Nili Lotan Jacket, Me + Em Cardigan, Rohe Skirt, Aquazzura Boots, Alaia Bag (sold out, similar here); Girl’s Faux Fur Coat

Skirts are the quintessential alternative to pants this time of year, an easy way to dress for gatherings and early festivities. They slip easily under a sweater or pair neatly with a blouse or turtleneck, fitting naturally beneath this season’s jackets and coats. Styled with tall boots, loafers, or heeled mules, a well-cut skirt brings shape and distinction to autumn dressing. From pleated and fringed to leather, suede, animal print, and embellished designs, each finds a line of its own this season.

Taylor Swift really does have that good girl faith and a tight little skirt.

Through the years, Swift has blessed Us with a number of fabulous skirt moments, from leather numbers to denim skorts and more. In March 2024, she looked seriously stylish in a pleated tan $695 skort from Sandy Liang while enjoying a Malibu lunch date with boyfriend Travis Kelce.

Swift rocked another fabulous skirt in October 2023 while on another date with Kelce. For the duo’s New York City outing, she wore a $2,100 leather Khaite Keene Leather Mini Skirt backwards and a sheer Jean Paul Gaultier top.

One of her most coveted looks came in October 2025, when she wore a $750 Wiederhoeft skirt with a matching bustier top on Late Night With Seth Meyers.

Keep scrolling to see all of Swift’s best skirt moments — and find out how much they cost:

One/Of Top & Skirt (similar top & skirt), Adam Lippes Bralette (old, similar here), Savette Bag, Roger Vivier Pumps

Late summer skirting walks the line between ease and structure, bringing movement to the everyday. Breezy poplins, pleated cottons, and softly structured linens come into their own now, styled with something as simple as a tee or something unexpected like a lightweight knit or tailored vest. These are the pieces that don’t chase attention but quietly hold it, offering just enough shape, sweep, or sway to feel intentional. Below, a selection of skirts that speak to this in-between moment, transitional yet not hurried, casual without leaning undone.