Not Europe; I know how to do that. ; )
In March we are doing a two- week hiking trip in Patagonia, and I know exactly what to take for that, including boots, rain jacket, fleece, etc. there will be little room left in my 22" roller bag and daypack, so I need to minimize the clothes for the rest of the trip.
On the way down, we are spending 3 days in the Florida Keys, so I presume we will need warm-weather clothes and swimsuits. Then we fly to Santiago, Chile, where we have a day of sightseeing and spend the night. It will be hot and humid there.
On the way back, we have a night in Buenos Aires and will want to go out to a nice place for dinner. Then we fly to New York to spend a few days, which will include at least one nice restaurant dinner with family members.
So in addition to the hiking clothes, I will need warm-weather clothes and dress-up clothes. Thinking of two short-sleeve tees and a pair of capris for the Keys ( assuming it is all casual), a packable skirt for sightseeing in hot and humid Santiago, then paired with a dressy top and scarf for the nice restaurants in BA and NYC. I will of course have a rain jacket if it is needed anywhere.
For footwear, in addition to the hiking boots, I will need after-hike footwear--probably sneakers that can do double duty as walking shoes in New York--- and dressier shoes to go with the skirt---probably sandals I know I can walk long distances in.
Will that cover it? I know the weather can be anything in New York---it will be early April by then. But I have no idea about the Keys---I have never been to Florida. This will be mid-March. And since this is the only place I will want a swimsuit, I will take an old one and discard it there, rather than carry it along on the rest of the trip.
Thanks for you advice.