boat shoes

Sailing the Open Sea

Tristan grew up on boats and his parents have a vessel or three. We went out sailing one day a few weeks ago and it was delightful. In two and a half years of knowing this family, this was the first time I’d ever been out on one of their boats. We just couldn’t get the scheduling to work. I’m so glad we finally did!

Just so I wouldn’t be caught off guard, I started gathering outfit inspiration months in advance. I needed to be prepared at a moment’s notice!

First, I consulted our Forefathers (click on images for source):

Sailing Inspiration 4



38. sailing habituallychic

Grace Kelly:


Grace Kelly

The Kennedys:


5. jackie kennedy sailing habituallychic

16. kennedys sailing habituallychic

Then, just to cross my Ts and dot my Is, some general Pinterest and Google research:

Sailing Inspiration 3

Sailing Inspiration 5

Sailing Inspiration 2

Sailing Inspiration


LOVING these yellow coats – waterproof but still fun!




This gal even managed to get Chanel into her sailing look:


Here’s a cute look, but I don’t know what woman would wear that skirt sailing… that thing would get blown up by the wind in .132 seconds. Not trying to moon the in-laws!


But I do love those shoes. I also found a Croc version that I love. People are so hard on Crocs. When I worked at Disneyworld, entire families would come in with matching Crocs. Then I finally tried some on, you know, for commuter shoes. THEN I was hooked. And that was when they were still the slingback ugliness! It’s my dirty little secret.

But these little darlings, now just $25, I would wear with pride.


Look at this video that shows them in action… with a very chic sailing outfit, I might add!

And Tristan is WELCOME to dress like George Clooney any day.

2. george clooney sailing habituallychic

Here’s another man look I love:


Stay tuned for the next post which includes the final outfit and some other shots from our sailing trip!