Outside Western cultures, men's clothing commonly includes skirts and skirt-like garments; however, in the Americas and much of Europe, skirts are usually seen as feminine clothing rather than men and boys to wear, despite having done so for centuries. While there are exceptions, most notably the cassock and the kilt, these are not generally considered skirts in the typical sense of fashion wear; rather they are worn as cultural and vocational garments. Advocates for the wearing of skirts by men seek to remove this gender distinction.

In Western cultures

Ancient times Skirts have been worn since prehistoric times. They were the standard dressing for men and women in all ancient cultures in the Middle East.

The Kingdom of Sumer in Mesopotamia recorded two categories of clothing. The ritual attire for men was a fur skirt tied to a belt called Kaunakes. The term kaunakes, which originally referred to a sheep's fleece, was later applied to the garment itself. The animal pelts originally used were replaced by kaunakes cloth, a textile that imitated fleecy sheep skin.Boucher, Francois (1987): 20,000 Years of Fashion: The History of Costume and Personal Adornment. New York: Harry N. Abrams Kaunakes cloth also served as a symbol in religious iconography, as the fleecy cloak of St. John the Baptist.The Bible: Genesis 12:4–5Roberts, J.M. (1998): The Illustrated History of the World. Time-Life Books. Volume 1. p. 84

Depictions of kings and their attendants from Babylonia on monuments like the Black Obelisk of Salmanazar show men wearing fringed cloths wrapped around their sleeved tunics.Rief Anawalt, Patricia (2007): The Worldwide History of Dress. London: Thames & Hudson. p. 22

Ancient Egyptian garments were mainly made of white linen.Barber, Elisabeth J.W. (1991): Prehistoric Textiles: The Development of Cloth in the Neolithic and Bronze Ages with Special Reference to the Aegean. Princeton: Princeton University Press. p. 12. The exclusive use of draped linen garments, and the wearing of similar styles by men and women, remained almost unaltered as the main features of Ancient Egyptian costume. From about 2130 BC during the Old Kingdom of Egypt, men also wore wrap around skirts (kilts) known as the shendyt, They were made of a rectangular piece of cloth wrapped around the lower body and tied in front. By the Middle Kingdom of Egypt there was a fashion for longer kilts, almost like skirts, reaching from the waist to ankles, sometimes hanging from the armpits. During the New Kingdom of Egypt, kilts with a pleated triangular section became fashionable for men.Rief Anawalt, Patricia (2007): The Worldwide History of Dress. London: Thames & Hudson. p. 25 Beneath was worn a triangular loincloth, or shente, whose ends were fastened with cord ties.Rief Anawalt, Patricia (2007): The Worldwide History of Dress. London: Thames & Hudson. p. 24

In Ancient Greece the simple, sleeved T-shaped tunics were constructed of three seamed tubes of cloth, a style that originated in the Semitic Near East, along with the Semitic-based word khiton, also referred to as a chiton.Rief Anawalt, Patricia (2007): The Worldwide History of Dress. London: Thames & Hudson. p. 88 The belted worn linen chiton was the primary garment for men and women.Rief Anawalt, Patricia (2007): The Worldwide History of Dress. London: Thames & Hudson. p. 89

The Romans adopted many facets of Greek culture, including the same manner of dressing. The Celts and Germanic peoples wore a skirted garment which the historian Diodorus Siculus (fl. 1st century BC) called chiton. Below they wore knee-length trousers. The Anglo-Saxons, Normans, Franks and other people of Western and Northern Europe continued this fashion well into the Middle Ages, as can be seen in the Bayeux Tapestry.Koch-Mertens, Wiebke (2000): Der Mensch und seine Kleider: Die Kulturgeschichte der Mode bis 1900. Düsseldorf Zürich. Artemis & Winkler, p. 114.

Technological advances in weaving with foot-treadle floor looms and the use of scissors with pivoted blades and handles in the 13–15th century led to new designs. The upper part of dresses could now be tailored exactly to the body. Men's dresses were buttoned on the front and women's dresses got a décolletage. The lower part of men's dresses were much shorter in length than those for women. They were wide cut and often pleated with an A-line so that horse riding became more comfortable. Even a knights armor had a short metal skirt below the breastplate. It covered the straps attaching the upper legs iron cuisse to the breastplate.Tortora, Phyllis et al. (2014): Dictionary of Fashion. New York: Fairchild Books. p. 11.Koch-Mertens, Wiebke (2000): Der Mensch und seine Kleider: Die Kulturgeschichte der Mode bis 1900. Düsseldorf Zürich. Artemis & Winkler, pp. 156–162. Other similar garments worn by men around the world include the Greek and Balkan fustanella (a short flared cotton skirt)

Decline The innovative new techniques especially improved tailoring trousers and tights, which require more differently cut pieces of cloth than most skirts do in their designs. "Real" trousers and tights increasingly replaced the prevalent use of the hose which like stockings covered only the legs and had to be attached with garters to underpants or a doublet.Koch-Mertens, Wiebke (2000): Der Mensch und seine Kleider: Die Kulturgeschichte der Mode bis 1900. Düsseldorf Zürich. Artemis & Winkler, p. 130 A skirt-like garment to cover the crotch and bottom were no longer necessary. In an intermediate stage to openly wearing trousers the upper classes favoured voluminous pantskirts and diverted skirts like the padded hose or the latter petticoat breeches.Koch-Mertens, Wiebke (2000): Der Mensch und seine Kleider: Die Kulturgeschichte der Mode bis 1900. Düsseldorf Zürich. Artemis & Winkler, pp. 216–217

Though during most of history, men and especially dominant men have been colourful in pants and skirts like Hindu maharajas decked out in silks and diamonds or the high heeled King Louis XIV of France with a diverted skirt, stockings and long wig.Noah Harari, Yuval (2014): Sapiens: A Brief History of Humankind. Vintage-books. pp. 168, 169 The French Revolution and the Industrial Revolution changed the dress code for men and women not only in France. From the early Victorian era, there was a decline in the wearing of bright colours and luxurious fabrics by men, with a definite preference for sobriety of dress.Ribeiro, Aileen (2003): Dress and Morality. Berg Publishers. p. 169. This phenomenon the English psychologist John Flügel termed "The Great Masculine Renunciation".Ross, Robert (2008): Clothing: A Global History. Cambridge: Polity. pp. 35, 36 Skirts were effeminized. "Henceforth trousers became the ultimate clothing for men to wear, while women had their essential frivolity forced on them by the dresses and skirts they were expected to wear".Ross, Robert (2008): Clothing: A Global History. Cambridge: Polity. p. 59 By the mid-20th century, orthodox Western male dress, especially business and semi-formal dress, was dominated by sober suits, plain shirts and ties. The connotation of trousers as exclusively male has been lifted by the power of the feminist movement while the connotation of skirts as female is largely still existing leaving the Scottish kilt and the Albanian and Greek fustanella as the only traditional men's skirts of Europe.

Revival In the 1960s, there was a widespread reaction against the accepted North American and European conventions of "male and female dresses". This unisex fashion movement aimed to eliminate the sartorial differences between men and women. In practice, it usually meant that women would wear male dresses, i.e. shirts and trousers. Men rarely went as far in the adoption of traditionally female dress modes.

Some exceptions were the costumes of pop musicians. Mick Jagger of the Rolling Stones wore a white dress over white trousers for their 1969 Stones in the Park concert, while David Bowie appeared in a patterned silk dress on the cover of his 1971 album The Man Who Sold the World. Both men, particularly Bowie, experimented with androgynous fashion styles throughout the 1970s.

However, the furthest most men went in the 1960s in adopting feminine attire were velvet trousers, flowered or frilled shirts, ties, and long hair.

In the 1970s, David Hall, a former research engineer at the Stanford Research Institute (SRI), actively promoted the use of skirts for men, appearing on both The Tonight Show Starring Johnny Carson and The Phil Donahue Show. In addition, he was featured in many articles at the time. In his essay "Skirts for Men: the advantages and disadvantages of various forms of bodily covering", he opined that men should wear skirts for both symbolic and practical reasons. Symbolically, wearing skirts would allow men to take on desirable female characteristics. In practical terms, skirts, he suggested, do not chafe around the groin, and they are more suited to warm climates.

In the early 1980s, Boy George, lead vocalist of the British pop group Culture Club, brought androgynous dressing to a wide audience, wearing long skirts or dresses, makeup and long hair.

In 1985, French fashion designer Jean-Paul Gaultier created his first skirt for men. Transgressing social codes, Gaultier frequently introduces the skirt into his men's wear collections as a means of injecting novelty into male attire, most famously the sarong seen on David Beckham.Fogg, Marnie (2011) The Fashion Design Directory. London: Thames & Hudson. p. 165. Other famous designers such as Vivienne Westwood, Giorgio Armani, John Galliano, Kenzo, Rei Kawakubo and Yohji Yamamoto also created men's skirts.Fogg, Marnie (2011) The Fashion Design Directory. London: Thames & Hudson. p. 316. In the United States, Marc Jacobs became the most prominent supporter of the skirt for men. The Milan men's fashion shows and the New York fashion shows frequently show skirts for men. Jonathan Davis, the lead singer of Korn, has been known to wear kilts at live shows and in music videos throughout his career. Mick Jagger and Anthony Kiedis from the Red Hot Chili Peppers were photographed by Anton Corbijn wearing dresses.Corbijn, Anton (2000): Werk. Schirmer/ Mosel (Germany). p. 70 For an FCKH8 anti-discrimination campaign Iggy Pop was seen wearing a black dress and handbag. Guns N' Roses' singer, Axl Rose, was known to wear men's skirts during the Use Your Illusion period. Robbie Williams and Martin Gore from Depeche Mode also performed on stage in skirts. During Depeche Mode's Berlin period (1984–1985), Gore was often seen in public wearing skirts. In an interview with Pop Special Magazin (7/1985) he said: "Sexual barriers and gender roles are old fashioned and out. [...] I and my girlfriend often share our clothes and make-up". Lord Jamar of the group Brand Nubian criticized Kanye West for wearing skirts, saying that his style has no place in hip-hop.

In 2008 in France, an association was created to help spur the revival of the skirt for men. Hot weather has also encouraged use. In June 2013, male Swedish train drivers, whose cabins reached up to in the summer heat, wore skirts to circumvent and protest a ban on wearing shorts. The ban was subsequently lifted. In July 2013, parents supported boys wearing skirts at Gowerton Comprehensive School in Wales.