I seem to always either overpack or under pack when I'm going on trips; what are some packing strategies that can help me avoid this problem?

Writing out a list is a big help. Look at the weather before starting to pack and arrange your wardrobe that way. I like knowing the amount of days I'm going and cutting that in half by how many pieces I bring (8 days, 4 bottoms 4 stops) to mix and match. Map out what outfits to wear which days so you make sure to utilize every piece you pack.
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