Once you arrive at your destination it's a countdown. Do I have enough clothing to make it through? Aside from the obvious running out of underwear problem, there are other pitfalls- on vacation you tend to do more things that get your clothes dirty than in your day to day, but your clothing supply is more limited, leading to difficult choices.
The starkest choice really comes down to this- how many times am I going to wear this not-completely-clean thing? This pair of shorts I wore yesterday- I wore them to breakfast and from 3PM to 6PM and again from 11PM until bed. Do I put them on again this morning? How about this t-shirt? I didn't put it on until the afternoon but it got a little wet around the bottom. Wear it again or not? Or workout clothes. You can't bring a fresh pair of workout clothes for every day (Girl note: Well of course you do!).
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