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Does make it trickier if you ware leaving from a warm country to the hot Caribbean for Men’s jackets but not impossible to go carry on if you hang for wrinkles. In Alaska, I did dress pants with twinkly tops. Summery dresses can pack up thinly. Consider, but if you go with large cases, make sure everyone divides their wardrobe evenly between the two in case one gets lost and take carry one with swimsuit, personal items and a change of clothes to make sure all bases are covered!