I typically don’t dress up on vacation. So a pair of black pants is the fanciest thing I bring. I don’t bother with any accessories (no jewelry, scarves, etc.) I typically use only two pairs of shoes - sneakers for walking and something appropriate for the weather (either flips, flats, or boots) I wear the bigger of the two shoes on the plane (usually the sneakers or boots) so I only have to pack one small pair of shoes in my bag. Same thing with a jacket, I will wear the bulkier one on the plane and then only have to pack a lighter one (if needed at all - usually a rain jacket).
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