Yes. Danskos, properly designed clogs used for physical activities, may need a break-in period. Whether you get a waterproof or water repellent type is dependent on where the clogs are worn and what action they will be used for - from gardening to working in wet conditions. If you wear your Dansko around the house all day, your foot muscles should be well accommodated by the end of a week or two, and no break-in period would be necessary.