Today I'm packing for our winter vacation in the Caribbean. We have been going to Jamaica for the last three years but this time we are going to Turks and Caicos (very Jenna Lyons, I know, but the excuse is that it's the only place besides Jamaica where there is a resort with a Sesame Street kid's club and entertaiments. And I don't mean TV. I mean a real Elmo and Co.).
We leave on Saturday morning very early (or maybe I should say Friday night very late as our flight is at 6.50 in the morning and with the new security policies you're supposed to be at the airport three hours earlier), so everything must be ready by tomorrow late afternoon.
I have to say, this is one of the few times where I'm not stressed about packing (maybe also because I'm stressed about something else in my personal life). Because we have been going in the Caribbean for years now (being close to the Caribbean was one of the "selling points" of moving in the US for me, I am such a beach person) I master the art of packing for an all-inclusive beach vacation and over the years I have put together what is for me the perfect beach resort wardrobe. I love to buy something new each year (it's part of the pleasure and my husband is always willing to give me a budget for this) but anything that I buy especially for this type of vacation must follow a simple rule: it must be suitcase-friendly, meaning that I don't need to worry about wrinkles, and it must take as little space as possible in the suitcase.
This year I bought two new pieces. The first one is the bikini that I found at Lohemman's last week. Rule number one when buying a bikini: you must like it when you're trying it in the fitting room already. If you're buying it hoping that it WILL look good with a tan and after loosing a few pounds, you should probably leave it at the store. You must feel good and body-unconscious already in the fitting room. Tough rule, I know, but I find that it's the only one that works. Now, I know that there are people (including good friends of mine) who only buy a new swimsuit when they really need it because they can't justify the cost per wear (and also because the don't like to shop for swimsuits for the reason mentionned above). However, I think that the memories sealed in a family vacation pictures are priceless and well worth the purchase of a new swimsuit for the occasion. This to say that I didn't really NEED a new one because my old ones still fit but I'm extremely unhappy of my vacation pictures in my Jcrew bikinis last year (it was my first time purchasing Jcrew swimwear and, I think, the last one).
So here is my new bikini:

It's from the brand Tibi and normally it would have costed $200 but I got it for around $50, thanks to Lohemman's democratic prices. If you ever come across this brand online (I remember seeing a sale on ideeli last year), you should know that the fit is really small. The bottom is a size Small but I think that a Medium would have been better and the top is Medium (a little bit loose but the S was cutting across my breast). Honestly I have no idea of who can fit in their XS.
My other new acquisition (and first easy piece to put in the suitcase) is a "resort" black dress. I have always struggled to find the perfect black dress to take on vacation with me. You definitively don't want to wear something like a little black dress on a beach vacation, but sometimes you want to wear a black dress that is not too casual-looking. I finally found an evening dress with a beach feeling to it. It's from the brand Calypso, which is one of my favorite resort brands, and the "metallic rope" neck is the detail that makes it special and beach-appropriate:


It's in pleated silk taffeta and it's wrinkled by design (very suitcase-friendly).
I have another dress from the same brand that I bought last year and responds to the same criteria:

It's the perfect dress that you can wear from the beach to the pool to the restaurant in the evening (it also works worn as a tunic over jeans), and it's coming with me this year too.
The third piece is this maxi-dress, another Lohemman's find from last year (it was very cheap but it's a Pucci-worthy silk):


Nothing easier to pull on and it photographs very well. See it "in action" last year in Jamaica with ... Cookie Monster (this is one of my favorite vacation pictures ever but I have just noticed that it looks like Cookie Monster is touching my breasts. I promise I didn't feel anything):
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This year I'm also taking his little sister, that I bought later in the year (same dress, different print) and you have already seen in a post back in the summer:

Last, an old favorite of mine, a DVF wrap "jungle dress". I bought this dress many years ago at a sample sale and a pregnancy later it still fits. However, I only wear it on vacation because as you can see the neckline is very low and I wouldn't dare to walk around like this in the city (but on a Caribbean beach is another story):


From the following pic you will understand what I was saying about taking as little space as possible in the suitcase:

That leaves plenty of space in the suitcase for the other beach essentials (a pair of shorts, a pair of white linen pants, a cover-up or tunic, a few solid tee-shirts, a beach sweater, a sweater and a pashmina for the evening, two good books and tons of sunscreen) and for my daughter's clothes and toys. Now that I got to share my suitcase with her, it's even more important that I limit myself and thanks to these 5 easy pieces I don't need to make a compromise between being beach-chic and overloading my suitcase (and husband is happy too).
Do you have any packing secret for a beach vacation that you want to share? Do you like to shop for resortwear?