Let’s face it, there’s always an occasion for patterns and textures (and dressy sneakers), but there is only one season when you can sport your woven straw, raffia, or rattan items: summer. From Memorial Day through to Labor Day, I get everything that I can out of my woven hats, shoes, clutches, and bags before saying goodbye to them—that is, until winter vacation, of course!

Nothing is more exciting than pulling out your summer clothes for a quick trip to the islands in the dead of winter. I once knew a man who lived well into his nineties. His secret, he said, was to always have a ticket to go somewhere. You always need to be in anticipation of something; you need that daily treat that you look forward to—morning coffee, a 3:00 PM sweet treat, an evening cocktail, or a good book—and something grander, like a fabulous vacation planned for March.

So, in that spirit, I have six more weeks of splashing about in my summery clothes, and my new favorite woven mule: The Traveler sneaker. Then, I must plan to take them out again for a tropical spin this winter. Just one problem: should I go somewhere I’ve never been, or should I go to a place I know I love. What do you think?