September Style Guide: Dresses that Move with the Season

September is all about the shift—warm afternoons that still feel like summer, cooler evenings that hint at what’s ahead. The best pieces right now are transitional fall dresses: light enough to carry you through late-summer days, yet refined enough to ease into autumn. These three styles are designed to do just that.

The Hayden Dress in Black (gauze) 

Every wardrobe needs a versatile little black dress, and this one is made for the season’s in-between moments. Perfect as a summer mini dress with our Tkees Gemma Sandals or layers effortlessly with a cardigan or jacket and our Gold Hammered Hoops for fall. A timeless piece that proves easy style is always in season.

The Lizzie Dress in Brown Batik

Softly romantic yet grounded in earthy tones, this floral maxi dress is a perfect example of summer to fall style. The flowy silhouette feels effortless for coastal getaways or afternoons outdoors, while the print transitions seamlessly into autumn when paired with boots or a cropped sweater and our Pretty in Pearls earrings. 

The Haylee Dress in Pale Blue

Relaxed and elegant, the blue maxi is a go-to transitional dress. Its airy fabric works for sunny September days, while the muted hue feels right at home in early fall. Style it solo now, then add our classic Poseidon Coin Necklace and a wrap as the evenings cool down.

Effortless Summer to Fall Style

Transitional dresses are all about versatility—pieces that let you savor the last light of summer while stepping confidently into fall. Whether you’re searching for elevated Charleston boutique dresses or timeless silhouettes that carry you from day to night, these are the styles that make dressing with intention feel effortless from season to season.