What to Wear in Late Summer: Transitional Outfit Ideas for Breezy Days

There’s a certain moment when summer starts to shift. The sun still lingers, but the air feels lighter. It’s that in-between season where you're asking yourself: what do I wear when it’s still summer—but kind of breezy?

You’re caught between not wanting to overheat and not wanting to freeze. This is the season of second-guessing—when your go-to summer staples suddenly feel too bare. What you need now are pieces that move with the weather: light enough to breathe, but with just the right amount of cover.

Here are four ways to dress for the in-between: polished, breathable, and ready for the forecast to change:

1.Linen Layers

Matching linen sets strike the balance between ease and intention. They’re breathable, polished, and always feel pulled together without the effort. A uniform you don’t have to think twice about.

Get the Look: Hanson Shirt and Masha Shorts & Nola Top and Elysia Pants

2. The Swimsuit-and-Pants Look

When the days stay warm but the air shifts, a swimsuit paired with pants is the perfect seasonal bridge. It’s effortless, versatile, and made for that not-quite-fall mood.

Get the Look: Lyra Swimsuit & Helena Pants

3.A Hint of Asymmetric

An asymmetric dress brings just the right amount of edge to transitional dressing. Its off-balance lines feel effortless yet intentional—light for warm days, and layered enough for cooler shifts.

Get the Look: Coraline Dress & Sarita Bikini

4. The T-Shirt Dress, Seasonless

Minimal, unfussy, and endlessly wearable. The T-Shirt Dress shifts easily between settings, offering just enough structure without ever feeling overdone. In transitional weather, it’s the piece you reach for without hesitation.

Get the Look: Lavinia T-Shirt Dress

Transitional dressing doesn’t need to mean heavy layers or a full wardrobe refresh. With a few versatile pieces—like linen sets, asymmetric dresses, and t-shirt styles—you can move through late summer in comfort and style. From easy-to-layer silhouettes to swimwear paired with tailored pants, these transitional outfits make effortless dressing feel seasonally right.