Home Uncategorized How to Dress Over 50 (and 10 things you should never wear!)

How to Dress Over 50 (and 10 things you should never wear!)

by Roberto
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You’re here because you’re either nearing 50, you are 50 or you’re over 50 and you have no clue what you should be wearing anymore. Like, is there a catalogue for age-appropriate clothes for 50-year-olds? Who knows.

Anyway, in this article, I’m going to tell you how to dress over 50 and share a list of things you should never wear.

Never ever. Never.

(this article contains affiliate links so if you make a purchase I may make a small commission-affiliate disclosure here)

How should a 50-year-old woman dress?

A lot of us have this question. I know I did. How should a 50-year-old woman dress? Where is that catalogue to order clothes from? We all remember the Sears and Eaton catalogues that used to come out every season. 

You know, the over 50 fashion catalogue. (hard eye roll here)

Remember that section for the older women or ‘old ladies’ as some would call us (like those 20-year-old brats)? As 20-year-olds we passed that section and went right to the trendy clothes.

But we’re not 20-year-olds anymore (insert crying emoji here).

Now before you get your high-cut briefs in a bunch, please know that when I use the term ‘old ladies’ I don’t really mean it. We’re not old dammit. We are F.I.N.E.

Anyway, I have a small confession to make.

Every now and then I sit and wonder if I’m one of those 50-year-old women who are desperately still trying to look 25. If you were to take a peek at my wardrobe you would think that a 25-year-old lived in my house.

Did I become one of those women? Uggggh!!! I used to point and laugh at them 25 years ago. Is there a 25-year-old somewhere out there pointing and laughing at me? (insert another crying emoji here).

But I feel I some got me some personal style. Know what I’m saying? I guess the best way to describe my style is ‘sassy flirty Iva style’. If that’s even a thing.

What women over 50 should wear?

I often wondered who the person was who decided that once you hit 50 there is a selection of age-appropriate clothes. “Oh I’m sorry, you just hit 50? Ok you can no longer shop in this section you must choose your wardrobe from that section waaaaaaaaay over there in the back corner. The section for mature women”.

That guy. Who’s that guy? Was it a guy? I’m sad if it was a woman who came up with this unwritten rule.

If you were to Google “clothes for women over 50”, wait, let me do that for you and show you what comes up.

Photo credit: glossyu.com

Ummmm…ah …..classic pieces, yes?…hard pass…

When I Googled, the images were all blazers, blouses, long pants, long skirts, and huge purses, I cringed. Hardcore. Now in Google’s defense, there were a few images that I actually liked.

I mean, minus the bag big enough to hide a small child in, I kinda like this look though I would never wear those shoes (ouch), but I could work this outfit.

I think this is a classic style (though I think I’d top it with a leather jacket and a tank top) and I love the straight-leg jeans with the small tear.

And then I found this cute little dress and high heels at Inspired Beauty I think this patterned dress would look smoking hot with some stylish boots (in neutral colors)!

Can you tell I’m not a long sleeve, white shirt, pencil skirt kinda gal? haha!!


Image courtesy of inspiredbeauty.com

And then this kinda hot little stylish outfit too! Those shoes look kinda comfy too.


Image courtesy of inspired-beauty.com

But the question here is all about how to dress over 50. I want to know why women over 50 should have to select their clothes from the senior line. Can someone help me with that, please?? (insert an angry emoji here)

Why is there a completely different fashion for women over 50 line anyway?

And then there’s me! The little fashion rebel. I’m a jeans, tank top, little black dress, flat fun shoes and the odd boho dress kinda gal. 

Nobody showed me how to dress over 50. I couldn’t find an instruction manual anywhere. And why did I have to change anything just because I got a little older?

“THEY” say, don’t wear your hair long, it ages you. Don’t wear short skirts, it makes you look like you’re trying to be 25 again. Stop trying to act and dress like younger women.

Don’t wear high heels, you look like a tired old hooker. Don’t wear eyeliner. Don’t wear pastel eye shadow, your fine lines are accentuated.

Don’t wear this, don’t wear that. They said!!! Don’t Don’t Don’t.

Who are they anyway?

You might also really like this fun article I wrote on painful sex after 50.

Painful Sex After 50-A Humorous Look at Menopause

How women over 50 should dress, act and look

Apparently, we’re supposed to look, dress and act our age. I don’t get it though. Why do we have to do that? And why are we frowned upon if we don’t do that?

Remember the 25-year-olds pointing and laughing? Ya, that. Suddenly we’re made fun of because we don’t know how to dress, act or look our age.

And it’s kinda uncomfortable.

So I found this chick on YouTube a while back while I was doing some competitor market research ( I need to keep an eye on these peeps) and she completely dispels any myths about how to look and how to dress over 50. I encourage you to check her out.

Yes, she’s my competition BUT she also truly is a sweet wonderful woman with tons of amazing videos that I’m happy to share with other women over 50. While I’m not a huge fan of all her fashion tips, she does have some pretty decent tips too though.

She shows you how to do makeup over 50, how to look 10 years younger, how to exercise over 50 and so much more! She also discusses things like:

  • what to wear at a special event
  • different ways to put together timeless pieces
  • things to wear to bring out your best features
  • some new looks for mature women
  • and so much more

Seriously, go check her out.

How to dress over 50 and overweight

Did you know there are fashion rules if you happen to be over 50 AND overweight? Oy. When did this happen? 

And let’s not forget there are fashion rules too if you’re height challenged. Yup. “They” will even show you how to dress over 50 and short. 


What not to wear after 50

I could write a full blog post on what not to wear after 50 but it sounds exhausting and pathetic if I’m honest. Why are there dressing rules? Why is there a special department just for us? But most importantly, what I want to know is, why are so many women shopping in this department and following society’s rules?

Do you want to know really how to dress over 50? Do you want to know what you really should not wear after 50? Do you want to know what this ‘age group’ should be wearing?

Buckle up, babe. Here it comes. Oh and by the way, throw your body type and body shape right out the window. None of that applies here 🙂 You’re gonna love these style tips.

Trust me on that!


It’s tough being a woman over 50

Being a woman is hard. Teenage years are hard and confusing, then you’re trying to find your way in your 20’s and 30’s, the 40’s come and you feel like you might be missing something and then suddenly you’re 50 and “they” want to tell you how to dress over 50. 

You know. Because you’re special and different and old something ridiculous like that. Oh we’re special alright! I’ll give ya that.

So you need to know I’m a bit of a rebel but not in a bad way. I dance to the beat of my own drum. I throw caution to the wind. I don’t follow rules (often) especially NOT fashion rules and I firmly believe that your life is what you make it and people will treat you according to how you present yourself to them.

Why am I telling you all this?

Because being a woman is hard. We’re already up against so many challenges and for years we are supposed to act and behave a certain way. And we have for the most part. Not all of us. But many of us.

When I hit 50 I tossed out all the rules, stopped listening to and following the masses, and stepped into my own personal power. It was exhilarating, liberating, and effin beautiful.

I found my vibe, dumped my old tribe and my old life, found my voice (and used it ALOT), and started really loving and embracing life. When they say life begins at 50 they mean it. And I get it. I totally get it.

Without further ado, here are some helpful tips…

How to dress over 50 – 10 things you should never wear

1 The opinion of others

Can you live your life for yourself, please? Does it matter what others think of you? Most of them don’t even think highly of themselves. Let them point, stare and whisper, I say. Give them something to talk about, I say!

You should never wear the opinion of others. Ever. 

2 Baggage from the past

Drop all the big ugly heavy bags. They don’t look good on you. They are weighing you down and, if I might add, aging you quickly. Do yourself a favour, and get rid of all your emotional baggage. We’re moving forward in life, not backward. None of the stuff from yesterday matters today or tomorrow.

3 Jealousy

So Margaret looks good for her age and “you’d never know she was a day over 50!” they say. Who cares? Good for Margaret. She’s beautiful and you know what, so are you! There’s no need to be jealous of other women. We’re all beautiful and amazing in our own unique ways.

4 Fear of getting old

Yes, we’re getting older. Life goes on. We’re not 25 anymore. But life is what you make it. You’re not dead yet and you have no idea when you will die. Live it up now babe. Time’s flying by! Do things you always wanted to do, try new things, travel, and live out loud.

5 The doormat

Seriously, stop wearing (or being) the doormat. You’ve worn it for far too long. You are no one’s b****. Find your voice, start using and start saying NO to all these people who have been taking advantage of you all this time. Tell more people to f off!!

6 Cattiness

Time to grow up. We’re not in high school anymore and besides, that catty look looks horrible on you. Disgusting if you will. Life isn’t a competition. We’re all in this together. Put your pointy finger down and stand tall with your sisters! Lift a sister up, don’t put her down. The world is already a heavy place to be in.

7 Judgement

If you’re still judging others, stop it. You are no better than anyone else and no one is better than you. Judging others makes you ugly no matter how beautiful you are on the outside. In case you missed the memo, your poop stinks just as much as the next guy’s.

8 Regret

Like baggage, regret also ages you. So you didn’t do this or that, so you never told so and so something, so you never went to that place. So what? Regret does nothing to enhance your life and only makes you sad and miserable. Dump it.

9 Crocs

Burn them. Have a croc destroying party. Donate them if you want but get rid of them!!

Haha I’m kidding. Girl we need comfy shoes. I feel ya. For me, the perfect shoe is a pair of flip flops. I own way too many and I love each pair.

But listen, you can wear crocs all you want. (insert cute emoji here)

10 Worry

It’s time to turn that worry frown upside down and make it a smile. Life is short and we’re over halfway through our lives. There’s no time to worry or hold back or not live the life you deserve and desire. Smile at strangers, eat the cake, go to foreign lands, say hi to the cute boy….go do things and stop worrying if it’s right or wrong or if people will talk.

If it makes you happy, it’s right.


Forget age appropriate clothing

So here’s the good news.

How about you just forget your age? Wear what you want, do what you want, say, and be what you want. Girl, if you wanna wear skinny jeans, tank tops, and leather jackets, please do!!

If you wanna wear that little black dress and ankle boots, do that too! Love bright colors? Good. Wear those too!

You wanna look like you’re ready for the red carpet wearing some hot Ralph Lauren number? You do you, babe!!

And then take pictures of your hot signature style and be proud of the skin you’re in and the style you have!!!

I think the best thing about being a mature woman is that at this point, we just don’t care. We’ll wear crop tops and an animal print, we’ll wear short shorts and our daughter’s jeans.

We just don’t care.

What Should a Woman Over 50 Wear?

Whatever the eff you want!!!!!! Whether you’re a woman over 50 or a woman over 60 or heck, even 70 or 80!!!

You must always remember this is your life and no one on the planet can tell you how to live it or what you should wear while you’re living it.

Be the best version of yourself that you can be! Get the heck out of your comfort zone.

So forget age appropriate clothing, forget all the rules for women over 50 about how we should act, look and talk. Just do you babe.

ox iva xo

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