Do You Blindly Follow Over 40 Fashion Rules?

Do you blindly follow fashion rules related to age, or do you dress outside the box? I still find many women still live by outdated style rules that keep them from looking Age-Amazing. They say rules were meant to be broken, and I often have to agree when it comes to over 40 fashion rules. Here’s what I mean about fashion rules to break.

Imagine if we all blindly followed over 40 fashion rules? That would mean…

No Short Skirts

Technically, Jennifer Aniston should have stopped wearing short skirts, especially minis, at 40, but she’s 49 now and still wearing them with no problem. She takes excellent care of herself, works out, and has legs that look better than many women in their 20s, so on the red carpet and off, she wears very short skirts.

I think she still looks pretty darn fabulous. What do you think? It’s all part of her sporty style. Is it right or wrong to wear a short skirt at her age? How fast is too short?

Jennifer Aniston Mini skirt


No Cleavage Allowed

If Oprah (64)  followed the traditional fashion rules for mature women, she shouldn’t wear low-cut dresses that exposed cleavage. That’s supposed to be for the younger gals only…or is it?

That’s quite the dress, and she has a total bust, but I think she’s rocking it! What’s your opinion? Can Oprah look that sexy, or should she be “dressing age appropriately?”

Oprah winfrey big glases

Bikinis Banned

Most women think it’s time to hang up the bikini at 40, but Helen Mirren is 72! Helen is one hot boomer babe who is not afraid to let it all hang out at the beach.

Would you wear a bikini? Do you think automatically thinking a one-piece is in order when you turn 40, old-fashioned, outdated, or simply appropriate?

helen mirren bikini

Skip Spaghetti Straps

If everyone followed fashion rules, Lauren Hutton (age 61 in this photo, and now age 74) should stay away from spaghetti straps for twenty-somethings, or so we have been told.

Do the thickness of your straps matter if you feel confident in this style? I don’t think so. 


lauren hutton

Say Goodbye to Long Hair

Have you often heard that it’s time to give up long hair once you hit 40? ..that it doesn’t look age-appropriate? If everyone followed fashion rules, no woman over 40 should have hair past their shoulders.

I’m afraid I have to disagree with that. I think any woman would die to have hair like Brooke Shields in her 50s. What do you think?


Brooke shields

Lay Off Black Leather 

Is leather, and especially black leather, silly over 40? Jane Seymour can still rock it, and she’s 67! If you like and style it right, it can add a youthful, edgy touch.

But I’d love you to weigh in. Is no leather at 67 a style rule meant to be broken, or should Jane be following?

jane seymour black leather jacket


I hope these examples have got you thinking. Can you see the point I am making? I can give you dressing guidelines for what works well for most women at a certain age, but in the end, if you have the right body and attitude, you can look fabulous in just about anything at any age.

Try some things on. Be sure to have a full-length mirror on hand. Listen to your gut and let it be the judge. Be honest and trustworthy with your style! Know the rules, but be prepared to break them.

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22 thoughts on “Do You Blindly Follow Over 40 Fashion Rules?

  1. The examples you provided are not relevant to regular people. Celebrities have extensive surgeries to look youthful. There are procedures to lift baggy knees and reduce belly fat. There are cosmetic procedures for everything! They have personal trainers to keep them in great shape. They are more significant than life.
    They are “gorgeous” no matter what they wear. I don’t follow fashion trends; I wear what I think looks good on me. I don’t think it appropriate to show cleavage or wear a mini skirt after 40.

  2. What is the rationale behind these rules, that you look older for not following them? That the look of older flesh will offend people? I follow some of These rules because I’m fat and have horrible cellulite. I’ve never worn a mini at any age, not when I was young because of KP, and not now in mid-age because of cellulite. I don’t wear bikinis either. I have long hair, cleavage when appropriate, and black rock leather. I think these rules apply only to middle-aged women who are dumb. Wear what flatters you. Don’t dress like a teenager or a hooker. These are the rules I follow.

  3. My first thoughts were, how much photoshopped was there in the photographs of the celebrities?! The message here is that if you still have fabulous eggs, wrinkle-free cleavage, great figure, etc., then show it off whatever age you are, but cover up more if they are not your best feature. That also goes for any period, in my opinion.

  4. I am happy to see some of these broken. Being petite, I think skirts and dresses look better a little more up the leg than the knee on us Petites if you got the legs. I try to stay with a nude pump that the vamp is low cut. I don’t go short but not to the knee all the time—the bikini thing I do too. Self-tanner is a must for me. While on vacation last year, I got a cute one-piece that was on sale. I love black leather jackets over a softer blouse to balance the look. Long hair should be worn if that’s your best look, not your age. I have short, naturally curly hair since I just got curly in the last two years. And love having curl even though straight is the style. I can still blow dry straight with a round brush too. My best friend wears hers to the shoulders and looks great! Thanks for reminding us that the guidelines or rules aren’t in stone, and this modern world has changed from strict rules to follow.

  5. Greetings Deborah,

    Just passing through…..

    As a man who is 60 y/o, I am glad you focus on good judgment in dressing rather than blind fashion. I still pick up select items from young men’s sections. But whatever articles of clothing I buy, I ask myself, “does this do anything for me?”

    Experience has taught me that for some bizarre reason, clothes frequently look better in the fitting room than they do after you bring them home. Another thing I find is that most fitting rooms are too built too small to get a perspective of whatever clothing item one is trying. I find stepping outside the fitting room in a full-length mirror (or three, you know what I am talking about) in which you can see how the garment fits and looks on you from a few feet away (and up close too) is most helpful in making a selection. Unusual for a guy, but I am obsessed with clothes and love to shop. Good taste is always age-appropriate and a reflection of one’s judgment. Of course, all of us can go wrong once in a while, as is evident on the academy awards red carpet.

    Thank you for a delightful and lively blog.

    Salutations to the women of the world.


  6. Hi Deborah,

    I’m so happy to read all the excellent advice about fashion. I’m already on my 52, but I don’t know if I still look good and have good taste in clothing. Lately, I feel confused because I still don’t know how to dress for my age. I read, dress how you think, and I am still confused. I hope you can give me advice on how to dress. Maria

  7. Hi Deborah,
    Speaking as a 40-something man I think of the “rules” more as guidelines. They’re a good starting point but I’m not afraid to break them for the sake of real style

  8. At our age, it’s all about self-expression. Fashion should be all about our unique style! Yes to spaghetti straps and yes to long hair!!

    love your blog,

  9. I agree! Now is when we are more in tune with our inner style, and it’s time to experiment with our looks to find what expresses us best. The goal is not to look like our daughters or mothers but to look like our best selves…it can be very empowering.

    1. Hi Nancy,
      The point you are making is sure actual!
      We need to look in the mirror and ask ourselves, how do I look? If you think you are dressing too sexy, you probably are, and if you feel too old you probably are. Our “gut” does not lie!

  10. Fashion guidelines are probably better to say. And I think this article proves that fashion should be as body appropriate as age appropriate. I’m almost 47 but am routinely mistaken for being 30. That being the case, I can wear many “youthful” things and others I never would—no bathing suits, mini skirts, spaghetti straps, girly puffy sleeves, ruffles, or bows. However, I flaunt my cleavage all night long, have long hair, live in jeans (only the latest and greatest), and big earrings.

    1. Hi Sage Goddess,
      Your style sounds right on! Check out my article on how to break “the rules,” too! We like the word “guidelines,” too…I certainly am not here to be the fashion police!!! I want to show all sorts of examples and let you take it from there!

  11. In her book Manifesto of Style, Danielle LaPorte says, “Style matters. The design of your life can inspire you or more you. Every aesthetic and material choice sends a message to the world about who you are, and the world responds accordingly.” Wear what you want. (But stay away from front-pleated pants and too-tight t-shirts)Classy, classic, and chic…

    1. Hi Delta, Yes, so true!!! After 40, we can start feeling more comfortable dressing how we want. However, many women fall into the trap of being stuck in a rut. Fashion can be a fun tool to keep looking fresh and youthful! You have a great point about sticking with classy, classy, and chic!

  12. Yes, yes, yes!!! I SO totally agree with you Deborahs with regard to fashion
    ‘rules’ for us over 40’s. Some rules are made to be broken & in all of the above pics these over 40 ladies absolutely rocked their look & broke the rules wonderfully. It’s such an individual thing. I went to my daughter’s 21st birthday recently in a black above the knee dress (I won’t say mini) & wore opaque tights with little suede high-heel ankle boots. Well let me tell you I couldn’t count the number of guests who couldn’t believe I was Tara’s mother – the general concensus was ‘you don’t look old enough’ or ‘wow you must have had her when you were young’. (No well not really, I was 24). It sure did my ego a lot of good & they can’t all have been ‘just being polite’ can they?? LOL Then again I wouldn’t go showing my upper arms with reckless abandon, but if you trust your gut you usually can’t go wrong. My favourite quote ‘Mutton dressed as lamb is not attractive, but mutton dressed as mutton is worse’….

It's your life. Make it Fabulous!

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