What to Wear When: Sailing

Sailing is one of those things that invites all sorts of sartorial opinion, for better or worse. I suppose this is likely because so much of what we consider to be classic, preppy style is grounded in clothing that was historically associated with the perceived elitism of sailing; the lifestyle,  the socioeconomic status…all of these things were, and to an extent perhaps still are, strongly reflected in the clothes.

Photo Life

When it comes to the pursuit of the high seas however, things are changing. The classic styles once associated with sailing have been adopted (some might say hijacked, but that is a different post for a different day) by the masses. Classic, nautical styles are now available to us all in varying permutations.

This weekend, Himself and I took part in the opening of the West Highland Yachting Week festivities on our friends' boat. The weather was absolutely perfect on race day. So perfect that we came in dead last in our class, forgoing tactical navigation strategy for lively conversation against the backdrop of a leisurely jaunt through the waters of the Scottish West Highlands, a lovely pinot grigio, and some amazing makarel pate.  Sometimes it just seems a shame to tack the boat when you have this beautiful spread in front of you and a nice tailwind. Too much like work. That's how we roll.

Our rather relaxed approach to the event also gave me time to reflect on the whole experience from a self-proclaimed fashionista's perspective; what does one really need on a boat anyway? You are existing in a small space, in a mostly casual, if not downright outdoorsy environment (depending on the boat), yet there may be the odd occasion to have a lovely dinner out, boat-hopping at the marina, and other opportunities to socialise. You want to look sharp (as we always do), but not in the same way you might if you were at home or in the city. Me, I tend to stick with the classics; polos, a wool crew neck for night or when it is rainy or cold (most of the time…it's Scotland).  My ideal look is to still look like me, just my minimalist, sporty version of me; not some version of me that has pasted-on so much nautical-looking preppy stuff that I look like an extra from Caddyshack…no, just enough of a balance  to know that I can get salty and damp with impunity but still pull it together if need be.  So what does one really need in a pinch?

Waterproof Outerwear 

Though you can skip these in tropical places, the waterproof trousers and jacket plus wellyboots combo are a necessity in colder places, or when the weather is bad.  If you get invited on a boat and don't have your own, ask your host if you feel that you can. More than likely you will be able to borrow. 


                          Non-Marking Shoes                           

You don't have to go all old-school boat shoe here (unless you want to). Light-coloured soles that won't mark the deck will do. I love my converse. They have light soles, are comfy, and keep the classic clothes from looking too buttoned-down. It also won't break my heart if when they get wet. Leave the pointy heels at home on this trip, you'll just feel ridiculous trying to step ashore.

A Good Sweater

This is a wool sweater that my mother in law knit a while ago. I always wear it for outdoorsy stuff because it is pure wool, really warm, and still breathes. Great to throw on when the clouds come or under the waterproof stuff when it is really cold. 

A Sturdy Tote

You'll be schlepping loads of stuff to and fro, from food to linens to groceries. These L.L. Bean totes are perfect. This is the extra large one, and it fits just about all of the stuff we need for a weekend. These last forever too, and they look nice.

Classic, Relaxed Clothes

They have clean lines, they're easy to pack, and you will always have something appropriate. I leave all my frou-frou at home on a trip like this. No Strange Funky Shirt, no studded platform heels. The hair straightener should stay home, as should most of your beauty products. Minimal makeup, sunscreen, and a few classic pieces that fit well are all you need. Choose wisely. 


  1. Love all of this on you, especially the Chuck's. I'm beginning to think you couldn't look schlumpy if you tried. Bonus points for working in a Caddyshack reference!
    I swim like a rock so I tend to stay off of boats!


  2. Great post and photos, Kristin.
    I do have a sailing licence, however I don't only get sick on boats but also I get scared when there is a nice breeze which every sailor is looking for, so I don't find it an ideal sport for me *g*

    Annette | Lady of Style

  3. You look cool as fuck in your sailing attire. Cool. As. Fuck. Pardon moi my French!

    1. That's the best thing I've heard all week! Thanks Bella!


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