My Vacation Dressing Philosophy

Returning to Harbour Island with our baby boy has been such a dream come true, and on our second trip it's even better than I remembered. The weather has been perfection - in the high 70s and sunny everyday, honestly the instant we stepped off the boat onto the dock I felt relaxed. Harbour Island's nickname is "Home of Friendly People" and it's so fitting, everyone - locals and visitors - are warm and chatty. (Sometimes surprisingly open about personal details?! Ha!) I believe it's in large part why Harbour Island feels so relaxing, there's a social code and expectation of reciprocal warmth and courtesy that just puts you at ease here.

I've been getting a couple questions about how I plan my outfits for trips like this (or if I have a stylist - ha!) and my magic formula has been wearing dresses paired with elegant, neutral accessories. Each dress is easy to wear so I can feel comfortable whether I'm shopping, dining out, or chasing my baby boy. But above all, when I get dressed I think of what is appropriate for the setting, and even "will what I'm wearing enhance the experience of others around me?"

This is not about dressing expensively, or even stylishly, but dressing in a way that supports the ambiance of the experience. Are you on the beach with a cold drink and your toes in the sand? No shirt, no shoes, no problem! Are you at a romantic restaurant with water views at sunset drinking $28 cocktails? Well, that calls for something else entirely, and often times the way the guests dress can make or break the atmosphere of a place.

Our dinner at The Landing the first night of our trip is the perfect example. The restaurant itself is quite simple - most tables are outside on the deck, sure they have white tablecloths but the chairs are plastic. The elegance really comes from the people (and a really good menu). The staff are phenomenal, and guests really get dressed for dinner here. One couple didn't quite get the memo and arrived in performance apparel, with backpacks and zip off shorts with lots of pockets for carrying things, and hiking...sandals? I'm not even sure what to call them. Who knows, perhaps they were running late and couldn't change from their day - but I couldn't help but think how the entire dining experience would be different if everyone was dressed as if they had just come from a hike.

On a practical level, I find putting an outfit together so I look my best when interacting with locals and other travelers is much appreciated by others and is very helpful if you would like to be treated well on your travels. And now that we travel with a baby, and babies don't always adhere to social norms, I find that making an effort to dress appropriately and present yourselves well is even more important. :)

I've said this before, and I could write volumes on this, but simply put: when you travel, you are an ambassador for your country (whether you want to be or not!) and the way you dress and behave will lead others to create positive or negative impressions of your country - so it's worth the effort to leave a positive impression whenever possible.