Once you find a dry cleaning service that fits your needs and budget, the next question is how often should I schedule my dry cleaning services? The answer to that depends on your lifestyle and the needs of your family. If you are working in a suit and tie every day, you will need to schedule more frequent services from your dry cleaners. That number might be less in the winter and more in the summer since the temperature is warmer and people are more likely to sweat in their work clothes during the summer months.