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:
comfy knit dress (ISDA and Co.) + leggings (H&M) + scarf (gift from Vietnam) + cardigan (H&M) + slip on shoes (H&M)
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!
After the Secrets tour, the Jamaican Tourist Board rounded us up on a bus to take us dogsledding and waterfall climbing (more on that later). My navy shirt and shorts are both American Apparel.
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.
This is me and JoAnna conquering Dunns River Falls. Apparently I now flex whenever a camera is turned my way. My bikini is American Apparel, and it covers stretch marks with aplomb.
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.
My Southwestern sandals are BC from Zappos, which is a lifesaver when you have two days to find shoes for your trip.
As you know, I always try to pack PJs that double as outfits in case something comes up. I wore this Old Navy tee and H&M shorts to bed, and also to hang by the pool.
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.
My excellent yellow turban is from a gift shop in Puerto Rico. I got it on the same shopping trip when I failed to convince Melissa to buy the stripper heels with the zipper up the back.
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.
You’ve seen this DKNY suit before. The outer skirt pulls down to miniskirt length or pushes up to your midsection. You’ll be glad to note that I didn’t wear this to dinner as a dress.
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.
This is what I wore for our tour of Rose Hall. I got this candy-striper stripe top at H&M. I wore it over a romper, but also as a coverup with my bikini.
I’ve had these Saltwater Sandals for years. They’re literally made for walking on the beach.
This is my favorite photo from the trip, taken by the very patient and talented Kate. (Holy, holy go check out the World Cup commercial she filmed for Puma. Goosebumps.)
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.
Mighty Girl 