There was no specific set of clothes for medieval shepherds, they were among the very lowest class of peasants and wore their everyday clothing with a few additional items. Shepherds are frequently portrayed in Bibles since they feature prominently in the Christmas story - the inclusion of lowly peasant folk appealed very much to medieval congregations.
Apart from his usual linen shirt and braies (long, baggy underwear), woollen tunic and hose (separate leggings) and leather ankle boots a shepherd dressed for life outdoors in extremes of weather - he added a warm cloak, chape or hooded garment that might be lined with fur or made entirely of sheep's fleece, plus wrappings around his legs of linen cloth soaked in beeswax (cirecloth) to keep out the wet and mud.
Naturally he carried the tools he needed: a shepherd's crook (carried with the curved end downwards and the straight end in the hand) and a cow horn Trumpet for calling the sheep or his dog and signalling to other shepherds.
Modern shepherds also wear warm clothing such as padded jackets or winter coats, but their footwear is wellington boots (gumboots) and hooded cloaks are not included. Modern shepherds also carry their crooks upside-down (curved end upwards) as walking-sticks.
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Shepherds were among the very lowest class of farming peasants, but this did not mean they dressed in rags. They had access to homespun woollen clothes as well as very cheap, coarse wool material called burrel that was warm and fairly showerproof.
English shepherds are frequently depicted in medieval Bibles and books of the psalms (psalters) - they feature in the nativity story and this episode was a favourite one to illustrate. Shepherds are always shown with a hooded tunic, or a hooded cloak, or a tunic and separate hood; they frequently have cerecloth (waxed linen) bound around their hose (separate woollen leg coverings). Some are barefoot, others wear ankle boots or turnshoes; cloaks and capes of various types are often shown.
Cerecloth would keep wet and mud away from the woollen hose.
Shepherds often carried a cow horn for signalling and calling their sheep; their main tool was the shepherd's crook, made from a single piece of wood bent around at the lower end - this is exactly opposite to the way modern shepherds carry their crooks with the curve at the top.
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