Island Hop.

(Denim Jacket – similar here; Urban Outfitters Vest; Tulle Dress; Target Sneakers; Leather Backpack via TJ Maxx – similar here)

Dressing for a day trip like this one presents a few challenges.  Since we had to carry everything for the day, I wanted to pack light and keep my hands free (this leather backpack – originally purchased for our cross country road trip last year, once again proved handy).  And because we left early in the morning with overcast skies, but the forecast called for sun by the afternoon I needed light layers (this vest, last seen here, is one of my favorite multi functional pieces) that I could shed throughout the day.  And finally, I needed something that was presentable enough for breakfast at a local island restaurant and window shopping in town, but forgiving enough for a day filled with walking and exploring.  I found a balance with an easy lightweight dress (a simple shape and elastic waist make this particular piece super comfortable but the print and color dress it up a bit), my trusty denim jacket layered under this utility vest and a simple pair of sneakers.  As for the island, it didn’t disappoint.  These pictures barely do the beauty of secluded nature, historic monuments and vivid oceanfront scenery justice.