When packing for Costa Rica, I planned my whole color scheme around pink, blue, and white. I did this based on items I already had and pieces I had ordered, like the two dresses I wore for dinners out. Both of those were new and I was dying to wear them, and I figured if I tossed in a hot pink scarf, I'd be good to go even if the nights were cooler. Everything else just flowed from there. Here's what I packed, and then you can see some of the outfits below:
Three dresses: chambray t-shirt dress, white embroidered dress, blue maxi (didn't wear)
Three shorts: navy chinos, white denim, blue jean
Three tanks: navy layered (similar), white flowy (similar), pink and blue patterned (didn't wear)
Three tees: pink, everlane navy, gray graphic (similar)
Three shoes: Crocs wedges, tan & brown sandals (similar), hot pink Nike sneakers
Two pants: patterned lightweight joggers (similar), zella leggings
One sweater for travel (similar)
One scarf for warmth
It was nice knowing that either of my dresses (and even the blue maxi I didn't wear) could go with either pair of shoes - the crocs or the flat sandals - based on how dressy I wanted to be. And of course, I brought a few different swimsuits - one that goes together and is reversible (top pic) and then a pair of black bottoms with two different coordinating tops (bottom pic) for beach days. I tossed in a navy cover-up, too! I also took my Eddie Bauer floral backpack, which packs into one of its pockets and is on sale for only $15, to use for the beach. That held my insulated water bottle, sunglasses case, sunscreens, and my kindle.
I only wore pants for travel. On the way down there, I wore my tennis shoes, leggings, tank, sweater, and scarf. On the way home, lightweight joggers, a tee, sweater, and scarf. Made for easy adding/removing of layers as needed based on weather and the temperature inside the airplane!
I ended up not needing nearly as many outfit combinations as I could have created, so nothing really got worn more than once, other than the shorts I brought. Frankly, that worked out well, since I had packed in a small carry-on anyway, it wasn't like I packed too many things. It was comforting knowing I had other options if I needed them.
I also, of course, took a few pairs of sunglasses - two that I've paid for from DITTO because I fell in love with them, and then my current borrowed pair. My sister just signed up for her free first month using my code (WORKCLOTHES) and got her first pair of glasses and she's loving it. Go ahead and give it a try - if you're not into it, you can cancel after the first month and you won't have spent ANY money - but if you like it, you can continue at just $24/month for all the designer sunglasses you can imagine. It's been so fun working with them and stepping outside of my comfort zone!