Fun with Over 50 Fashion: 5 Timeless Tricks

Fashion fun for Over 50s

Has your fashion fun faded now that you are dealing with over 50 fashion? What if it didn’t have to? 

Remember how it felt to lie in bed and browse fashion magazines when you were younger? Or the thrill of wearing something that makes you feel amazing? 

What about having a stranger stop you to compliment your outfit? That’s fun, right? 

But often as we age, we don the boring over 50 fashion uniform.  And what does that say about our lives? If we look and dress like a stereotype, then that’s what our lives will be – not much fun at all. 

But here’s the thing…

Your clothes can have a big impact on your confidence level.  And here’s some good news…you can have much more fashion fun over 50 than you could in your teenage years. 

Here are 5 tricks on how to do it from an over 50 fashionista.

Your shape has changed. Embrace it.

Of course I wish I had the body I had at 20. (Yes, the one that I didn’t appreciate nearly enough at the time!) Hormones naturally shift as we age, which has an impact on our shape. It’s inevitable that most of us wind up with more of an “apple” or “pear” shape and much larger than we were when we were younger. 

So, what? Embrace it. 

Acknowledging your shape change allows you to choose clothing that works with your body rather than making you feel like you don’t fit.  If you’ve ever tried on clothes and left a dressing room frustrated, chances are you don’t yet know how to dress for your current shape. 

Start choosing pieces of clothing that work for your real, current body type. For example, “apple” shapes can “fake a waist” with a wide belt under a jacket.  It’s a game-changer! Pears can use wide and short necklines to give the visual illusion of shoulders that balance wide hips and thighs.

There are great resources out there for learning to dress for your body shape. These are some of my favorites. 

Quit feeling like you are the “wrong” shape. You are exactly right for where you are right now. Own it and turn fashion into fun while learning simple tips to dress it!

Example of cinching in a belt to create a waist
Patricia and Cathy wearing wide belts

Thrift Shopping Gives you an Edge in Over 50 Fashion.

One of the best ways to test drive new clothing styles is by shopping at thrift stores or charity shops. It’s not just for people who have limited budgets, although it does help you cut your costs. And if you feel queasy about second hand clothing, try vintage clothing, which has a different vibe and may well be better quality.  You can get great bargains in any of them. But there’s a trick to it.

Ignore the sizes. 

Sizes can vary ridiculously from brand to brand–to the point that they become irrelevant, so you have to learn to eyeball it or bring a tape measure. 

Take your best fitting pair of pants/trousers (or skirt, or shirt, or jacket) and physically measure them.  That’s your real size, and you can browse the racks (which might be in disarray anyway) finding what catches your eye with its shape and fit.

Off the rack retail never fits as well as purchasing something that is not quite right (on the cheap) and taking it to a tailor. Adjusting hems, sleeves, or waists is rarely expensive and you can create something that is a perfect fit just for you.

Test drive your new look on the cheap 

The other advantage to thrift stores? You can test drive a new look without much investment and always just re-donate if you don’t absolutely love it. 

Here’s another tip when trying on thrift store clothes at home: get a tripod for your phone and take selfies. The camera gives WAY more accurate feedback than the mirror. Lower the camera to take a photo straight on, and you can see how an outfit is working with your shape.  Try on all sorts of styles, shapes and looks, and use the visual feedback from the photographs to teach yourself which shapes make you feel a million dollars.  Ditch the rest.

Tweaks like pushing up sleeves, changing the hem on a skirt, adding a belt or a scarf,  trying vests, or different shaped jackets can take something that looks marginal by itself into a fashionable and flattering outfit. The more you can play this game with thrift store clothing, the more polished your look will become. (Without bleeding your savings dry.) 

Plus, finding great things for a bargain is fun!  And it’s even more fun if you experiment with a friend.  You’ll have a really good day together, laughing a lot.

Get an over 50 fashion mentor.

If you weren’t the type of person who was ever into fashion, then it can be easy to feel like it’s too much to try. This was my stance for years. After all, why was it so difficult to dress myself? That shouldn’t be hard, right? 

For me, finding a fashion mentor was key. 

I joined the Apple Shapes Collective on Facebook and started following Patricia Neely-Dorsey. I loved the looks she posted, and started trying some of the strategies she shared. 

Cathy loves Patricia, her fashion mentor,
Cathy follows Patricia’s fashion advice

As I asked about her various looks in the comments, she gifted me new vocabulary: waterfall jacket, trumpet skirt, swing coat, shift dress. It had never occurred to me that there were terms for differently-shaped pieces of clothing.

I started reading all of her posts, learning as I went. I bought new clothes, trying to mimic what she did with colour and pattern. When I posted a few photos and tagged her in my posts, she friended me. Not just in a Facebook way, but for real and started sharing advice and mentoring me. 

While there is only one incomparable Patricia, there are so many savvy and stylish people out there, sharing great advice in Facebook groups and other online platforms. Find a group for your lifestyle or body type, start engaging, and you are likely to wind up with some awesome fashion mentors! 

Cut the overwhelm with your signature fashion look.

Brighten up your denim shirt with an eye-catching red hat and a jaunty scarf

One of the stressful things about fashion is that it seems to change all the time. X is in and Y is out. Green is the new black. Blah, blah, blah. It feels like a club trying to keep us out. 

In and out is a game that teenagers play. You are over 50. You get to make your own rules and find out what makes you feel good. 

While you can get some great counsel on dressing for your current shape, how you take that advice and implement it is up to you–and it doesn’t have to be hard. 

The best advice I can give for waking up your dormant fashionista is to create 2-3 templates that will become your signature look. Here’s how to do that: 

Find your best shapes. 

The hit show What Not to Wear (UK and US versions) was game changing in putting out the idea that one size does not fit all. Consider that clothing comes in different shapes. For example in skirts alone there are mini, midi, maxi, trumpet, pencil, yoked, flirty hem, skater skirt, handkerchief hem, and prairie–and that’s not even all of them.

Take the basic clothing pieces: jacket, dress/skirt, pants/jeans and shirt and identify which shapes look best on you. If you feel really lost in this area, try something on, photograph it with your phone, and look at the picture. Does that shape work for you or not?

Being part of a group with fashion mentors can be really useful here because they can give you a heads up about what shapes work best for apples, pears, rectangles, etc.

Pick a colour palette. 

There many different colour theories when it comes to wardrobes. There are seasonal palettes like spring, summer, fall, and winter. There are minimalist color pallets where you chose 3 neutrals and a single pop of color. (Like black, white, tan, and red.) There are also programs like Dressing Your Truth, Color Me Beautiful, or Cladwell that help you find a palette that suits you. 

Choose a colour palette
Photo Sorapong Chaipanya on pexels

The most important thing to know is that identifying the colours that look best on you and limiting your wardrobe to this palette means every single thing you own will be working for you. (Wearing your best colours also makes you feel better in your clothes, too.) 

Then you’re ready to put together your new signature look!

Come up with 2-3 templates.

Once you have your colours and your shapes down, then it is easy to come up with 2-3 goto templates.   And that doesn’t just mean jeans/leggings/joggers to cover yourself up!

Over 50s fashion templates aren't just jeans and joggers
Don’t hide yourself in jeans and joggers
Photo by Ketut Subiyanto on pexels

For example, I’m an apple shape, so one template for me is: solid color waterfall jacket + solid tank + belt + printed skirt + boots. 

Another template is: lightweight printed jacket + solid tank + boot cut jeans + Chuck Taylors/Converse (you know, those lace up canvas basketball boots).

When you build your wardrobe around a few defined templates, not only is it easier to get dressed in the morning, but you also wind up with a wardrobe that “looks like you”.  Even if you never had one before, the result is a signature look that’s a long way from a frumpy stereotype.  

Over 50 Fashion is all about attitude

Lifestyle guru and actress, Marilu Henner, tells a great story in her “Total Health Makeover” book. Henner shares that she was with a friend once who was trying on coats. The friend became frustrated that none of them looked good on her, so Marilu picked some of them up to try them on. 

As Marilu modeled, her friend complained that Marilu looked good in all of them

Marilu turned to her friend and said, “It’s not the coat. It’s how you WORK the coat that matters.”

The way you stand in your clothes, the little accessories you use (that jaunty scarf) and the energy you put out as you are walking around in them makes all the difference in how something looks on you. 

So, go for the serendipity.  Ditch the clothes that make you feel frumpy and purchase those that give you confidence. Project an attitude and let your inner diva shine! 

After all, no one is going to know that you are making yourself look fabulous because you know how to “work the coat.”

Look at you, defying the stereotypes of over 50 fashion

How does it feel to walk around knowing that you look great? Has your confidence level sky-rocketed now that you have your very own signature look? 

Age means even less than sizes when it comes to fashion. And the next time a stranger stops you to compliment your outfit? Well, you can just smile knowingly and say “thank you.”  They don’t have to know you got it from a thrift store!

Be brave: ditch the frumpy and condemn the stereotypes. Over 50 fashion is as good as you want to make it. So go for that over 50 fashion fun.




Cathy Hutchison is an accidental over 50 fashionista thanks to some wonderful coaching. A writer and journal enthusiast, Cathy is the creative spark behind and teaches people how to journal with sketchnotes. 

3 thoughts on “Fun with Over 50 Fashion: 5 Timeless Tricks”

  1. Avatar for Joy Healey

    My sister is my ‘fashion mentor’. She’s the only one I trust to tell me if something looks good or not. Sadly I don’t live very close to her any more – and lockdown has restricted our visits. But it’s helped cut my spending too.
    Thanks for some great tips!
    Joy Healey – Blogging After Dark

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