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Fall Fashion After 50: 4 Transitioning Clothing Ideas for Autumn

By Jodie Filogomo September 21, 2023 Beauty

It happens every year. The chill starts coming in more noticeably in the mornings and evenings, and we start thinking about the autumn season that is approaching. Depending on where you live and how you spend your day, it can be easy or challenging to figure out what to wear during this transition to autumn!

Let’s review a couple of fun ways to make choosing an outfit during this temperature change work yet still look modern!


Layering has to be the most obvious choice for fall transition! Putting another piece over your tank top, lightweight shirt or other lightweight item creates the perfect opportunity to also remove them if the temperatures heat up!

It may also seem silly to have on a layering piece with bare legs if you’re wearing skirts or capris, but that’s exactly how you can stay comfortable during these changing temperatures.

Many of these layering pieces you may already have in your closets. But it’s also fun to check out some of the newer offerings in the stores, to make sure your look is updated. I’ve addressed the fact before, that looking contemporary is the best way to appear knowledgeable and relevant!

Cardigans and Jackets

I know that the lightweight cardigan sweaters are something we all probably own. During this period, the ones I tend to reach for the most are the ¾-length sleeved ones! If you wanted to get an update to this item, then I’d look for the longer cardigans that extend to the mid-thigh or below. Either that, or pull out the kimono! These are lightweight but offer just enough coverage!

Button-Up Blouses

Another piece that you don’t always think about layering is your button-up blouses. The chambray shirts are perfect for this, but even your lightweight blouses can be a great “jacket” when you don’t need something heavy.

This would include a sheer blouse that you might own which is usually worn over a camisole or another top when buttoned. Worn this way sheer blouses can be as wonderful as a jacket.

The other layering pieces that seem to be popular right now are vests. I’ve been seeing a ton of utility and denim vests. They can add just the right amount of warmth, yet not get you too hot since they don’t cover your arms.

Then, of course, there is the classic denim jacket. This is probably the easiest piece to add over any outfit! Denim is having a blast in the style scene, since it goes with absolutely everything. If you don’t already have one of these in your closet, you might even check out the thrift store! They look great even over a dress!


The other obvious choice to chase away the chill is your shoes. Of course, you can always wear your closed toe shoes, but the most modern footwear right now are the ankle boots.

There were many of you who are under the impression that ankle boots don’t look good with most outfits because they can break up the line of your leg. That point may be true, but our eye gets used to a certain look or style. Wearing your ankle boots with skirts and dresses is fun!

This is also the time when those open toed booties you thought were silly can actually seem smart. These booties cover your foot enough to keep it warm, yet there is enough ventilation that your feet aren’t sweating profusely! Even if you don’t like the open toed variety of the ankle boots, there are also versions that feature cut outs and perforations!


Adding a scarf around your neck is just another version of layering! If you’ve ever embraced the versatility of scarves, then you know how perfect they can be during these seasonal transitions!

Your scarf is not much different than a topper in that you can remove it if the weather becomes too warm. If you’re wondering about where to put it when you take it off, how about tying it on the handle of your purse? It can still be decorative there, yet won’t heat you up!

It’s amazing how this little piece of fabric can add just enough warmth when you need it! I think the smaller neck scarves are the perfect way to not only keep away the chill, but to also add some fabulous color to your face! Or you can take a square scarf and fold it and roll it to create a neck scarf! I have a bunch of YouTube videos on scarf tying if you are interested!


Another interesting way to work your way through the seasonal transitions is to start adding in the darker colors to your outfits. This could mean that you wear an all-black outfit with a pop of color. Or you could take your favorite summer skirt and pair it with a darker or more muted color.

Certain colors tend to remind us of autumn. For example, your dark oranges, burgundies and olive greens. So why not pair these “fall” colors with a color that you usually reserve for the spring and summer, like pink? It’s a perfect way to have your outfits work for these fluctuating times between seasons!

Let’s Have a Conversation:

What are your favorite fall clothing styles or outfits? So what are your favorite ways to transition your clothing through the cooler weather? Please share some ideas in the comments below!

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Sorry, those outfits are awful. Not appealing at all on these women. I’m way older than fifty and I don’t even dress like that. I might be different but I know how to put myself together not to look older or a young teenager. Just because you’re getting older doesn’t mean you have to dress frumpy. There are lots of older women out there that look very fashionable not frumpy looking. My, my, my.


Oh my word, these are very frumpy and dated clothes and some outfits are very unflattering with clashing colours/patterns and not suited to the women’s body shapes… Even if buying secondhand, I am sure most women can do better than this.

Last edited 6 months ago by Ingrid

Denim Jacket, Sweaters, Cords and scarves definitely. Ponti knit pants, pretty blouse, Ponchos as well.
Being comfortable is more important than being in high fashion or designer clothes at this stage of my life. I’ve been pinched enough in my life. Not comfortable? It goes back on the rack or sent back.
Some of the outfits are better than others in the above photos.
I like Denim & Co, Coldwater Creek, etc…

I’m new to this site. I will be 82 years old next week. I live out in the country near the California coast, don’t drive and don’t go much of anywhere. I have no reason to even wear a skirt.I enjoyed these fashion ideas. I’m dressing for the occasional casual event. I don’t need to be going out for tea or grand parties. I’m dressing smartly, casually, and am even thinking of bringing out my old boyfriends’ Levi jacket after seeing these fashion styles.

The Author

Jodie Filogomo is a retired cosmetic dentist turned style consultant. After over 20 years as a successful dental practitioner, she enhanced her styling talents by taking fashion, interior decorating and design classes. Jodie loves to share with others her passion for putting together outfits for women of all ages. Visit her blog Jodie’s Touch of Style and connect with her on social media.

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