Sometimes I dread packing so much that I am willing to forgo the actual vacation. Perhaps the worst packing of any kind is in preparation for a ski trip. Not only is there extra gear, but also it is gear that is quite cumbersome. Further, should you forget anything, it can really inhibit full enjoyment of your trip. Thankfully, after many years, I have managed to master slope packing such that it has become my easiest packing endeavor of the season.
First and foremost, prepare to ship your luggage in advance. Regardless of your travel mode, it is worth the extra bucks not to have to schlep all the heavy stuff with you. Moreover, it forces you to get the packing completed and out of sight days before departure. Hence, there are no visible obstacles between you and the mountain on travel day when the anxiety of air travel and all your other neuroses set in.
Second, consider size when determining which pieces of luggage to utilize. As far as the contents, most ski destinations are casual, even in the evening. Yes, I know you need to step up your game in places like Aspen or Gstaad. Just remember, you always want to appear to be effortlessly chic, not all yaya jezebel. One duffle, one garment bag, and a ski bag should do the trick.
Third, always work from a list. You can even use my packing list to check off each item as you load it into your luggage.
Fourth, hang all items on just two plastic hangers. The ones from the dry cleaners are thin and therefore perfect space savers. Then, place these inside a plastic garment bag (the free one you got during your last luxury shopping spree). Roll all other folded items in tissue paper. Place undergarments in Ziploc bags, all shoes and handbags in cloth bags, and your bags are packed!
Fifth, if you have the luxury to do so, pleeeease have someone unpack your shipped goods prior to your arrival. Most fine hotels and lodges offer this service. Ask the concierge and take advantage of these amenities. Having your stuff ready to go upon arrival is like adding an entire day to the ski trip. Truly life-altering (or at least vacation-altering).
See you on the mountain!