Did cowboys wear vests? Yes, cowboys did wear vests, and they were an essential part of their wardrobe. Vests provided both practical and stylish benefits, offering an extra layer of warmth and protection during long rides in the wild. Typically made from durable materials like leather or wool, these vests were often worn over shirts or under jackets. They allowed cowboys to carry tools, such as knives or small firearms, in the pockets. A cowboy’s vest was not only functional but also a symbol of rugged individualism, adding to the iconic look associated with the Old West.