I aspire always to travel light. However it becomes a challenge when you have more than one destination, in 2 different climates, and when your trip calls for both urban and country wardrobe. And I am not a cowboy.
Shoes become an issue to contend with: they are bulky and heavy, but one must have proper footwear. It's impossible for any person with a sense of style to walk into a trendy coffee shop (and I do hope that's going to happen) wearing the same shoes one will be going to discover nature, and the reverse is even worse. Fancy shoes on a trail - there's no bigger offense to nature and fashion alike.
This is why I dislike packing and wait until the last minute to do it - deciding in advance what I will wear for the next 12 days, when I like to improvise every morning, simply feels wrong.
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