When you arrive on a Caribbean Island, the feel of the sun, the smell of the air, and the slower pace of everything instantly signals you to relax and be comfortable. So a gal can really wear anything in the evening from shorts to jeans, to sexy little dresses. As for footwear, ‘wedge’ sandals are a popular choice, in addition to flats of any kind, and even booties.

On our recent trip to Turks and Caicos, here are a few of my evening outfits with some of the back stories…

This yellow silk dress was perfect for the island – the lightness, the color, the bohemian feel…I added the leather belt with a brass elephant buckle and carried a multicolored scarf as a wrap…

The dress and earrings were two of my lightning fast purchases at Pure Soul on Shelter Island (NY) last year…sure wish that the shop was not in such a remote location…if you ever happen to be passing through, don’t miss it!!!

This is another dress from Pure Soul, Camilla brand…it is much more impressive in person – vibrant silk fabric encrusted with rhinestones, in a flattering wrap style…my intention was to wear this with high gold platforms, but I had badly sprained a toe earlier in the day and there was no way those shoes were going on…fortunately I had a comfy gold flat with me – always wise to pack extra!

Here it’s all about the color – a simple hot orange dress by PINKO that I previously wore in NYC with white sneakers…this time I went edgy with Rag and Bone booties. Fyi, one night I wore these boots with shorts – yes, boots with shorts, and yes, boots in the Caribbean!

Can be breezy at night, always good to have a wrap…

This may look like a bit much for island wear but it was New Years Eve and we were going to a big bash at our hotel…dress is by Free People, under $100…I had originally bought a different sequin dress online (also by Free People) but it was a very boxy fit and not at all flattering on me…they easily accepted the return in a local store and directed me to this simple slip dress which came in many different colors…a necklace by Julie Miles was the perfect finishing touch.

So that’s four of my recent vacay evening outfits…as for the other four nights – I wore shorts a couple of times with fun tops, distressed white jeans with a sequined cami, and a boho black maxi dress…the consistent theme with the exception of the one night: no flats. As I always say, ‘when the sun goes down, the heels go up’!   Yeah, even on the islands… 😉

Do YOU have a vacation coming up? What’s your choice for evening wear?