Casual Transitional Dressing for Fall

Casual Attire

About this time every summer, many of us find ourselves longing for the gloriousness of fall fabrics and styles; however, the heat of summer prevents us from truly dressing for cooler weather.

I happen to be one of those people looking to enjoy the ambiance of fall clothing without the weight of it—so I set out to find some fabulous casual transitional pieces that will fit the bill. The looks I found are “all fall,” but the lighter-weight fabrications will help keep you cool as summer continues to press on.

That said, let’s dive in. I mostly stayed with earth-tone neutrals as they, at least for me, represent the feel of the fall season. You’ll see that I found some delicious tops, bottoms, some dresses, and even a fun jumpsuit to get things started. And to complete your look, I’ve even shopped third pieces and some adorable shoes! In short, I found a host of useful transitional treasures!



Let’s start our fall transition looks with tops. You will never go wrong with an iconic white T-shirt regardless of the season. This wardrobe essential will always “pop” your look, so naturally, I included a few of them. I particularly love the idea of the off-white choices you’ll see. When they are combined with the pants and jeans I’ve shopped, they create that fall vibe we are seeking.

The dresses I’ve included range from chic sophistication to just plain fun. Wear a pair of delicate strappy sandals with the dressier styles and anything from flip-flops, slides, or sneakers with the more casual options for fabulous fall transition looks.

Each of the tops and dresses I’ve included in this post is a winner and will serve you well for years to come.


Each of the pieces you see in this section is phenomenal! They are foundational in building your transitional fall look, and many of these gems will serve you year-round.

Be sure to take a close look at the jeans as denim is a staple we cannot live without, and you are going to love what you see. The pants range from dressier wide-leg menswear type looks (in cotton and linen) to more casual options in olives, khakis, and other yummy earth tones. And the skirt—well, it is just plain fabulous!

All that you see in this section will work beautifully to create the transitional look we’re going for, and yet much of it also falls into the “I can wear this all year” category as well. What could be better than that? Trust me, you’re going. to want to snap up these pieces!


When it comes to the third piece that you’ll choose to complete your look, you want nothing short of a show-stopper. Your third piece should have that “wow” factor we should all aspire to every time we get dressed.

I’ve found some stunning pieces for you—from an incredible lightweight cream-colored double-breasted blazer (which will be perfect over a white T-shirt) to Shackets (shirt jackets), tiered jackets, cardigans, and everything in between. Any of the pieces in this section will get you an incredible bang for your look. Your biggest problem will be deciding how many of these wardrobe must-haves will make their way into your closet!


In this post, I’m going to focus on fun, fabulous shoe finds that you can wear now—as well as all next spring and summer. They will work beautifully in creating the transitional fall look we’re going for, especially paired with the delicious pieces shown above.

I have intentionally passed on boots this time because, depending on where you live, you’ll be looking to wear them in another month or so. At that time, we’ll make sure you have plenty of them from which to choose.

In the meantime, the shoes I’ve shopped for you will take you to fall and beyond. You can wear the flip-flops on those mild, golden Indian Summer days, and even the slides can be worn in the colder weather. Anyone who knows me knows that I love pairing chunky socks with slides. I’ll wear them on non-rainy/snowy days all winter long!

And who doesn’t live in their sneakers? They are always a welcome addition to anyone’s wardrobe. The high tops I’ve found add an element of edginess to your look, the clogs are perfect worn with your wide, bootcut, and flare-leg jeans, and the driving moccasins are both timeless and seasonless too.

So, with so many amazing shoe options, which will you take home?

We all know from personal experience how challenging transitional dressing can be…

So here’s to a much easier and chicer experience transitioning seasons this year! 

PSSST! Looking for more curated shopping? Check out some of our other recent posts!

Utility Pants and Jackets for Timeless Casual Looks
Beat the Heat: Fabulous Summer Finds!
Style 101: Essential Styling Tips

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