Endless Summer: Transition Your Style from Summer to Fall

Catherine Cassidy (Business Heroine Magazine)

I’m my personal styling business, I’m all about maximizing your wardrobe. One of the best things about being in Southern California is that you don’t need to necessarily transition OUT of your summer clothes. You just layer over them for warmth when you need it. The only things you really store are your sweaters and boots … and even still you may wear them on a cool summer night.

Well, in DC there really aren’t any cool summer nights. Even if we’ve enjoyed a relatively mild summer this year.

It’s also quite different transitioning when you do have REAL seasons to take into consideration.

Either way, I love to prolong the wear of our favorite summer styles into fall with just a few easy tweaks …


For me, personally, I LOVE white! It creates such a clean look. A white blouse or tee is a key element of MY style and I do believe every woman needs at least one.

In summer, you’ll often find me in my white jeans. In LA, that was my staple. Here in DC, it’s an evening staple more than a daytime one with this heat.

But, women always want to know: Can I wear white after Labor Day?

And my answer is absolutely YES!

The reason why that rule came about had to do with the changing weather and keeping your white CLEAN. So, as long as the weather is still nice, wear your white! (I’ll even take this further and into the winter when the weather is clear … yes, such a rebel!)

Take it from Summer into Fall by:

– Wearing boots instead of sandals

– Layering your cozy wrap cardigan over your blouse

– Add a blazer to the look for chic business casual


What I love about a good maxi dress is that it makes it SO easy to be comfortable, but also dressed up and polished.

The key here is quality. Because many maxi dresses tend to be knit, you don’t want to skimp too much on price or quality. Otherwise, you’ll end up with a dress you LOVE but is already wearing out because you wore it so many times this summer (think faded + pilled).

Also, fit is important. It’s really easy for a maxi dress to also maximize you. Make sure you see your waist somehow. Ideally it’s because the style comes in AT the waist, but it can also skim. If it needs more shape, add a wide belt at the waist.

(Why a wide belt? Because usually there is a lot of fabric with a maxi dress, so you need to create more definition than a slim accent belt will create.)

If there isn’t much shape, this is when the FALL elements will actually help you create better shape and style with your beloved maxi dress.

Take it from Summer into Fall by:

– Adding a cropped moto jacket (also defines your waist)

– Layering a belted cardigan over the dress paired with boots

– Add a jacket!

– You’ll want to wear your boots, not flats, instead of sandals


There is always so much COLOR in stores in summer, which I love! The stores always turn more somber and dark come fall … which is why I still like to revert to my summer staples even in the fall to add some FUN to my style.

In fact, I wear them year round when I can.

Again, in a city with true seasons, you may not be able to get away with this … but some of these summer into fall tips for your summer tanks can even last you through winter!

Take it from Summer into Fall by:

– Untucked over your pencil skirt but belted with a jacket over it (add tights in winter)

– Tucked into your favorite pencil skirt with boots and a cropped cardigan

– Layered under your basic blazer (or favorite leather jacket!)

– Adding a pop of color under your dark cozy cardigan


maximizing wardrobe - catherine cassidy

Business Heroine Magazine


We’d love to hear from YOU…

What is your favorite item to transition your style summer to fall? What are your favorite fall staples? Do you live in an area with true seasons, or can you get away with layering your summer clothes year-round? Leave your answer in the comments below! 





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