Seven years ago I went to Costa Rica for work and recapped my outfits here. I just got back from a trip for my relatively new job (which has a lot of travel) and I wanted to share my outfits and recap again.
Costa Rica is in their rainy/cool season, with temps in the low 80s and sunny in the AM, with cooler, rainier weather after about 2PM. The general dress is casual/smart casual, and I was visiting an office that is a vendor where we have near-shore partners who do contract work with us (basically) to have a workshop I was running to align on our 2027 priorities, etc.
Day 1 I didn't capture my plane outfit--the trip from NY is long, and it's my Comfy USA pants + a tank + my Krista Larson sheer layering tunic + my velvet and satin jacket and my go-to travel shoes: my Converse Commes de Garcon hi-tops.
Day 2 I took the day off as my team was still arriving so there was no meetings, and I had taken a weekend day to travel in. I wore a baum und pferdgarten dress (!!) that I found at the thrift store, to go to the office and get set up, meet everyone, and then I went to a place called Oxygen Human Playground (a mall) to shop and get lunch.
Outfit pic here I bought these bracelets and I pair of emergency slides as (not pictured) I changed into fancier shoes for the office/mall and they wound up hurting my feet--story of my life, sigh. I got a pair of brown Birkenstock-ish faux leather sandals at a place called "ekono" for about $30 and then just left them with a note to please keep/discard as they wished upon leaving the hotel--these weren't something I felt I needed to pack up and bring with me home. They worked fine but weren't a souvenir or anything.
Day 1 in office this Zara blouse I bought in Portland matches these Talbots pants almost exactly so I wore it as a set for my Day 1 outfit.
Day 1 dinner out with American colleagues I talked them into going back to this food hall I found my first time there and it was just as cool as it was years ago. Costa Rica is one of the single most gorgeous, calming, magical places I've ever been, the food is great, the weather is great, it's paradise. The food hall is called Mestizo Mercado, FYI. Highest possible recommend for both the country and the specific food hall. This is a vintage slip I both slept in and wore once as a dress with my Krista Larson top I hand washed (I found Tide sachets and they are a new MVP in being able to actually WASH items not basically rinse them in face soap, heh) so I could wear it again.
Day 2 by the way, this is the dress I wore in Dallas I didn't capture a pic of, with the same shoes I wore in Dallas. It's vintage and I had the hem let out slightly, although it's still a touch short for true comfort. We had a team dinner at a very nice (but still casual) restaurant and although I wish I could have gone back to the hotel to change, traffic prevented it--it took 1.5 HOURS to go 4 miles. For real. It's insane. I don't recall it being quite that bad last time but that was 7 years ago so...it may have gotten worse since then.
Day 3 this was the final workshop day. I adore the brand CORD and have two dresses and a blouse and if it was cheaper I would have TONS more. As it is, I pounce on sales.
Last day, plane trip home this is the basic plane outfit (I've worn this for multiple plane trips now)--Comfy USA pants (I will be SO sad when these wear out) and a tee, with a flowy topper. The tee is this Gef tee which has a really unusual texture and is heavy-weight ("heavy grammage" cotton).
I also got this pin which is based on vintage matchboxes, and this blouse from Mango, as well as this blouse but the second one is right on the edge of being too small so I may just resell/donate it; they were both on sale.
MVP: the slip! I bought a Newport News 100% silk slip from Poshmark or something and bring it to wear as a slip/dress and as sleepwear on trips all the time.
Overall: both dresses were a bit short or otherwise revealing (the CORD dress has a slit I need to reinforce as it keeps pulling open at the stitching) but dresses make for a very easy one and done outfit especially in hot, humid weather. I was particularly glad to be wearing my nicest option when on Day 3 I went back to the shopping area after work (near AC1 hotel--it has both upscale and chain shops) and was nicely dressed and not feeling dowdy or too-business-y.
I also got a Chanel eyeshadow in Duty Free and a couple small souvenirs but they were not "fashion" so I didn't include them here :)
I have reached a point with my wardrobe in general where I feel I can grab and go with almost everything, however. While I brought a dress + heels + a clutch for the dinner (that I didn't get to use) everything else was relatively casual. I have figured out that items with multiple purposes and layers are they key for travel and "day to night" which does happen for business travel (perhaps the only scenario where it still does in this day and age!)
Have you been to Costa Rica? What did you wear/buy? Share to us!