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.

This little red dress is one of those outfits guaranteed to make you feel happy. I got it at H&M for ten bucks. When saw the price tag, I think I may have howled at the sky in triumph. It’s poly-so it packs like a dream, even with all the ruffles.

In the morning I set out on a long walk in my sneakers and dress. It turns out the men of New York are very verbal about their appreciation for red dresses. My favorite exchange:

-That’s a real pretty red dress.
-Thanks.
-You gotta get yourself some nice stilettos to go with it though.
-Why don’t you get some stilettos to go with yours?
-…Bitch.
-Uh-huh.

The jacket is also H&M, my shoes are Puma. It was sunny and warm when I started out, and pouring by the time I arrived. I bought this umbrella along the way.

Here’s a blurry close-up of the shoes. I wasn’t sober when I took it, and I had just spilled bourbon on them. Sorry, shoes.

I wore this into Brooklyn for drinks, and it was also my traveling outfit for the next day. The shirt is Old Navy, the Jeans are Express, and my scarf is vintage.

The only thing I packed that I didn’t need on this trip was a cotton robe to use on treks to the communal bathroom at the Jane Hotel (they had robes in the room). I wore a cotton knit sundress to bed, in keeping with my philosophy of packing double-duty jammies in case I need an extra outfit.

Turns out it’s way, way easier to pack for New York in Spring than in Winter. I can’t wait for summer trips when you can take three weeks worth of clothing in a carryon.

Hey Laura, let’s take a moment to pause in the scenic parking lot outside our hotel at 2 a.m. because I forgot to take a picture of my outfit today.

Excellent. The jacket is thrifted, the purse is vintage, the expression is happy exhaustion. In real life, the blues are a little more harmonious than they appear under the parking lot spotlights.

This dress is a new favorite. I just picked it up at a vintage shop, and it fit like this right off the rack. Bam! it also rolls up into a little ball for packing and doesn’t wrinkle. Pow! Sock! Tights are from Target, and the little thing on my shoulder is a Fitbit. It’s like a pedometer that makes out with the Internet.

My shoes are also Target, and the pink purse has snaps on the side that let you make it clutch-sized, or larger like I have it here. My bracelet is from a museum shop in Buenos Aires, and so I especially enjoy it when people ask me where I got it.

I’m sorry for the silence yesterday, I’m in New York for the CM Summit and wifi has been tough to come by. But! Travel means Packing Light, and this time I thought I’d show you what I brought while I’m still here.

This is what I wore for the first day of the conference:

The dress was a steal at H&M, as were the safety-first neon tights. The librarian shoes are thrifted, and the bracelet is from a little boutique in Seattle. I look embarrassed in this photo because I’m about to start leaping around in the middle of the street.

See? I’d just come from champagne at The Algonquin with Laura and Liz, and I was feeling exuberant. Liz has me all caught up on The Real Housewives of New York City, so this trip is already paying dividends.

If you’ve been reading long, you already know the drill from my packing posts about New York and Puerto Rico. I don’t like to check luggage if I can help it, so I try to fit everything in a carry-on and my laptop bag. This is what I packed for two weeks in Greece. It’s eight outfits total, and my plan was to wear everything twice, but on different islands.

This is my favorite vintage dress. It’s cotton and it has pockets, purrrr. Great for visiting churches when I’m traveling, because it covers the shoulders and knees, but it’s cool and easy to move in. I can also plop down on the ground without worrying I’m flashing everyone, so it’s good for traveling with the toddler too. The shoes are my navy saltwater sandals.

Because it’s cotton, this dress wrinkles in the suitcase, so Bryan taught me a trick from his acting days. Head into your hotel bathroom with the dress on a hanger, turn the shower on hot, wet a washcloth, wring it slightly, and then pat the dress down. The little wrinkles will fall out with the steam, and the wet washcloth takes care of the big ones. I just put the dress on damp and let it dry on me, but you can also let it dry overnight.

The glasses are a drugstore purchase from years ago, the headband is an elastic 99-center from H&M. So useful, that I actually gave Melissa one when we were in Puerto Rico, because she lamented having lost the ones she picked up in San Francisco. You need one too. More on that later.

This is a simple black, drop-waist dress that I got for $7 at a thrift store when I was in college. On the plane, I wore this with a pair of black leggings, my trusty slip-off gold flats (see Puerto Rico post if you’re curious about those), a pale blue cardigan, and my swimsuit wrap worn as a scarf (the wrap also doubled as a blanket). Again, I’ve failed you in photographing my travel outfit. Don’t think I can’t hear you cursing me from here.

I think the dress is rayon, but it reacts to water like crepe — either way, it doesn’t really wrinkle. I bought the hat for 10 Euros in Santorini, because I didn’t pack a sunhat. Which was dumb. Be ye not so dumb, my traveling friends.

The purse is from Buenos Aires, the necklace is my favorite, a gift from Bryan purchased at Rare Device. I can’t believe I’m blanking on the artist’s name. One of you knows, I’ll bet. Let me know in comments, and I’ll update.

These are the same shorts I took to Puerto Rico, they’re Rocawear. The shirt is a men’s undershirt, Hanes I think.

The brooch is a long vintage silk scarf that I made into a flower shape and pinned to my shirt with safety pins. Because I am crafty.

Oh man this dress is so good. Also vintage, and unfortunately polyester — the yucky kind. I got past it though, and it’s great for traveling.

Bryan brought back the bracelet from a work trip to China. All my cool jewelry is from Bryan.

The gladiator sandals were my main shoes for this trip. They’re surprisingly comfy, though buckled a little loose in this photo. They’re from Delia’s, which is a teen catalog that’s great for accessories and trendy stuff that you only need to last for a year or so.

Speaking of trendy stuff that doesn’t need to last, here’s a $15 romper I bought for the trip from Urban Outfitters (Be careful, that site now has music! Ugh).

I told you a while ago that I like to pack jammies that can double as outfits, and these were supposed to be my jammies. I ended up wearing them almost more than anything else, the knit was crazy comfortable. Action wear!

The giant earrings are from a shop in Kentucky. They’re lightweight.

Back to that headband. I keep it in my purse when I travel because my hair invariably starts to look scraggly with wind and swimming, or I get too hot to wear it down. With this, I can pull it into a ponytail and use the band to clean up the stray frizz caused by humidity. It’s easy to do without a mirror, and the result is casual, but a little more polished.

This dress is by 25singles. The sleeves are constructed so I can push them to the front and back and wear a cardigan without any added bulk on my shoulders. Great for the city.

Greece is all about jumping for me, apparently. Anyway, you can see here how the sleeves only attach at the top, so you can arrange the folds for more tummy or bum coverage, as you desire. Genius.

The necklace is actually two necklaces from H&M, which I knotted together.

Here are those shorts again. The tank is by H&M, and is much fuller than it appears in this photo. I actually decided it was a little unflattering on this trip, and probably won’t be wearing it again. Such are the perils of seeing yourself in photos.

The shoes were a blog rec by Elizabeth from Browner Brown. They’re $17 Saniya Pointed Toe Flats from Target, and they’re rubber soled. They didn’t give me problems on this trip, but have since given me pinky toe blisters. Great with tights though, and I love the color.

The scarf is the same one I used as a brooch above. This time I looped it twice around my head, tied it on top, and tucked the loose ends under for an updated Rosie the Riveter vibe.

This is another vintage find. That green band has crazy giraffes and other jungle animals in play, which is spectacular. Super comfy.

The fish-scale belt is elasticized, I got it at a thrift store. The waist on this dress is a little high for me, so I like to define it a bit.

Sunglasses were on loan from Laura, as an Englishman had accidentally absconded with mine the night before, thinking they were his girlfriend’s.

This is my swim wrap, which I bought in Bali on my honeymoon. It’s essentially a large rectangle of linen with a random button and a random tie. I have to figure out how to wear the damn thing every time I put it on, but it’s great to travel with because I can also use it as a scarf or a blanket on the plane. It’s by Oka Diputra.

The back gives you a little insight into how it’s fashioned. Button at the neck, tie at the waist. Supposedly you can wear it like fifteen different ways, but I have no idea how.

Here’s my new La Blanca suit! I’m excited because I almost never buy new swimsuits. I may just be turning over a new leaf on that though. (Sorry this is a little blown out, my camera was on the wrong setting.) I got it on sale at Nordstrom.com. I like that it’s a sexy one piece, but I don’t feel like my boobs are hanging out. Also? Red! Which is the very best color for a swimsuit.

And that’s it! Here’s a shot of my suitcase.

I had so much extra room, that I decided to throw in my rollers, which was ludicrous. I used them twice and they made my bag heavy, which is a Packing Light fail.

You can also sort of see that I packed two things that didn’t get much play, a yellow turban purchased in Puerto Rico, and a white men’s button down to wear as a coverup (I wore it for sleeping instead). The red and white striped thing is an adorable $10 beach bag from Walmart, which I used a couple times as a shopping bag, and to carry home Hank’s gifts without crushing them. I also had a pair of black flip-flops, which got a ton of use.

Regrets? Well, the stupid curlers. Come on, Maggie. Also, I should have worn a sunhat on the plane. It took a while to find a reasonable one, and I don’t totally love it. Also, in retrospect, I would have thrown in three or four more evening dresses. We tended to wear casual clothes during the day, and dress things up at night. It would have been good to have a few more in the vein of my 25singles dress.

Also, I would have stuffed my busy husband and my cranky toddler in, because as fun as it is to travel with girlfriends, I missed those guys.

I was in Greece because Intel is sponsoring my Mighty Life List. Next week, I’m going skin diving in the Arctic Circle! Stay tuned.