When is the best time to buy skis and ski equipment?

The best time is when you find what you need and want at the price you are willing to pay. Some areas also rent helmets so consider that. Many ski shops have major sales going on right now. Clothing styles do change so the price is dropping but so is the selection. About the rest of your gear, buy the best fitting boots that you can afford. You will use them for several years. Sometimes there are ski shows and ski swaps in the fall that have a large selection of equipment and clothing. Many happen around Labor Day so save your pennies and do some research. Also check the rental shops for season rental returns and demo gear that was used last season. Also get to know some ski Patrol and instructors, they may have sources for last season gear or have used gear that might fit you at a low price.