I’ve always wanted to learn to sail. During my dad’s last year of medical school at UM, Jackson Hospital was so chaotic that no one really knew if he was there or, say, floating on a sailboat. So, for the fields of no interest to him, he would go study on his sailboat in lieu of completing his rounds. All his crazy sailing stories have always stuck with me. I went out in the family sailboat for the first time with Kyle in Maine, and although the combination of rough waves and his questionable nautical skills induced a few minor panic attacks, I loved every second of it. It’s totally true that happiness is sailing your troubles away. That being said, I had absolutely no clue what to wear sailing– let alone on a sailing date. If you’re in a similar boat (pun intended), keep reading!

The question of what to wear on a sailboat hinges on two major requirements: comfy clothes and non-slip, closed toe shoes. The key is to be comfortable and capable of maneuvering around the sailboat easily. I knew that Sperry’s were arguably the best sailing shoes (if not also the cutest), so the question of what shoes to wear sailing was simple. As for the sailing outfit itself, I decided to keep it classic. I wore a Banana Republic rugby stripe tank top with white skinny jeans and Sperry Top-Siders. It was pretty chilly, otherwise shorts would’ve been totally fine, too. Keep scrolling to the bottom of this post for full outfit details! For more Labor Day outfit inspiration, you can also check out this super cute beachy look from my time in Kona, Hawaii last year.

If I could give one major caveat about what to wear sailing, it would be to not wear expensive and/or non-waterproof jewelry. I made the mistake of wearing my new Michele watch and almost had a heart attack. Never again! Shop the Look: Rugby Stripe Tank Top: Banana Republic (Out of Stock), Similar Styles Linked Here, $34 + Here, $74 | Jeans: Express, $45 (on sale) | Shoes: Sperry, $50-$95 | Bag: Tory Burch, $195 | Watch: Michele, $445 | Sunglasses: Fantas-Eyes, $22 Similar Style Linked Here, $17

If you’re still unsure about what to wear sailing in the summer, leave your questions in the comments! I’m still no expert, but I’m becoming more and more comfortable out there on the water. Speaking of sailing, my upcoming Labor Day could include lots of it. What are y’all’s plans for Labor Day? Anything fun? I’m a little nervous, since this is my first Labor Day in New England. IHelp!