I don’t comb it, I don’t put any product in it. Every few weeks or so I’ll put coconut oil in it for about an hour before washing it out with shampoo and hot water, but that’s it.

    I, too, love the drastic change of chopping off 10-12 inches and seeing how different it looks and feels. At the rate I’m currently going I’ll probably be doing a big cut around August, so stay tuned!

  36. I love how brave you are with your hair changes!

    I follow the Grombre instagram account for inspiration and reassurance that gray hair looks great on younger than 70-year-olds.

  37. I am 45 and have never colored my hair! When I was younger, I was never really tempted – I liked my hair color. Now, for the first time, I’m considering it. I have been getting grays for a few years, but I don’t mind them so much. What I mind is that over the years of spending not enough time outdoors in the summer, my hair has gone from have really pretty natural highlights to a flatter mousy color, and I don’t love it. However, the idea of hopping on the hair coloring treadmill makes me queasy. But also, maybe I should just try it? Torn.

  38. I love you with brown hair and perhaps a bit longer. I was a platinum blonde, over the years became dishwater blonde, and now I get highlights. I can’t go natural cause it is beyond drab. I am very fair and will continue with the lighter highlights until I can’t take the cost any more. Then I’ll figure out the next step.

    Looking at all your photos, I really think the brown becomes you – and de-ages you!

  39. I love this post, love reading everyone’s stories and think about this kind of thing now and again.

    I am 39 and have steadily grown more and more silver over the last 10 or 12 years. In my 20s, I wore my hair it’s natural almost black, but dyed it every color under the sun including blond, red, purple, red, and ombre. It was fun, but took SO MUCH TIME and lots of money. A lot of what I was doing was for the joy of it, but it was also in the hopes of being seen by people. Now I love being seen for who I am with my gray/white, black and shiny curly hair.

    I love it for many reasons. I love the statement it makes, I love what it teaches my children, I love the savings of time and money and worry, and I do get so many compliments on it. That being said, a couple of times in the last five years people have glanced at me and thought I was a grandmother and that is confusing and stings. But much more than that I am told by friends and colleagues that they love my hair, that it inspired them to go natural, and that my hair glows.

    Gabby, it is so interesting to me that there are so many ways in which you are a leader among us but that in this one area you sound fearful of aging. Why not try a gray and curly bob and see what it feels like for some time? This is the perfect time to try gray since your hair is so short already?

    I will say that I also understand the joy of experimentation and never look at people differently for playing with their looks. I just hope it is not from a place of fear or expectation.

  40. Wow! You have had so many amazing and beautiful hairstyles, and it makes me reflect that we are absolute hair opposites. With the exception of a short stint in college where my hair was in a pixie (it was the late 90’s, it is not my ideal cut), and the subsequent growing out, my hair has pretty much stayed the same – long, layered, blow-dried straight with no bangs and a side part. It is my defining “look”. I have always LOVED my natural color and have never dyed it for fear of “ruining” it in some way. As I’ve started a little Stacey London streak of gray (naturally), I’m curious about whether I should embrace it (it lends some gravitas at work, where I am a fundraiser), or hide it in highlights.

    I love all the photos. I’m sure whatever you do next will be gorgeous, and I will live vicariously through your playfulness!

  41. You have tried so many different styles! So fun! I too love the idea of a hair “uniform,” it’s such a time saver, and having a default style makes me feel like a grown up. It’s true that a short cut means more trims. I trim my own hair with a Feather razor- easier than scissors and so much cheaper than the salon! I taught myself from youtube. I do miss the experience of getting a hair cut, though. I have some greys/whites that really sparkle in my dark brown hair, and right now I don’t plan to color it. This is what 35 looks like, people!

  42. My hair first started going gray when I was in my 20s, and I had a pretty well-established white streak on the side by my 30s. I’m in my 40s now and, while the gray has spread a lot, I still have a pretty prominent streak. I never considered dyeing my hair, maybe partly because my mom never did (she had gorgeous gray streaks at her temples — people always thought she had it done). I am constantly amazed at how many people compliment my hair, including complete strangers on the street! I think you’d be surprised to find out how many people really like the way gray looks.

  43. Growing up, I had long somewhat wavy hair. When I was really young, it was blonde, and it got progressively darker as time went on (it’s a medium brown now). I never cut my hair until I was in high school, and even then I cut it to shoulder-length and once a bit shorter than that. My freshman year of college, I went the shortest (to this date)- which was a chin length bob. I also did an angled bob (about chin length in front) when I was in the Peace Corps. I liked that haircut a lot! But I didn’t have a shower for awhile and basically wore it up constantly because it was too much effort without running water. I’ve worn in longer than shoulder-length since. I like my hair this way, but have been itching for a change lately. I know it’s just hair, but my hair takes a long while to grow out. I’ve never dyed my hair, and don’t plan to until I go gray (I have some gray hairs, but not enough for it to be noticeable).

  44. I am 48 and just started going grey in the last 5 years. I have a 6 year old and a 9 year old and was just asked last week (by an older woman!) if I was their grandma! I have a young looking face so I was surprised by the comment. I feel much younger than I am and this really threw me. Im not planning on dyeing my hair for financial and health reasons. I too have a pixie (which is my signature haircut. I love it but also it works with my thinning hair.) Just have to say that you look great with all your hair looks but I think you look absolutely gorgeous in the pixie photo with the long blue earrings. You look modern AND youthful.

  45. Looking into getting rid of gray hair for my husband, who has gotten more gray in the last few years, I came across something recommended by goop but haven’t tried yet. A product called hairprint.
    https://goop.com/beauty/hair/ask-jean-non-toxic-hair-color/ It looks like something that draws out your natural hair color through a chemical reaction…and apparently is also safer than dye. We have yet to try it but it sounds great and if effective, relatively cheap at <$50.

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