It Might Not Be What You Think - This post will really surprise you if you are used to all the negativity of life after 50. | 50 plus | menopause | aging | fashion over 50 | second act | #aging #midlife
The Second Act

What Not To Wear After Age 50 – It Might Not Be What You Think

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 body”.

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I want to point out to the writer who wrote the ‘no-no’ article, you need to remember you are writing for women after the age of 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 after age 50 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 f*ck’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 eyeliner. I say give up wearing shame and regret and fuck giving up on black eyeliner.

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, but 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-themed clothes after the age of 50. Seriously.

Originally posted on Rubber Shoes In Hell by @RageMichelle

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Please drop a comment below to let us know what you think.


  • Shirley

    Hello Aileen, I really appreciate you for your blog. You have shared such a great tips. I will suggest all the women that they should follow your tips. Thanks for sharing this amazing blog.

    • Two Southern Sweeties

      Good morning Shirley! I’m glad that you are enjoying our blog.

      I did want to let you know that Aileen has not really been involved with the blog for several years now, however, I’m sure she still wishes the best for all of our friends and followers.

      Make it a great day!


  • MMJ Canada

    Hi Aileen! Great blog, find it entertaining and helpful. Thank you for the advise and this is my personal favorite, let me quote, “When you wear the weight of the world on your shoulders, you age. “

  • Kathleen

    I love your articles..I am extremely moved that someone ,someplace has 20/20 vision and treats women of my age(over 70)as real people!Thank you for that!

  • Analy Sanchez

    I so love all your articles. I look forward to receiving them, even the recipe ones, I don’t really cook anymore, nevertheless, fin to read. I’m Cuban Country lady myself and love all the southern Do’s and don’t”s, in my culture we have a lot of the same, raised in the city, but always a country girl at heart, moved as soon as I could, I live in a small town on a beautiful ranch, wouldn’t trade it for the world.
    ExceLlent reads🤗

    • Two Southern Sweeties

      It is always great to hear from our friends. Thank you so much for sharing and for leaving such wonderful feedback. I personally could never live in the city again, I’m a country girl now.

      Make it a great day!

  • Pat

    “When you’re 20 you care what everyone thinks. When you’re 40 you stop caring what everyone thinks. When you’re 60 you realize no one was ever thinking about you in the first place.” ― Winston S. Churchill

    Loved your article! One more point; when you’re over 50 you can still be 32 in your mind and do what ever you damn well please!

  • I. W.

    “What not to wear after 50”
    I suppose I might have found some humor in this article but when I came
    across the supposedly bleeped “F…k” work, that floored me. Then on in the
    article the usage of the word applied to women as “b.tch” work and later, the
    “sh-t” word.. I am sorry. I just do not use that kind of language and so, I just
    stopped reading. If a person wants to swear/cursef on their own time and in
    ‘their own space, that is up to them. However, when posting for the world to
    see and read, that person assumes that all people speak that way. Vularity is
    not acceptable to all who read your articles. I just found this site and subscribed.
    You have great recipes and articles.
    I would imagine that your posts allow such or you would have warned against
    using profanity, etc. I am sorry. I realize that I am only one person and maybe
    the only person who has commented on this topic.
    Thanks for hearing me out.
    I. W.

  • Esmè

    I am 75 this February and would love to see more of what to wear. I am throwing out a lot of old cloths and trying to wear less is more. I am tall dark hair ,brown eyes,hardly any grey hair and can wear bright colors and soft print. No beige for me please. Would love to hear from you . Thanking you. Esmè

    • Two Southern Sweeties

      Hi Esme
      Take a look at our Pinterest board “Fashion Over 50”. You may get some ideas from there. I have a lot of great pins for outfits and how to put things together.
      I personally believe everyone should wear whatever makes them feel happy and beautiful.
      Make it a great day!

  • Ashley Hudson

    A great read; thank you. Brought back memories of when I started to get gray hair and was going to cut it. My husband did not want me to cut it and asked me to wear it natural and long. At that time it was common practice for women to cut their hair short and color out the gray because of being older. Men and woman alike have admired my long, gray hair over the years and still do so. Many men say that they wish their wives would have their hair long and natural and not “mun” styles. I am so thankful for my husband’s request to leave my hair long and natural and very happy to now be seeing it more often. I am now well over the age of 50; my hair still long and gray and still receive many compliments from both men and women.

  • Susan


    Thank you so much for this article. Its the best laugh I’ve had in ages and oh so true. Too many of us women wear and carry far too much crap around without realising it. I’m 64 now and my motto is
    Just do it! Life is too short to stress and worry about stupid things that aren’t important. Its so liberating to just do it and enjoy life while you can!

    Good luck ladies, live your best life now!

  • Jessika

    I’m earthy. Worked in a Police Dept as a secretary, and hospitals as a RN. Language doesn’t offend me, sometimes those are the only words that fit the situation and our frustration with it. I’m offended by articles referring to me by my age, what I should be wearing, how to wear my hair and what length to wear it, what I should be doing and thinking. These articles are condescending and an insult to my years, my life experience and my intellect.

    I loved this article; thank you for speaking to me like an adult and not calling me ‘honey’!

  • Gillian F

    Thank you. Last night I dumped d off a list similar to your article. Apparently elegance as defined by the owner is someone who blends into the woodwork wearing boring neutrals. I wrote a note back expressing my idea of what she was preaching. 73. I wore uniforms My other clothing was’s so I chose it carefully. Clothing is costume. It tells the world who we are. I was bono Romanticand ethnic Goth for many decades. My clothing choices reflect that.And I get stopped by complete strangers who compliment me. I am not a,Church Lady nor am I someone who wants to be indistinguishable from.the woodwork. And my husband(7 years younger) loves it.
    I don’t know why these women believe they know what is right for everyone else, but their condescending arrogance possesses off.

    • Two Southern Sweeties

      Hey Gillian.
      Good for you!!! It is so important to be the person “you” love. I believe it is important to no longer let society tell us how we are supposed to look based on their sometimes warped sense of what “old” is.

  • Gillian

    Thank you.
    If I followed the “rules” in all those articles, I could only wear a burnpqa or human with a face veil.and an abayah, because those lists contradict themselves. I never looked very good in tailored suits or Mommy dresses. I only wore them if my job required them. I hated preppy clothes too.

    Where were you two when I lived in the Atlanta suburbs and got glares if I wore anything even vaguely revealing?

  • Zoe Owen

    I am so fed up with people saying ‘accept the grey’, ‘you have to accept your age and enjoy it’ I do, I do, I love being where I am and having grown up kids and grandchildren, but does that mean I can’t go crazy with my hair. I have been brown, ginger, red, and blonde. I get bored with grey sometimes. I’m seeing my daughter next week, she has pink hair just now, and I’m going to be red, so there. This is from a 73 year old hippie/ designer/ artist. Enjoy yourself

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