I do something similar as well: short lightweight packable puffer, hoodie underneath, then a long sleeve gauzy peasant blouse, light blue jeans that I can roll to the ankle, warm socks, Allbird tree sneakers. Then I peel off layers as I go. I'll have a bathing suit, pair of shorts and sandals as well as a sun hat in my bag, in case we can't check in right away at the resort. The hoodie comes in handy for cool evening breezes, the sneakers are summer style for hikes etc.
My other M.O. (assuming there's no snow on the ground) is to wear a sleeveless maxi dress with silk long johns underneath, hoodie or jean jacket, puffer over top, warm socks and sneakers.
For our recent trip to Australia (long haul flight) I wore leggings with a tunic length tank top, tunic length hoodie sweatshirt, and a jean jacket on top. No puffer -- as we went directly from house to taxi to airport. I had sandals tucked in my bag and just peeled down to tank top, leggings, sandals to sit around Sydney airport for four hours waiting for our connecting flight. It was hot in that airport! I also regretted not packing a fresh change of clothes as I felt disgusting after the long flight, especially since the kid behind me puked due to turbulence.
