The proof of the packing pudding is in the wearing. On Day One in New York I was worried that I was too strict a suitcase mistress.(see post on packing)
With muggy (humid) heat of up to 102 degrees, followed by torrential but warm rain, I was using up the t-shirts and tanks very quickly. I learned that a sleeveless, thin, loose dress looks and feels better than shorts and a top. The most successful dress was a PJK lilac shirt-dress from a linen and nylon mix, and worn with the belt from my Sanctuary khakis. I washed it twice (promise) and wore it all over town. Proof above.
Also sterling was my denim Seven For All Mankind dress, which looks tight at the top but is nice and stretchy, plus bubbly in the skirt part.
My trusty stretch slip-on sandals from Sayulita in photos above are the colour of New York grime and not the least bit glamorous but lasted me five hours of walking every day. Bit Mumsy but....just do a Nietzsche and embrace your fate. Don't ever be tempted to wear new high shoes unless for a meal via a taxi.
What are your packing provens? I want to hear from you!