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Four Cornered hats - Source Images

Men in four cornered hats

Starting as early as 1480, the four cornered cap appears on the heads of various men of education and consequence, such as clergymen, senators, lord mayors, and physicians. Some versions had extensions that came down to cover the ears, and some had that extension tied up on top of the head, while others were symmetrical all the way around with no extension at all. 

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Detail from Omnium pene Europae, Asiae, Aphricae atque Americae gentium habitus engraved by De Bruyn, 1578
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Sketch of Thomas More by Hans Holbein. More was an English lawyer, social philosopher, author, statesman and councilor to Henry VIII, and Lord High Chancellor of England.
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Detail from Omnium pene Europae, Asiae, Aphricae atque Americae gentium habitus engraved by De Bruyn, 1578
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Nicholas Ridley (c. 1500–16 October 1555) was an English Bishop of London who was Martyred for his teachings and his support of Lady Jane Grey
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John Jewel, teacher at Oxford and bishop of Salisbury
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Desiderius Erasmus was one of the leading activists and thinkers of the European Renaissance Dutch Renaissance humanist, Catholic priest, social critic, teacher, and theologian. Portrait By Hans Holbein 1523
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Trevelyon Miscelleny 1608
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Detail from Omnium pene Europae, Asiae, Aphricae atque Americae gentium habitus engraved by De Bruyn, 1578
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Robert Abbot, Bishop of Salisbury unknown artist
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Anthony Bays: Hohenems Garden Party, 1578. Two different views of pink four cornered hats! The man facing forward is Mark Sittich von Hohenems Altemps (1533–1595) who was a German Roman Catholic bishop and cardinal. The man in profile is Cardinal Carlo Borromeo, a leading figure in the Counter-Reformation who was later beatified by the Catholic church.
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Detail from Omnium pene Europae, Asiae, Aphricae atque Americae gentium habitus engraved by De Bruyn, 1578
From the article:  Old hat; The evolution of your mortarboard 
By Angus Trumble | Jul/Aug 2008
Yale Alumni Magazine

The square revolution: 1500–1550
Within about 60 years, the first "square cap" or pileus quadratus was invented. Sewing four pieces of cloth together produced four "horns," or corners, and four seams or ridges on top. The point was to save time and money, because round hats required more cloth, more cutting and sewing, and more-difficult, radiating seams. The black or purple pileus quadratus was at first worn by priests and bishops, and is now, thanks to exceptionally detailed portraits by Hans Holbein the Younger, associated principally with Tudor England. There it denoted high status, perhaps because of the measure of protection it afforded senior clerics during painfully long services in drafty, unheated abbeys and cathedrals at the height of the Little Ice Age.
From the second quarter of the sixteenth century two further types of square cap diverged from the prototype. One, which was floppier and less sharp and thin, but always four-cornered, was reserved for certain senior Oxford graduates and English bishops and secular statesmen. It was made of softer, more expensive cloth, occasionally velvet, and was more generous, form-hugging, and therefore very comfortable. Satisfactorily, it covered the ears. Holbein caught it perfectly in his incomparable portrait of Sir Thomas More. A form of it was and still is worn by certain doctors of divinity.
The other form of early-sixteenth-century English square hat, plainer but still essentially four-cornered, was worn by undergraduates, choristers, and other persons of decidedly junior rank.
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