You should know that I am an extremely light traveler. I hate to check bags or lug around tons of stuff I may or may not need. I am entirely no-nonsense when it comes to packing my suitcase. Just ask Kris. He always takes more than I do. I may or may not give him a hard time about it.
Because I love you, I'm going to pass on my knowledge to you. Before you know it, you'll be spending 5 days in Napa with just a carryon!
Step 1: The first thing you want to do before you start packing is make a list of the number of days you'll be traveling and the number of potential outfits you'll need - make sure to include any special events.
Step 2: Make a list of all the items you think you might want to pack/wear. This will help you get a clear picture of what you actually need versus what you think you need.
Step 3: Next, make outfits out of all the items you listed, and think about where you would wear said outfits. Make as many outfits as you possibly can from the items listed.
Tip: Jeans can be worn 2-3 times. So can tops if you wear them only for a short period of time on the first wear. For example, if you wear a top to a 2 hour dinner, you can totally wear it again.
Step 4: Last, eliminate excess items and items that can only be worn once. This will give you plenty of outfit options without making you pack items you don't necessarily need.
Tip: Consider wearing your chunkiest/bulkiest shoes to the airport. You'll have way more space in your suitcase without sacrificing what shoes you'll bring. For example, when we go to Napa I always bring boots, but they take up a ton of valuable suitcase space. I wear them to the airport/during travel. That way I have them, but haven't had to leave another pair at home.
Other things to consider: go through your daily routine in your head to remember items you might need or to help you identify items you can leave at home. For example, I always leave my eyelash curler and endless supply of eye shadow at home. I can get away with one shade while I travel. If you're hell bent on checking a bag, consider packing one check bag between your travel companions. Kris and I have been on 10 day trips and checked one bag. You'll save on baggage fees!
So there you have it, my tips on packing light. Bon Voyage, y'all!