Often when we jet off to a tropical locale, we’re leaving from a much chillier clime. The weather we’re met with is usually an improvement, but if we’re dressed for the cold, the transfer from plane to hotel can be most unpleasant.
I’m heading to Jamaica for the first time—I am on the plane as I write this, in fact, and the plane ride itself feels like a vacation because I am child-free. But the what-to-wear-on-the-plane conundrum was no easier, never mind the fact that I’ve been in this situation approximately 652 times previously. So this time I gave he situation some serious thought in an effort to both maximize my minutes of vacation bliss and hopefully help out some of you beautiful people.
Here’s what I’ve learned from those 652 trips (plus lots of trial and error and a little Googling).
1. Long Pants or Skirt
I like 100% cotton or silk jersey, loose-fitting pants with an elastic waist or a long skirt. Jeans will make you sad on a long flight, and it might get chilly, so don’t wear anything that exposes your legs. Don’t wear overalls, because the extra metal in the attachments will set off the security system (learned the hard way). A sleeveless maxi dress layered under a button-down shirt over it is also a good choice, but don’t wear a long sleeve maxi dress because you’ll eventually regret those sleeves, most likely. And I don’t know about you but I always make some sort of mess on the plane, so I always opt for black.
Apparently I made just such a mess on my last trip, because when I pulled out my go-to silk jersey maxi dress for this morning’s flight, it was blotched with some sort of white substance. I figured I’d spot clean it with a washcloth and it’d be fine in the morning. It was not. The splotches were muted but still obvious so at 6am had to come up with an alternate outfit (the lesson here being always have a backup!!).
I came down on a black jumpsuit purchased at Anna’s tag sale, which I’ve never before worn. It’s essentially the same as my maxi dress, except with pants, which means one important difference: I have to remove my shirt (thank goodness it’s a button up), and unzip the jumpsuit each time I use the bathroom. It’s hasn’t been a huge deal so far (and I’ve peed thrice already, in case you wondered), but an extra step, for sure.
I also make sure the pants or skirt are not too long—nothing worse than tripping over your own clothing while navigating the airport. The jumpsuit has elastic at the ankles, which I’m all for since they deliver the added bonus of preventing fabric from gathering on the bathroom floor, which I’m never for.
This one is perfect and simple (and cheap!):
Pendleton Eliot maxi dress, $41
This one is loose while accentuating the waist nicely (also a great price!):
Laurel Canyon maxi dress, $28
These pants are almost sweats but not, and they’re as close to perfect for traveling as you can get. That’s probably why thery’re almost sold out in black, but army green works just as well:
2. Tank Top
If you’re not wearing a maxi dress, wear a tank top as your inner layer. You will be so happy you can peel off your outer layers once you deplane. I would again go for black, but any dark, stain camouflaging color would also work well.
3. Button-Down Shirt or Light Jacket
Denim or chambray are perfect choices for this outer layer. Anything breathable and soft will do, and you can tie it around your waist when you get too warm. I like a longer version for a flowy, relaxed feel. Again, an army green shirt would work here as well.
Another option here is a light jacket that you can combine with other outfits at your destination.
4. Slip-On Shoes
Today, remarkably, TSA did not require us to remove our shoes at the security checkpoint. Nevertheless, I was wearing my Birkenstocks with socks and I care not about silent judgements from fellow passengers. In case our shoe-removal reprieve was an anomaly, it’s probably still best to wear slip-on shoes to the airport. Socks are important so you don’t have to walk on the dirty airport floor in your bare feet, and to keep your feet warm on the plane. You can always take them off and stash them on your bag when it gets toasty. White Birkenstock Arizona, $100
Even if it’s a lightweight silk scarf, like mine by Centinelle, it can ward off a chill by tying it around your neck or placing it on your lap where it can also provide momentary respite from any travel discomfort because it’s so cute.
Mine is a leather one from Madewell. It has one large compartment, a zip pocket, and more slots for cards and bandaids and hair ties. Plenty of room for small purchases, extra shoes, scarves (see above) computer, whatever.
Madewell transport tote, $168
[Photo via Yoann Boyer via Unsplash]