How to Wear Summer Dresses & Shorts In the Fall

I’ve been living in maxi dresses and tank tops all summer, but before we all know it we’lll be replacing those pieces with bulky knits. I’m making the most of my lightweight apparel by transitioning them for colder weather.

Here’s how to accomplish the summer to fall style transition without sacrificing comfort on brisk mornings and chilly evenings. Yes…you can wear shorts in the fall!


Transition: Dresses


Your summer dresses (featured: June & Hudson animal print midi dress, $68) won’t feel quite so comfortable when it’s down to sixty degrees on a dark fall evening. The solution: Layer them over a pair of warm leggings, like these by Hue ($36, sizes XS to XXL).




Top it off with a jacket that’s not quite winter-ready, but just warm enough to keep you comfortable when winds pick up. This Caslon Hooded Drape Front Knit Jacket ($59) is a great choice.

Transition: Bright Colors



During summer, you wear vibrant floral prints and engaging rainbow hues like it’s your job. But come fall, there’s this odd tendency to shove it all to the back of the closet and slip into somber, drab colors that make you look like you’re perpetually in mourning. I’m addicted to my silky, floral, hot pink tank (I know, what a girl!), but I’m not letting go of it just because it’s about to cool down. Instead, I’ll layer it beneath a black sweater, like this Nic + Zoe ($98) that can be worn in four ways, and let it be the focal point of my look. A pop of color makes all the difference during fall!


What about that lightweight scarf you wore in your hair while you strolled the boardwalk? It works in much the same way as a colorful top. Slip it around your neck and pair it with something extra neutral, like a pair of jeans, a white tee, and a cardigan, like this from MNG by Mango ($34.99), for maximum impact.

Transition: Shorts


There’s only one real way to pull off shorts in the fall, and it’s not the most practical in the world. Yet for some, the temptation is enough to give in. If you’re a slave to your favorite shorts, slip them on over a pair of tights and throw on a military-inspired jacket, like this one by Lucky Brand ($38.49), to keep the look casual.


A pair of booties offers a flattering way to finish off this choice look. Steer clear of too-high heels and stick with a low-profile style, like these Crown Vintage Larin Western Booties ($79.95). These wear well all season long, with everything from jeans to dresses, so consider them a chic investment.

More Fall Fashion: