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.

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!

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.

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!

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

So how are you transitioning? Share in the comments!