Things You Shouldn’t Wear After 50

Google ‘what not to wear after age 50’ and you will have your pick of thousands of articles telling you what looks terrible on your old ass body.

I want to point out to the writer who wrote the ‘no-no’ article, you need to remember you are writing for women over age 50, not preschoolers. I don’t think I’ve said ‘no-no’ since my youngest was a toddler.

We could spend hours studying the clothes we shouldn’t wear and the slang we shouldn’t use and the makeup techniques we need to retire.

Here’s me, weighing in on this topic.

You are over 50 for fuck’s sake. Wear whatever you want. If you’ve made it to 50 and still need to consult articles on how to dress appropriately then you are so missing out on one of the best things about being over 50. One of the best things about getting older is realizing that we don’t have to spend our energy worrying what other people think and we get to be comfortable in our own skin with our own freak flags.

Still, there are a few things that women over 50 really shouldn’t wear:

The weight of the world. When you wear the weight of the world on your shoulders, you age. If you like the feel of the world’s weight and don’t want to give it up, then try scaling back a bit. Perhaps just wear the weight of a few of the smaller continents. For instance, I am only wearing the weight of Australia and a made up country called ‘Michelloponia’. I think they have a slimming effect.

Shame and regret. So few people can carry this look off. Most of us just end up looking haunted or like we were forced to eat liver and onions. Shame and regret are especially hard to wear after fifty. Wearing shame and regret past fifty is one of those things that make your eyes all red and runny looking. The downward spiral just snowballs from there. Once the eyes get old lady looking, then you have to re-evaluate the wisdom of black eye liner. I say give up wearing shame and regret and fuck giving up on black eye liner.

Rose colored glasses. Oh, sweetheart, you know who you are. Those glasses do nothing for you. Not only do they make you look like you’ve been smoking weed for days, they also keep you from examining life and your surroundings realistically. Yes, reality sucks, but by the time we hit fifty, we need to suck it up, take those glasses off and dick punch reality into submission. Or just get some really big dark sunglasses instead. They cover all manner of sins.

Stiff upper lip. There is a time and a place for the stiff upper lip, but damn, it can’t be worn all the time. Too much stiff upper lip causes those funky vertical lines between your upper lip and your nose holes. We don’t always have to be stoic. I’m not suggesting that you wear your heart on your sleeve, but that is a  much softer look than wearing a stiff upper lip.

Too many hats. Personally, I can’t pull off wearing one hat much less many hats. I don’t have a hat head. My hair poofs out and my ears look like car doors when I wear a hat. Wearing too many hats just exacerbates these issues. When you wear too many hats, it’s easy to forget which hat you’re wearing. For instance, are you wearing the ‘no nonsense corporate’ hat when you meant to wear your ‘quirky and kicked back’ hat? We’re not getting any younger, you know. Sooner or later you’re going to accidentally wear your court jester hat to the gynecologist and then where will you be? I’ll tell you where you’ll be. You’ll be in an undignified position and wearing a stupid hat is where you’ll be.

Resting bitch face. Hahahahaha. Just kidding. Wear that one all you want. Although, it wouldn’t hurt if every once in a while, you had a welcoming and kind look on your face. At least that’s what I hear from other people.

There isn’t anything wrong with getting advice about updating your look or what to wear, but we are just inundated with that shit, aren’t we?

Who says what is appropriate? From where I sit, it seems ‘appropriate’ changes based on geography, social status, income and size. After a while, the advice becomes a confusing blur. I think I’ll just keep wearing my Keds and jeans and black tee shirts.

Oh, I do have one real tip. Stop wearing holiday theme clothes. Seriously.





188 Thoughts.

  1. Do I have to wait until I am 50? I think Australia is slimming and eye liner looks fabulous when applied directly with a spatula. I prefer my magician’s hat at the gyno becuase, you know, magical vagina.

  2. This is terrific! Seriously, something actually useful for us to think about as we age. I seem to remember my Grandmother telling me that when she turned 50 she started doing what she wanted to do, stopped caring what everyone else thought, and spoke her mind. I’m pretty sure she told me that’s when she started swearing, too. 😀

  3. One of my favorite lines ever – “dick punch reality into submission”. I find the older I get the less I worry about what other people think. It’s very liberating.

    Jeans with holes – check. Luridly colored sneakers – check. Sleeveless shirts – ch… well no.

    I had a friend, one year younger than me, tell me that I am too old to wear my hair long. My answer to that – hair almost to my waist. It’s got gray streaks, that I can so far pass off as blonde highlights, but it’s long and it’s mine.

    • Had this discussion recently on FBook- I have a friend who’s always telling me to cut my hair. I am 62, and the answer is Noooooo!!! (Damn sticky keyboards.) Older women can rock anything, anytime, anywhere. Rock long gray hair if you want. I have not gone ‘natural’ yet, and still color my hair. I also wear sleeveless all the time, because I work out. With a nod to Oprah, who says ‘Nein’, I even wave goodbye in a sleeveless shirt.

      Stilettos, ballet flats, cowboy boots, leggings, wear whatever you want. The only thing I’ve drawn the line at is tube tops. Even a little wrinkled cleavage is all good. I cannot unsee some of the things women of all ages wear, and when I see a gut the size of Cleveland hanging over a bikini bottom, I have to wonder why I would ever worry.
      Don’t want to be a comment and blog link hog, so I’ll just read for awhile and try to keep my mouth shut:
      Some eighty or ninety year old woman should chime in here, and call all of us wussies-

  4. I refuse to give up my liquid black eyeliner and love my dark glasses. And we alk know that while smiling gives you wrinkles, resting bitch face keeps you pretty. (I googled it and it’s true. )

  5. Here’s another thing no woman over fifty should wear: an unappreciative spouse. It’s not support garment. It’s an accessory and doesn’t go with anything you’re wearing. Take that thing to Goodwill and leave it, then go shopping and try on Micronesia. After all that’s a country where it’s illegal to wear a necktie. Neckties are just wrong, with some exceptions. Diane Keaton wore one well in ‘Annie Hall’. And a hat too. And why did she wear it well? Because she didn’t give a shit. She wanted to dress like a disheveled fin de siecle Bohemian in Paris in August regardless of what anyone thought. And she wasn’t anywhere near fifty at the time.

  6. “dick punch reality into submission” is my favorite line in this post. This made me laugh out loud. You are so right that as women we have to deal with too much bullshit. I love all of the advice you give, it’s touching and hilarious at the same time.

  7. Love this. I’m not good at hats either. My hair is so thin and baby fine, I end up looking like I’m bald when I wear a hat. And I stopped reading women’s “self help” magazines long ago because I’d get so stressed out when on one page they’d advise to do THIS and on the very next page they’d advise to do THAT. Make up your damn mind, stupid magazine! Of course then you realize they don’t know shit and you should quit trying to garner advice from magazines. 🙂

  8. I guess being a guy over 50 I really don’t care what I wear or what people think. at the end of the day, I don’t go home to random people so who cares what they think. Thanks for the great advice.

  9. This isn’t just good advice for people over 50. This is really GREAT advice for everyone! And you do it in such a sophisticated and elegant way…. hahahahahaha I didn’t mean that. You do it in a way people are going to fucking listen!

  10. LOVE LOVE Keds. My husband used to hide them from me!
    He called them “town hen” shoes. We live in a small southern town and keds are standard attire. If I were a brave woman… I would sport Keds, Yoga pants and an offensively large t shirt – EVERY DAY. But I do have a dress code at work but you can believe within 5 minutes of entering my house… that is what I look like 🙂

  11. BWAHAHAHA!! Oh I love this so so much Michelle!! YES! I would actually like to add the greatest piece of wardrobe the 50+ women deserve to have on at ALL times…


    I’m nearing fifty at the ripe young age of 47, and I am finding that all those insecurities and demons of the past start to lose their grip in the fight for peace. Age does that. It examines those parts of our lives and ourselves and makes peace with it all. Acceptance rears it’s beautiful head as we lean more toward WHO we are rather than what we long to be. It’s really empowering, this aging process.

    I’ll keep wearing my sweats, fleece and sweaters from the thrift store. And I’ll sport them with pride, cause I’m worthy dammit.

  12. I was like, No! Don’t take resting bitch face away from me! It’s been my trademark since long before it was a thing, and it’s an introvert’s best defense against intrusion!

    This is a brilliant piece! We need to collectively throw away all of our f*cks and do as we please (I’m including 40-somethings here, too). There is a 70-year-old lady in our neighborhood who walks around in one of those old school terrycloth tube top jumpers, blond beehive, and bright pink lipstick. I totally want to be her when I grow up.

  13. You know somewhere behind the middle-aged, crazy-ass woman there really is a genius! I absolutely love this. This needs to win some sort of award or some such shit! I really can’t wait to meet you next month!

  14. Ugh. All of the above. You should see my resting face. Especially when I’m practising my cello. Because who doesn’t need a new challenge to add to all of our old ones at our age . . .

  15. Whoo, you scared me at first. I thought:
    “Oh no, there’s stuff I shouldn’t be wearing? And I’m turning 65 in two days? Holy crap.”
    Then, of course, you came through.
    Weirdly, I’ve always loved braids.
    I’ve got long grey hair (proudly deserved, I might add), and I finally got the guts to wear it in braids whenever I feel like it – especially in Yoga classes because a ponytail hurts the head during Savasana.
    At any rate, several compliments from perfect strangers ensued. Totally shocking.
    Any of you out there with long hair? Go for the braids, you’ll be surprised.
    ……Now I’m going to Google ‘theme clothes’.

    • Yeah, me too on the 65 and long hair. When I was younger, my hair reached the back of my knees and was really thick. Today it only comes to my waist & there is half as much – how do you tie them off? They’re so thin now that I’d have to staple them to keep them from un-braiding!

      • The trick is to not braid them all the way to the end. I do not have thick hair, and I use regular ponytail bands, and wrap them around a zillion times. Good luck! 🙂

        • I used to bitch about it too, because it literally took 24 hours to dry (I used my head as a roller to keep the frizz to a minimum). Now it’s thin & flat and much shorter and too hard to set. So, of course I live in South Florida so the only thing it can to is frizz! This is one of those things I think about when trying to “lose” – To cut or not to cut – and everyone knows that after a major cut you HATE your hair and can’t wait for it to grow out again! What to do – what to do…….

  16. Love it, Michelle! “…dick punch reality into submission.” Now there’s some solid advice you won’t find in any fashion mag or site HA! <3 I will say though—please stop wearing shants. A cross between shorts and pants don't help us in any way, especially the ones with the strings hanging off the bottom.

  17. I have never understood what makes these experts an expert on something they have no experience with. You are the only woman over 50 I have ever seen come out with a list of what not to wear when you are a woman over 50 – AND YOU NAILED IT. Especially the part about “dick punch reality into submission” – that is pure gold.

    This needs to be on Huffington. How do we get this on Huffington?

  18. Wow! Such a great post.

    I have lost the hats, wear jeans (and the occasional PRINCE t-shirt) all the time, and although I don’t wear the weight of the world, I do tend to wear the weight and woes of others….I will scale that back….I love the idea of just a small continent…or maybe I will try on the continent of Iwillcarealittlelessia
    I hear that looks great from behind!

  19. LOVE THIS !!!!! I realised the other day that I am old. We were working in the garden and needed something from the hardware store. Given we live a little in the sticks, we just hopped in the car and set off. We got to Bunnings and I realised we had just gone out in our gardening clothes, hair throw up in a messy pony, no make up, stinky – and I didn’t even care if I bumped into anyone !!! Then I realised I had come of age – finally ! LOL
    Have the best weekend (when it gets to you !!!) xox

  20. To all the ladies in this thread of comments who have grey hair or are going grey- Don’t feel like grey hair means you need to wear it short! I LOVE seeing women with long grey hair. Its so unusual since everyone seems to chop it off when it changes color, and there are so many beautiful shades we’re missing out on.

    -signed a 34 year old brunette who will probably go fantastically, amazingly grey the day she turns 50

    To Michelle- I love this whole list and we should all be following these rules at any age! Fuck yes!

  21. I end having far more respect for those who rock their own style than go with what society deems “appropriate for their age.” Sure it’s a little questionable when a 45 year old woman attempts to dress like she’s 25 with her boobs hanging out everywhere but who the fuck are we to judge? If a woman over 50 wants to rock a purple tutu and bright pink hair (for example) then I say go on with your bad self.

    I totally agree with this list though. Who needs extra weight in their heart and minds over shit that happened three decades ago? Move on and be happy. We deserve it!

  22. Excellent. Despite being well into my dotage, I was able to follow the whole thought train, until the very end, when I realized I don’t know what theme clothes are.

      • Great. I appreciate it. I am happy to report I have nothing to worry about except a warm jacket with a little Corgi on the pocket. I’m not getting rid of it. It will look nice with black eyeliner.

  23. Dude, i am days from hitting the dreaded milestone, so this comes just in time. This is excellent. Love your style. And thank God I can take the weight of the world off my shoulders because I’ve pretty much already sent one of my chiropractor’s kids to college already.

  24. Michelle, you are all that is keeping me and my introverted, resting b—h face sane. Please never stop.
    Also, I am 71 and recently lost 20 pounds and really want to wear leggings. Don’t I deserve that?

  25. (for those few of us, in this Comment section, who hail from Y Chromia),
    old dudes:
    * try to remember that having a lot of pockets in that All Weather London Fog jacket is not a good enough reason to wear it in public (even if it means you have a place for that little notebook you carry everywhere)
    * no… socks-with-sandals is *not* the same as sandals
    * belts are meant to fit comfortably at the top of the hips, not just-under-the-man-tits
    * zippers are still you friend… do not forget them
    and last, but not least, …when you’re out there with your buddy in the mall… not only can they hear you whisper (from 100 feet away) but they can see you too

    ..wait, that last? I take it back…. you’re over 50! go ahead and stare and shout funny asides to your friend…. what, are they gonna refuse to go to the prom with you?

    hey Michelle!! you are one of my fuckin favorite bloggerinae

  26. I just stumbled upon your blog after reading this awesome article someone posted on Facebook. Right on Sister! I sucked in air when I read the line that there really were some things 50+’s shouldn’t wear (what?! Noooo and this article was going so well). But then was delighted as I read on, shaking my head in agreement. Thanks for an intelligent and funny article. Not sure I’m ready to give up my resting bitch face just yet though!

  27. Dick punch. Tee Hee.

    Ok, this was brilliant, because I saw that damn Facebook article about what we shouldn’t wear after 50. Screw them and the horse they rode in on! If you’ve got it, flaunt it, whatever ‘it’ is! 🙂

  28. Ok came to read what was so bad that someone was offended but what the hell nothing here who gives a flying fuck if you use that word “flying” oh no it’s the word “fuck” that people are offended by well grow the fuck up, if you don’t like the word or the language then go some place else no one is making anyone read anything.

  29. I fucking LOVE this post! Screw the fucking rules – one should know by now what articles of clothing one looks ridiculous/slutty in so either OWN that shit, or stop wearing it. I am not quite 50 but am quickly approaching… rules are for lemmings. 50 is the time to have your own mind and WEAR it LOUD & PROUD! 😀

  30. I agree about not wearing too many hats — but I wish I could wear one hat, sometimes. My daughter looks fabulous in any hat — a jaunty bowler, a sexy beret — she can pull any of them off. I just look like an idiot. PS, I’ve always wanted to visit Michelloponia!

  31. I may or may not have done the Jersey Shore Fist Pump while reading this article even though I’m too old to watch reality tv on MTV or whatever network it was/is on. I know nothing about Jersey Shores. Delete this comment.

    You make me laugh, and I’m not mad about that.

  32. This is a hoot! As an over 50, I can tell you I absolutely agree with your “rules”, which, by the way are not rules at all, because those of us who are over 50 don’t abide by rules anyway!

  33. Well, I can surely see why this post got so much attention!! BRILLIANT!

    Oh this is good. SO good.

    I’m not yet 50. I have two years to go.

    So I’m still gonna wear my holiday themed outfits.


  34. Clearly I like to read the 50+ “don’ts” for entertainment. I find it extremely funny that someone probably in their 30’s is writing them. Too many rules. Wear what makes you feel good! Be who you are.

  35. You so had me at dick punch reality….gotta remember that one. First timer here, but gonna be a lifer with you. Thanks for the yucks.

  36. Just found this blog and I love, love this post. . . “shame and regret are especially hard to wear after fifty”. . . It sure is, and regret just does not look on everybody!! I’m on the other side of sixty and wear what I want with reckless abandon. I just bookmarked this blog and will be back to read more. . .THANKS!

  37. Ok, so I figure it’s none of my business what other people think of me. So I don’t give a shit. I wear leggins, bikini’s, get a brazilian wax cuz you never know when you might meet someone thirty who thinks your hot as hell, and I’m not saying no. Gonna hit that..
    And, well a host of other inappropriate shit, my mother would say. I love this article and I have subscribed and I will have so so much to add.

  38. Lmao! Brilliant, just brilliant! Made my Friday – especially “Sooner or later you’re going to accidentally wear your court jester hat to the gynecologist and then where will you be?”!

  39. recently found this as a post on face book and shared it with many of my over 50 friends. For those of us who embrace our own ‘fuck what other people think” attitudes, it was a delightful read. My 23 year old cool as hell daughter did have one comment about holiday attire, She states that it should only be worn ironically…

  40. I read your column on Piniterest describing what women in their mid-life crisis should’t wear. I write a blog to a transgender site mostly to help the older girls with clothing decisions. I thought your column was very appropo, as by nature of their status most of them, including me, have many worries and conceerns mostly brought on by society. So I wondered if you wouldn’t mind if I borrowed from it? Thank you for the column

  41. I wish this advice was printed on a business card so that I could carry it around with me to remind myself. Of course, the print would be so small that I wouldn’t be able to read it, but I’d know!
    Thank you!

  42. Very well said.. made me laugh my ass off..even got my hubby laughing..
    In this unusually sick world, sometimes you need a great laugh.. i take all i can get.
    Thank you

  43. Very good. I don’t think I’ve ever written to anyone about an article that they wrote .This is my first time and I’ll tell you what it really struck a chord ,you are right on girl!!!

  44. Yes, Yes and YES!!! Perfect article. We’ve gotten through enough by now to let someone dictate what to wear for pity sake. Wear what you want and let it speak your soul. Sometimes I wear clothes to hide and sometimes I wear them to shine. It depends on my mood.Thank you for your eloquent words. 6 years after you wrote this ( according to the date I see on the article) and COVID, loss and uncertainty seem to entrench us into darkness. It’s nice to read something that liberates that feeling of being trapped and sad.

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