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I'd use a few swipes of NARS Red Square to take this dress from daytime lounging to evenings out.
Tropical vacations are not the time to waste suitcase space on extra footwear. One very awesome, very versatile and (most importantly) very walkable pair of shoes are all that's needed. (Soludos—more on those soon!—not included!)
Also doubles as a bra. (Because when it's really hot, I just can't with those padded cups.)
Stays out of the designated laundry duffel a little longer than white. (And by day four, that's a very importantly quality to have.)
Instead of flips-flops, I always wear these on the beach. That way my feet don't get burned by too-hot sand.
Pretty much every piece Isabel Marant made this season would work for a trip to Mexico. But since I can't bring the whole collection, I'd start with this top.
Much like my rule for footwear, one (perfect) pair does the trick.
Prettier than the average beach bag, so it works as an oversized purse, too.
The term "arm party" is so spring break 2011, but the look has endured. 
When it comes to Montezuma's revenge, one must not take chances.