Anonymous
Post 02/14/2026 09:31     Subject: Re:Another "dress me for the plane" Q: Flying from wintery DC to summery Caribbean (and back)
Anonymous wrote:I do this yearly. I wear socks and sneakers, capri leggings or capri joggers (light like Vuori), a tee shirt, and a sweatshirt. I dress my kids the same but in athletic shorts instead of capris. The walk from the car to the heated inside part of Dulles sucks but only takes 5 minutes. Then when we land, we take off our sweatshirts and tie around waist. Not difficult, and you typically want sneakers and a sweatshirt on the islands anyways for windy nights or for hiking


+1 to this, and we also do this yearly. None of us ever pack a coat.
Anonymous
Post 02/12/2026 17:31     Subject: Another "dress me for the plane" Q: Flying from wintery DC to summery Caribbean (and back)
I live in Canada and often escape the frozen wasteland for a tropical vacation. I always leave my car at the airport, with my jacket/mitts/whatever in the car. I wear a sweater, sneakers and only pack tropical clothes.

I can put up with a chilly few mins to the actual airport/coming back. Usually when I come back they've already warmed up the car too so that's helpful!
Anonymous
Post 02/12/2026 17:29     Subject: Another "dress me for the plane" Q: Flying from wintery DC to summery Caribbean (and back)
Sweatshirt and joggers (because they are cuffed). This isn't that hard.
Anonymous
Post 02/12/2026 11:14     Subject: Another "dress me for the plane" Q: Flying from wintery DC to summery Caribbean (and back)
Lately I've been traveling in maxi dresses and cardigans. I can wear leggings under when it's cold and easily slip them off. Ideally both the dress and the cardigan will have pockets.

I used to wear wide legged pants, tee, and cardigan but it was gross how they would touch the bathroom floor.