What to Wear 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.

Boots with skirts, dresses, and shorts

Moto boots have emerged as the summer It shoe. While you don’t need to jump on every single trend (who has the wallet for that?), you can slip into any style of boots you own, be it combat boots or heeled boots, and style them with short-hemmed bottoms. Use these milder temperatures as a chance to match leather with summery ensembles.

Long-sleeve dresses with thong sandals

I reserve all my long-sleeve and knit dresses for the weeks leading up to September. While fall might call for sneakers or boots, the end of summer allows me to wear my favorite strappy sandals instead. And while the sun is still out, I’d grab a trusty pair of sunglasses to finish the look.

Mixing silhouettes

Lace-trimmed shorts continue to trend into early fall. Instead of wearing them with a breezy tank, opt for a fall-forward silhouette on the top. Long-sleeve white T-shirts are the latest addition to the capsule wardrobe and pair impeccably with lace-trimmed shorts. Instead of open-toed shoes, a pair of ballet flats or loafers feels more fall-friendly.

Blazers and ballerinas

You know autumn is around the corner when the blazers come out. Consider the next few weeks to be your opportunity to wear them with skirts, shorts, and dresses alike. While I typically style blazers with sneakers or heels, I’ve recently been into pairing them with flat shoes like ballerinas. The feminine silhouette balances the more structured figure of a blazer, creating a visual balance that scratches the brain just right.

Summer silhouettes in winter textures

Take all your favorite summer silhouettes—think skirts and tanks—and find them in winter textures. This show-goer was spotted in a croc-embossed leather skirt styled with a lightweight long-sleeve top. You can also try a short-sleeve top made of cashmere or a minidress made of wool. These styles can typically only be worn during that small window between summer and fall, so make sure to grab this fleeting opportunity.

Winter silhouettes in summer textures

The same can be done the other way around. Take your favorite winter silhouettes, such as pants and long-sleeved tops, and find them in summery textures. Silk, linen, and cotton poplin are great temperature-regulating materials to opt for during this time. They allow you to dress modestly without working up a sweat.

Socks with sandals

Should you feel bold enough to try the controversial socks-with-sandals trend, now is the time to do so. Summer and fall collide in this footwear style as it becomes too cold for open-toed shoes yet too warm for closed-toe boots. The combo is surprisingly easy to pull off when paired with a short-hemmed bottom like shorts and skirts. This is certainly an easy (and comfortable) way to add an editorial touch to any look.

Track jackets and shorts

Windbreakers and track jackets were just picking up momentum when the heat wave came crashing in, leaving them dormant for a season. As the more soothing temperatures roll back in, we’re picking things up right where we left them and bringing the trendy silhouette back to the top of your mind. You can pair them with the aforementioned Bermuda shorts, or swap in balloon pants once we get deeper into fall.

Easy layering

’Tis the season of layering, meaning it’s time to wrap your jacket over your cardigan over your T-shirt over your tank. If you want to take it a few steps further, layer long socks under your loafers. The goal is to have multiple items you can take off should the temperature change its mind midday. Fall weather is notoriously finicky, and you never know whether you’ll be freezing or fuming, or both, so let’s stay prepared.