What to Wear on Harbour Island

Last week, Town and Country magazine posted this article about Harbour Island, which contained a link to a previous post where the author wrote about what she wore on her recent visit:  Tory Burch tunics, vintage dresses, Oscar de la Renta earrings... yeah, that's not how I roll. It's an elegant but casual island, so the idea of showing up for 10 days with a load of suitcases packed full of designer clothes seems ridiculous to me.  Maybe if you're Marie-Chantal...

That being said, as a dedicated carry-on only packer, I have made some straight-up hideous sartorial choices, especially on a trip to Italy as admitted here.  I've gone excessively casual on HI before as well (if you saw me at Cocoa Coffee House or Bahamas Coffee Roaster, I may have been in blue flowered pyjama bottoms. Sorry about that.). This year, I am planning to do a bit better. I'm still not breaking out my Tory or DvF, but I'm upping my game from the too-casual wear of the past.

I bought this dress from Banana Republic:

Better than sweats...

It flows, covers my knees mostly (I'm shorter than the model, of course), and it feels just slightly dressed up.  HI is a casual place after all.  I'm not bringing pumps like in the picture, which don't look right with this dress in my opinion.  I have a pair of old Prada sandals with about a 2" heel that should work.  Only problem is I'm running out of space in my luggage!

It would be easier if I could fly down dressed the way we used to when coming home from shopping trips in Buffalo.  To avoid paying duty, my girlfriends and I would wear all our purchases.  I have crossed the border in 4 bras, 3 sweaters, multiple belts, and a jacket; layers so thick i couldn't put my arms down at my sides. Not sure this would work on a 3 hour flight, however.

I also picked up this from Zara:

Model is thinner than I.  Model is thinner than the average flagpole, but that is another matter.

It's "flowy" as well, which seems to be what I'm all about this year. These 2 dresses should cover me for dinners at The Landing, Rock House, and Graycliff (we're spending one night in Nassau to avoid the early flight out of HI).

For walking around Dunmore Town, and the rest of the casual day stuff, I have a few other longish dresses- a navy tank from Ann Taylor last year, a black racerback from Joe Fresh ($19!), and a few Old Navy dresses.  These are the kind that go best with flip flops or bare feet, and that you don't mind getting sand all over.  This is one of them:

$30.  Can't argue with that.

All in all, my carry on is full, as I have also stuck in there a one-piece swimsuit and a tankini, cover up, sarong, short skirt, Adidas yoga pants, some t-shirts, and all the other little things you need for 10 days spent on beaches or in nice restaurants.

As usual, I'll check my bag on the trip home.  It's ok if West Jet loses it; sadly, I won't be needing clothes like this in Toronto for another 5 &#%$&ing months.  Sigh...