Editor’s Note: Featuring the good, the bad and the ugly, ‘Look of the Week’ is a regular series dedicated to unpacking the most talked about outfit of the last seven days.

CNN  — 

Style and substance rarely intersect in fashion. In fact, some of the most stylish garments in public memory were woefully impractical. The emerald Versace jungle print dress that Jennifer Lopez wore to the 2000 Grammy awards? It may have been the inspiration for Google Image Search, but it had to be taped to her body to prevent a wardrobe malfunction.

From the days of cumbersome cage crinolines — steel hoops skirts designed to exaggerate the hips and shrink the appearance of the wearer’s waist — to tightly laced corsets, clothes (specifically those worn by women) have impeded comfort and free movement throughout history. Perhaps that’s why it’s so exciting when a garment is equal parts functional and flattering.

Taylor Swift is seen on June 26, 2023 in New York City.

Such is the case with the skort, the sartorial amalgamation of a skirt and a pair of shorts. This week, the hybrid garb has been spotted on Taylor Swift not once, but twice.

While out in New York on Tuesday, the award-winning musician paired a baby blue skort from Free People with an oversized striped shirt from luxury label The Row. Its form was typical, featuring a hidden pair of shorts underneath the skirt for an added layer of modesty. The anatomy of a skort can also follow that of a reverse mullet — party in the front, business in the back — much like the one donned by Swift the following day. The denim number resembled a wrapped mini skirt upon first view, until the singer-songwriter turned around to reveal the seat of a pair of shorts.

Taylor Swift is seen on June 27, 2023 in New York City.

In western culture, skorts date as far back as the 19th century. They were then referred to as “trouser skirts” and worn primarily by early female cyclists. In 1890, the US experienced something of a bicycle boom — the country was smitten with the two-wheeled technology, with clubs dedicated to the trendy sport popping up nationwide. Bikes allowed the masses to travel independently as they pleased, and the autonomy suddenly afforded to women was significant. It was a key moment for women’s liberation, emphasized by a necessary revolution in clothes: To avoid injury and ensure proper riding, bikes required women’s hemlines to be shorter, their skirts less voluminous and in radical statement against social norms, ankles to be exposed.

Spanish tennis player Lili de Alvarez shows off her divided skirt at the North London Tennis Tournament in Highbury, London.

Since the 1800s, skorts have continued to be an essential garment in women’s sports. Today, they’re most closely associated with tennis, often worn on the court by pro-athletes Venus and Serena Williams (the latter has worn many iterations, from a controversial denim Nike skort in 2004 to a lilac tulle skort designed by Virgil Abloh in 2018). Fashion has long been inspired by the sport. In 1931, French couturier Eliza Schiaparelli designed a skort for tennis star Lili de Alvarez who, Vogue wrote at the time, “was well known, not only for her tennis, but her extremely chic appearance on the courts.” No doubt “Challengers,” director Luca Guagandino’s upcoming courtside comedy-drama starring Zendaya and outfitted by Loewe creative director Jonathon Anderson will feature a sleuth of stylish skorts.

In this way, Swift’s serial support of skorts might be ahead of the curve. And for the purists who reject the idea of melding garments, 2-in-1 fashion is as ubiquitous as trouser pockets and raincoat hoods.