This past weekend, I was able to get away with John for a quick birthday trip to one of my favorite places: Nantucket Island. When I’m on Nantucket, I like to pencil in a few plans with friends and a dinner at Straight Wharf Restaurant, leaving everything else wide open. I’m not one for packing my vacations with commitments. If I feel like relaxing poolside all day, that’s where you’ll find me. If the mood to shop strikes, you’ll find me at Millie & Grace or The Lovely. So, when I head to Nantucket, I travel lightly with outfits that I know can transition from day to night. After all, a morning sail can turn into lunch with friends, and that can turn into clinking glasses of rosé as we toast to the sun setting on another lovely day . . . and before you know it, we’re all trying to figure out dinner plans. So, simplicity and no expectations are everything when it comes to my vacation mindset. 

I packed my Occasion sneaker and my Travelers for this little island getaway. The Traveler is an elegant, raffia mule that is so versatile—a must-have for the summer. The Occasion sneaker is a modern, romantic lace and leather slip-on that’s instantly everyone’s favorite shoe—so beautiful and feminine. Dressy sneakers are a vacation lifesaver! I can wear them poolside, beachside, dockside, and “deckside,” and can comfortably stroll the island looking effortlessly chic. I hate having to decline an invitation or interrupt the flow to rush home and change. On Nantucket, I want to be ready for any spur-of-the-moment invitation or meetup. 

Here’s a peek at my morning poolside look and a sneak peek into my bag of tricks. I carry the usual sun-care essentials and after-sun creams and serums, but I also pack a high-protein snack (we don’t want the bloat) and some chocolate-covered espresso beans (you never when you might need a little caffeine boost), and Advil. I can’t tell you know many times my little Advil pocket pack has saved my day or a friend’s. Depending on how I’m feeling, I might slip into The Traveler or The Occasion sneaker. And of course, everything pairs well with a glass of rosé and a breezy attitude!