This is every item of clothing I packed for five days in Jamaica. I love packing for warm weather because it’s so easy to shove everything in a carryon.
For once, I took a photo of my travel outfit. In this photo, it’s 5 a.m. in chilly San Francisco. My formula for the perfect travel outfit is always:
The scarf doubles as a wrap, and on the way home I wore the same outfit with an American Apparel circle scarf, which is magical and also works as a sarong or a shawl.
When I arrived for my four-hour layover in Miami, I was able to shed down to this, so I wasn’t sweating when I got to Jamaica. Jamaica!
I changed into sandals upon arrival and wore this to dinner on the beach.
The next morning, our first activity was a press tour of the Secrets Resort where we were staying. My striped shirt is H&M, the shorts are Rocawear (Shut up. I’m squarely in their brand demographic. Also! Those are on sale for $8 now. Go buy some so we can be twins). This outfit is my confused attempt at businessy tropical. Sort of. It turns out I didn’t need to worry much about the business part:
These shorts are stretchy. I’m pretty sure I wasn’t supposed to be on this trampoline, but I hung back until the tour guide had turned away, and bam. Actionwear!
This JCrew fedora is pretty much the best hat ever. I bought it in XL so it would look like I borrowed it from a cute boy. Then Bryan tried to wear it out of the store, and I had to assert.
Secrets has a dress code for dinner, so I changed into this American Apparel minidress. Actually, I think technically it’s a T-shirt. It’s nearly impossible to wear something in a way that’s sluttier than American Apparel intends, but I got it done y’all. The earrings are from Claires.
The dress is daring, but even more so because of the low back. I paired it with American Apparel shorts so I only appeared to be on the verge of exposure.
See? This is the same look dressed down a bit. These black shorts are identical to the navy pair I’m wearing above, by the way. Here the dress reads more like the shirt it actually is.
This romper was $9.80 at Forever 21. Are you proud of me for ignoring my impulse to iron it while on a tropical island? Thanks.
I wore this as a coverup, and I’m kind of amazed that it hasn’t fallen apart yet. Of course if I don’t hand wash it, the thing will probably shrink up to swimsuit size, but has pockets, so I threw caution to the wind.
I didn’t have a good pair of ruinable flip-flops, so I got these at Gap right before I left. I’m a big fan of metallic shoes for travel because they work with everything. These withstood the beach way better than I expected.
This is a vintage silk Vera scarf, which is my go-to wet hair solution. Pro-tip: If you have trouble with scarves slipping off your head, you’re probably buying polyester instead of silk. Fortunately, you can find silk scarves pretty cheap second hand. This one was $5.
I’ve had these Saltwater Sandals for years. They’re literally made for walking on the beach.
The playsuit is by Cotton + Candy, which doesn’t seem to be an Internet-friendly brand. If you live in the city, I got it on the Haight at X-Generation, and it is my new favorite thing.
And, aside from my underwear (five pairs, two bras — one strapless), and a black drapey dress I wore in Greece, that’s my trip in a carry on.