When buying medieval boots, look for authenticity, comfort, and durability. Prioritize leather construction with period-accurate stitching and soles—either turnshoes or nailed soles, depending on the era. Ensure the fit allows for walking long distances, especially if used for reenactments. Check for historical accuracy in style—like ankle boots, poulaines, or cavalry boots. Laces, buckles, or toggles should match the period. Finally, choose boots from reputable historical outfitters known for quality craftsmanship and materials.