Choose black or brown: If you are working with limited space, I suggest you choose a color scheme. He will need at least one classy outfit for any vacation, so choose either black or brown dress shoes/belt. Then, match all his casual clothes to that color so he can dress everything up or down without worrying about looking like a homeless person.
Roll his clothes: The easiest way to cram a bunch of crap into a carry-on is to take all his t shirts, stack them on top of each-other and roll them into a burrito. Pack them vertically, and when you run out of space squeeze the rolls tighter together. This should be pretty easy since he probably won’t need more than one pair of jeans (unless of course, he’s gay).
Know where you are going: If you are traveling to sunny Florida, there is no reason to pack his jacket. If you are going to Aspen, he probably doesn’t need shorts. It doesn’t matter where you are going, he will never need cargo shorts; they take up too much space and don’t serve any purpose except to make him look like a middle-aged tourist.[ via ]
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