Clothing In from Summer to Autumn—How to Transition

There’s something about the end of summer that makes me somewhat sad but at the same time, I welcome the arrival of crisp, cool weather.   Actually, it’s a few “somethings”.  The days get shorter. This is a double-edged sword simply because I despise driving in the dark.  Yet, I find that the shorter days help me to be more structured with my time management. It’s weird.

a pile of autumn leaves

Autumn is definitely my double-edged sword. While not quite ready to say goodbye to summer on one hand, on the other hand I’m mentally ready for Autumn!

The days of running out of the house in one of three ways; holding sandals in my hand, wearing sandals or just getting into the car and driving barefoot (as well as practically living barefoot). These days are replaced with having to wear shoes. Again—it’s weird simply because I love shoes but equally adore naked feet.

My number one choice of footwear during summer is…nothing! But I can’t go barefoot all the time so the sandals are worn until the first frost–with rainy weather being the exception.  Then when it’s too cold for sandals the shoes come out! I march into Fall accordingly!

I don’t have to adorn myself in outerwear during the summer. In fall it begins with a short-sleeved tee shirt compared to a sleeveless top. Then comes the blazer or denim jacket—those are all fine. But as the balmy atmosphere turns into the damp, gray, chill of late autumn into winter, I cringe at the thought of having to put a heavier coat on—and stuffing a heavy scarf into the coat.  It’s about how many pairs of gloves will become either lost or mismatched and I simply cannot stand cold hands on a colder steering wheel. On the other hand, I do prefer wearing gloves that match!

22 Best Winter Coats for 2021 - Elegant Long Winter Jackets for Women

Outerwear isn’t my priority. I’m good with one coat and the coat I have is similar to the one in the middle. I can’t even drive my car wearing a coat because it’s too cumbersome. Do you feel the way I do?  And..the coat doesn’t even make an appearance until November!

My wigs keep my head warm. They are a sort of hat. But when the wind kicks in and sends my fake hair falling into my eyes, my nose and my mouth, a hat keeps those wind-blown fibers at bay.

Ugh. I can’t believe I actually have a filtered photo. Anyway, my hat of choice is the beret. This wool cute was less than 5 Euros in Paris. I suppose I should start looking for it now because by the time I find it, the first snow will have fallen!

I may be getting ahead of myself with the weather talk because autumn seems to arrive later and later each year. I can remember wearing shorts at the beginning through middle of October in past years and wearing but a sweater to take the kids out on Halloween.

And yet, pumpkin spice everything and..

…these offensive fake cinnamon-scented pinecones make an appearance earlier and earlier.  WTF buys these stinky things anyway?

However, the days have been cooling off rather quickly this September. And even though the temperature reaches a crescendo of up to 90 degrees mid-day, it cools down by the time everyone is leaving work or getting dinner ready.

It’s that transitional time of the year.

And what to wear can often be a challenge.  The air conditioning system at the office, or at the supermarket or restaurant will still be running—making the indoor air that was comfortable during the heat of the summer, ever-so-chilly during this time.

Those sundresses of last month aren’t exactly behaving in a seasonal manner after Labor Day.  The tan is fading and the arms and legs, unless you break out the fake tan, are looking a bit pale against those bright colors we were loving in June, July and August.

But it’s still too warm to break out the wool skirts and pants and cashmere sweaters. Not quite boot weather yet either. So, what to do? How to dress? My advice?  Take baby steps. Transition slowly—not at once. It isn’t time yet. October can get brutally balmy.  I usually bring out the heavy gear in November and wear them well into April.

No. No. Nooooo…we are NOT bringing out the wool blazers and heavy denim shirts yet…I’ll show you how to gradually do it!

Let’s have a look and I’ll show you how I’m doing it.

Take a pair of pants.  I’m wearing the Jamie Pant from J. Crew Factory. Wear a loose white tee shirt.  Add a pair of sandals (these are from Rondini). You have a great ensemble for the end-of-summer–cool in the AM and PM and hot in the day.

Uh oh! It got a bit chilly outside. Replace the tee with a denim shirt (also from J. Crew) and perhaps a different pair of sandals (Tory Burch Miller sandals)

Ohhhhhh. It’s an unseasonably cold day in October–and November is just around the corner. Add a wool-blend blazer (also J. Crew) and to dress things up a bit, a pair of pointy-toed heels! I’m even transitioning to darker hair in the form of Hudson by Estetica!

Pants. Back in the Spring, I purchased two pair of paper-bag waisted pants at Target. I did wear them during the Spring, and stopped during the June/July/August months. I just cannot stand to wear pants when the weather is hot. They are uncomfortable, and when my body gets really hot, they are cumbersome.  These pants, though, are loose, lightweight and fall just above the ankle, making them comfortable for both the cold to hot weather and the hot to cooler weather.

These paper-bag waisted pants are a wonderful item to transition into Autumn. Light enough to wear on the warmer days with sandals and a form-fitting tee. As the cooler weather appears, replace the sandals with a ballet flat or loafer and a cropped sweater to replace the tee!

More loose pants, although not paper-bag waisted, are another option because of the loose wider leg and the elasticized waist. The looser leg, as well as the lighter fabric, make these pants perfect for transitioning.

The J. Crew Jamie Pant is also a wonderful transitional option. At this point flip flops or sandals can be worn, but the leopard print and dark shirt scream “Autumn”.  When it gets too chilly replace the flip flops with a cute bootie, boots or heels. 

Leggings will also have their place as the weather cools off. A tee shirt and denim jacket will work wonderfully, and to be so inclined, if I want to dress it up a bit, I can through a blazer over the tee.

Leggings. These were worn last week. It was rainy and damp and gray. Although too wet for sandals, ballet flats were the choice. But as rainy and damp as it was, it was still very warm and muggy. A sleeveless shirt worked well.

And the great thing about leggings is that the current ones are not the flimsy leggings of yesteryear. Leggings can be pants.

Transitioning the legging ensemble. First pic. The white tee, leggings and sandals are perfect for now.  In a few weeks it’ll become a bit cooler so lets change into heels and add a blazer–a great work look. Wait! Let’s get a bit edgier, shall we?  Take the heels off and switch into a pair of Nike leather sneakers. A look that works for the weekend when you don’t want jeans!

My Wynne Maxi dresses from Lilly Pulitzer are the greatest transitional dresses ever.  A maxi dress isn’t my thing during the winter. And during the summer, these three dresses were worn a lot! But they are also the perfect transition dress. The length will be fine through the early fall. And with a denim jacket –will be remarkably autumn friendly. I will add one caveat. I never wear closed shoes with a maxi. Only sandals will do it for me. So as soon as the first chill arrives, I’ll store the maxi dresses away.

Ahhh. the Wynne maxi dress by Lilly Pulitzer..

Two of the three I own, these have been worn from lat Spring into early Fall, truly a three-season frock. Although I only wear sandals with maxi dresses, that’s just my thing.  But when the cooler weather arrives, I’ll wear both with a denim jacket.  Proof that you don’t need a separate wardrobe for every season!

The most basic and most simple way to transition for the season. Add a denim jacket!

The summer shifts.  There are a couple of shift dresses that I’ll keep into fall.  One is my absolute favorite. It’s a Tyler Boe dress that was purchased at a sidewalk end-of-summer sale a few years back. The dress retailed for over $100 and I picked it up for around ten bucks.  The high neckline was made for the cooler days and, once again, with a denim jacket, it will be very autumn friendly. Sandals or ballet flats will complete the look.


On it’s third summer-into-fall, this Tyler Boe dress was a steal and I’ve worn it countless times. Bonus–you don’t even need to wear a bra underneath–that’s an epic summer dress. But as the days get cooler, this denim jacket from Kut from the Kloth is going on five or six years now.  It’s another favorite transitional look!

This gauze dress from J. Crew Factory, also purchased a few years back is another great summer-into-fall item. The gauze fabric is light enough for summer yet will be fine for early fall.  This is one of those casual dresses that also looks great with Converse sneakers.

I wore this to work today. The temperature hit 90 so it was a great choice. Bonus! The loose cut is very weight–gain friendly. When I bought it I was 20 pounds lighter and it still fits..

The day I bought this transition-friendly cutie–she looks great with converse sneakers. Damn. I got so heavy!

Here’s another way to transition a summer dress!

Remember–it’s still summer and this sleeveless dress isn’t going anywhere but on my body–and the sandals are still hot-weather appropriate..

It got a bit chilly out . Throw a blazer over the dress when the weather cools off–besides with heels, it’s a great work look..

Or don a denim jacket for a fun vibe!

The sandals, by mid-October, will be put away for next spring and the ballet flats and other shoes, will be taking their place.

The best way to transition is to take baby steps!  Slowly change up the footwear!

A white tee shirt is essential for transitioning.  Honestly, every wardrobe needs at least a dozen.  

Two more essentials.  The blazer. Navy, black and camel are all you really need. And the denim jacket. This one is by GH Bass. I have  this dark one and a lighter blue.

Heavier sweaters will make an appearance later in the fall. As will the boots.  I don’t want to get too far ahead of myself seasonally because it’s still summer for another two weeks. And it’s not cold yet.

Bundle Up A Christmas Story GIF by filmeditor

Please don’t bundle up like this in September–or October. Let’s do this gradually!

Besides, I cringe when I see people wearing the winter garb in early fall. It gives me hot flashes and makes me sweat so much that I need to add a stick of deodorant to my purse!

samantha jackson GIF

This is me when I see people dressed in winter clothing in September!

So how are you transitioning? Share in the comments!

About Catherine

Far from perfect, but enjoying life as a non-perfect and flawed individual at 60 years young. I'm still wondering what I'll be when I grow up! The characters in my life's screenplay include my better half. He is a refined Frenchman who grew up in Paris and summered in St. Tropez. I grew up in Long Island and summered in Long Island. I am not refined. My three grown children are also a big part of my life. For their sake, they happily live where their careers have taken them! But I can still mother them from a distance! I write about the mundane. I write about deeply shallow issues. But whatever I write or muse about--it'll always be a bit on the humorous and positive side! It's all good!
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11 Responses to Clothing In from Summer to Autumn—How to Transition

  1. Bonnie says:

    It is a bit tricky to know what to wear when one day it is warm and the next cool or cold. You laid out a good plan using summer clothes and laying. I love fall and winter clothes. Happy to give up white pants. Bring it on.

    • Catherine says:

      Hi Bonnie. Yup! It is such a challenge deciding the clothing game during this time of year. Pants are just still too cumbersome for me unless they are loose I[m, pretty-much sticking to dresses with slight layering. But…I am looking forward to that first chilly day! XOXOXOXO

  2. Momcat says:

    Some great ideas! Denim jackets are the best for transitioning into Fall! Also little cotton neck kerchiefs with a light t shirt and denim jacket look cute if the neck gets cold but not wanting a heavy scarf. I think I have one more pedicure left in me so I can continue with sandals for another month. But who knows? It’s Canada and I might be in a parka and snow boots!

    • Catherine says:

      Al, the pedicure! I swear I was just thinking about how many pedis I have left before stopping for the cold weather when nobody sees my feet. Because I transition into shoes so late in the game, I probably have three left! Perhaps two depending on the weather. I like a lightweight scarf to hide the turkey neck! And now, I have a cold neck just from the mere thought! But the denim jacket is such a great addition to a wardrobe. Those jackets always look great and are a more casual option than a blazer! LOL!!! XOXOXOXO

  3. di says:

    Thanks for the trasition looks. what you put together for us looks so easy and stylish, but it took some thought and time in the background, because it does not look thrown together. Thanks for the tips on early fall looks. Here is a tip for you !

    Here is my tip … I wish you would
    include the names of ALL the wigs you wear in your different blogs, you change them up, and coordinate them so nicely with your wardrobe style. I may be able to recognize a Lilly Pulizer dress, but I cannot identify the wigs by name,. I thank you for being frank and honest about wearing wigs and they are a big part of your style and you seem proud of your ever changing looks. My face proportions are the same as yours, so I would like to see the wig names,,,as I finally have found a super Delightful face to model the wig for me.
    Thanks for what you do.

    • Catherine says:

      Di. Your suggestion is wonderful and I thank you. As of this day, moving forward, every wig will get a mention! I might not remember the exact color but I’ll definitely name that wig and who it is by. Thank you!!!!!!!!!!!!!! XOXOXOXO

  4. Maryellen says:

    Repling to Momcat’s comment….what is it with cold necks as an older person? My neck never used to be cold when I was young. I too use the small neck scarves to jazz things up, transition to Fall, but also to keep my old neck warm!

  5. Marsha Banks says:

    Love the ways took each basic outfit and then fall-ized it! I used to do the same with shoes/sandals, wearing sandals until snow actually fell. But, then my thyroid went haywire, and my feet freeze. So, I end up wearing closed shoes earlier than I used to do.

    • Catherine says:

      Hi Marsha! Oh..the shoes. I wore sandals today while everyone at the office was in actual shoes. The A/C was on and when I left the office to go home, I made sure the AC was shut off! Hey. If you don’t mind my asking, how did you know you had thyroid issues. I”ve had my thyroid tested a hundred times and it still comes up within normall range! XOXOXOXO

  6. Juliet says:

    Love the very gradual transition – that is so clever!!!! I dont even want to imagine my wardrobe without my trusty white tee shirts – no matter what the weather, they are a staple of my wardrobe, having moved within the last 6 months from Scotland to England I’m curious to see if there will be a slight difference in our climate – hopefully no more black ice which was horrendous, any other weather I can cope with, but skittering about like a little penguin is just miserable. Winter weather means woolly knits and as a knitter I am delirious with joy at the possibilities, I have a magenta coat – sadly beige makes me look horrendous so I can only admire that chicness on other people, however a bright coat makes the navy/grey/black/white items really pop and cheers me up. I love Kim Cattrall she made SATC so funny, such a fabulous talent.

    • Catherine says:

      Hi Juliet! Ohhhhhhhh I would be so lost without my white tee shirts. They are the best essential and perfect for layering. Don’t mention black ice. It’s so dangerous and can be so very tricky. One of my friends broke her wrist in March falling on black ice. I’m so jealous of you that you can knit. My ex-MIL tried to teach me to knit but I couldn’t get the hang of it-LOL!! Kim. Was. Greatness! XOXOXOXO

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