How did shepherds dress in the medieval times?

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.

See links below: