I figured out how to get the elastic over the heels: put the doll's toes in first, then hook the elastic over your finger and pull it up and back as you slide the foot forward. Then lift your finger over the heel as you slide it out of the elastic, and it's good!
Also, here's lots of pictures. The white skirt is from the Tennis & Golf Set for Dolls + Book, which was released at the same time.
The pants are only a teensy bit see-through! The dark bikini bottoms are worn under the trousers in this picture, but you can't tell - the dark areas are actually shadows.
These sunglasses didn't fit the Josefina mold at ALL. The arms bent outwards at the temple and they rested around the eyebrows rather than on the nose! I tried a bunch of different tricks to get them to fit like they're supposed to, to no avail.
ETA: Photograph of the sunglasses on a Josefina mold (my Beatrice, #28):
Also, the outfit on a medium-skintone doll (again, Beatrice):
I hate the Bikini. It shows the tag, and it's a pain. Love the pants though. They aren't very summer looking since they are pants not shorts, but they are amazingly easy to roll up into caprices (the computer corrected this, not sure if I spelled it right). The flip flops are amazing!!! As well with the shirt, one of my favorite shirts! The hat makes it all for me.
I only have the partial outfit so I am only reviewing the shirt, pants, and shoes.
Shirt: Pro: I think it is really cute looking and I love the color combination. I like the fact it has a lower scoop neckline and I like the little knot detail at the bottom. I have ended up with a lot of t-shirts in my collection so it is a nice change. Con: I wish it was a bit longer because my doll's stomach shows easily (which isn't wrong but I prefer longer shirts). I also have an issue with the bottom hem of the shirt flipping up constantly. I'm wondering if the previous owner of this outfit machine washed and dried the shirt and pants so that may be my issue.
Pants: Pro: They are well made and sturdy. The back is elastic so you can just slide them on. The fabric has a stripe effect. Con: I don't really have any cons. Just style preferences. Im not a huge fan of the length. I wish they were either shorter or a little longer. It looks like they were meant to be long pants but my doll out grew them. Perhaps I am pulling them up to high....
Shoes: I don't have much to say. They are cute and it is nice to have another pair of sandals in my collection to mix and match with. They are sturdy and the elastic band over the heel works really well at keeping the shoes on. Although, I would be wary of taking a doll out for the day in these shoes because they do come off easier than sneakers or ballet flats.