We would not be exaggerating if we said that skirts were among the most important staples of a ’90s minimalist wardrobe—especially the flowy variety that allowed plenty of movement. Back when stylists didn’t dress celebrities in formulaic fashion choices, they would style themselves in carefree, effortless ways, which would go on to become trends. Think: Jennifer Aniston, Gwen Stefani, Salma Hayek and Meg Ryan, who became the poster girls of ’90s style. And they all had one thing in common: they all wore skirts. Yes, even on the red carpet.
As we continue to look at fashion with a sepia lens of the ’90s, there’s no better time than now to revert to flowy skirts from the era that are headed for a revival this fall. And while sneakers and ballet flats will always be great footwear options to pair with skirts, this season, we are looking toward ankle boots to add the perfect finishing touch to your look. Your pleated, side-slit, and sometimes flared designs will find their match in a pair of heeled, pointed-toe, or even slouchy ankle boots. Here’s how we are styling ’90s skirts with ankle boots in September 2026.
Flowy skirt + suede ankle boots
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