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October 23, 2026
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The Summer-to-Fall Dresses You’ll Keep Wearing Into September

The end of summer doesn’t mean the end of fun clothing, like packing away all your dresses. The secret to getting more wear out of the category as the weather cools, is choosing pieces with high coverage (long sleeves, midi and maxi hems) and heavier fabrics for warmth. 

We’re preparing our back-to-school wardrobes with some of our top favorite brands, including Free People, Madewell, Aritzia, and Anthropologie have seriously good markdowns on dresses that feel especially right for this September. 

For keeping comfy but cozy in the seasons ahead, think of dresses like sweater-knit minis, polished shirtdresses suited for the boardroom, or denim midi dresses that can go anywhere. These on-sale picks are all versatile enough to keep in rotation well into the holiday party season.  

No matter the style aesthetic you’re choosing for fall, be it bohemian vibes or corporate-core, there’s a little something for every fall mood, now on sale.

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