How to Dress for the Awkward Days Between Summer and Fall

The world is currently divided into two groups, especially when it comes to deciding what to wear during these late summer, early fall days. There’s the one group that claims fall is right around the corner, and the other that swears we’re still in the height of summer. I like to consider myself a realist, though, since I know that while temperatures are steadily cooling, fall officially starts on September 22. So before we can dive into the fall 2026 fashion trends, we have to make use of these awkward days between summer and fall, which, if you ask me, is when fashion is at its prime.

We’re in that comfortable gray area where a sweater won’t make you sweat, and a skirt won’t leave you freezing. There’s no heat wave, no icy gust of wind; just mild temperatures perfectly suited for every type of silhouette. I am currently in a short-sleeve cashmere polo, lightweight trousers, and heeled mules—a mix of summer silhouettes and winter materials that are made for these in-between seasons. The best looks come when you’re not constrained by tricky temperatures, so go ahead and wear those leather pants with linen tanks. Boots with miniskirts? Why not? Here are all the ways to dress for the awkward days between summer and fall.

Bermuda shorts with everything

My secret to always looking sleek, polished, and professional without breaking a sweat? Bermuda shorts. They pair with just about everything—blazers, tanks, sneakers, and flip-flops alike. They cover more than your average shorts but allow for plenty of airflow to keep you cool. During these awkward in-between days, I’d style them with a T-shirt and a cardigan, the latter of which I can always take off or tie over my shoulders when it gets hot. Once the temperatures drop even further, I’d opt for a tank and blazer instead.