Perspectives of a Lady, Gentleman & Dane

sailing Archive

Hannah Sheflyand

We got our certification over the weekend! Now we just need to find some sailing buddies so we can get the opportunity to go out on the water more. We spent Sunday evening looking and admiring the different style and size sail boats and watching different videos of these boats out on the water.

I learned Brian and I have very different expectations for what we want when it comes to the ideal sailing day out on the water. Brian wants the experience of strong wind in his face, water hiting the deck and the thrill of the boat heeling over (turning to its side). He loved watching the racing videos (example above) and wants to go that extreme!

Team Tilt D35 LvS

Yikes, Im happy I have a strong stomach to handle it all.

I, on the other hand, imagine the perfect day out on a sailbout is to relax on the deck with a nice drink and the sun setting behind me.

This would be ideal for me...

This would be ideal for me…

Luckily we both enjoy each others company enough that we will probably compromise and spend our future sailing days indulging in both of our imagined perfect days out on a boat.

How about you? Whats your perfect relaxing day outdoors, near the water or up in the mountains? Or somewhere completely different?

Hannah Sheflyand

Yesterday was our first sailing class! It was definitely an overload on new terminology but I have no doubt that some prep work and studying will do the trick. This weekend we will get to spend time out on the water on a 24ft sailboat and then hopefully be certified to sail on our own by Sunday evening.

The first thing we learned in class is that our wardrobes need a little boost when it comes to sailing. This week Brian and I will be on the lookout for a good amount of items we need before we hit sail.

Regulars shoes or going barefoot is really not preferable. Deck shoes have razor cut soles, which are special slits that open as the foot flexes and allows the shoe to grip on a wet deck, and keeps you from busting your ass. Most shoes also have dark soles that can mark the deck which is a no-no. I thought it would be pretty easy to find but I think both Brian and I are pickier then we thought.

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Henri Lloyd shoes look great and they have sizes for both men and women. These Valencia Leather shoes are my favorite and are highly rated.


Another great variety that steps away from the typical deck shoe look is the Octoskins. I like them because they are a little more feminine then the shoes I was considering before.

Both Brian and I wear glasses and see pretty poorly without them but on the boat there is a fear of having them fall off, so as dorky as they look, we will both be wearing glass keepers on all our future sails.


Chums makes a very simple and cheap glasses keeper and it comes in a variety of colors which I think is a perk to such a goofy look.


I think Brian will prefer a pair of Croakies since they look a little more macho. Which do you think will look better on us?

Most of your time on the sailboat is spent looking up at the sails which also means looking up into the sun. Hats unfortunately are not flattering on me or Brian, but it is a must when you are out on the water.


I don’t think Brian will agree to wearing a visor, but I love the Gil Visor, especially with the little cord to hold the glasses keeper.

And last but not least are sailing gloves. The sailing classes list these as optional, but with my little frail hands I am not even considering going without them. Brian thinks the opposite of me regarding the gloves and is going to go without them for the first weekend and just see how he feels.


There are companies that offer more feminine version with pink or purple, but every sailing blog out there has mentioned how amazing the Gil Deckhand Gloves are and I will be picking the perfect fit later today.

I feel once we have these items figured out, and I pick the outfit and the shoes (or these shoes), we will be ready to go.

We are both very excited and cant wait to share our adventures, as long as we pass :)!!!

Hannah Sheflyand

I love summer, not only for the warm weather, but because everyone brings out their A game when it comes to style. It is also when my wallet is the least happiest because I am trying to catch up on the new styles and I overfill my wardrobe. I come to the blog world hoping that you can help me make a decision on the next pair of shoes I should keep.

These are all Sperry Boat Shoes, super comfortable and cute. I wish I could keep them all but unfortunately I can only pick one. What do you think? Which do you like the most?

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Hannah Sheflyand

I am getting more and more excited as our sailing classes are coming up. I want to have the perfect outfit for the first day out on the water, and since I have the shoes covered, now I just have to worry about comfortable clothing.

Some of my ideas for outfits:


I like the classic, comfortable look of this outfit – Wrinkle Resistant Shirt $50, Stretch Pants $50



It would be great to wear a skort but then it might get chilly, the hoodie would be more comfortable but the cardigan is so cute- Hoodie $55, Skort $45 & Coveside Cardigan $65.



A sporty outfit with an awesome pop of color, Short sleeve crew neck $30, Slim leg capri $55

What do you think of the outfits? Which should I wear the first day out?

Hannah Sheflyand

Brian and I signed up for sailing classes! I apologize in advance, as the classes get closer I will end up posting a lot as my excitement grows.

As everyone is starting to wear more summer clothes I am in the mood to buy some classic style summer shoes (not sandals), especially since right now I cant wear shoes at all. With my new admiration with sailing these are the few pairs I have been contemplating on buying. What do you think? What are your favorite shoes/sandals to wear during the warm summer months?


Top image of Arthur Ravenel Bridge in Charleston by Etsy shop OurFamilyPhoto