What To Wear During a Sail

Immediately after signing up for my first Club Sail, I had this instant realization that I had signed up for something that I may not be prepared for, and I had no idea how much it would cost to get prepared if I wasn’t. For some reason, it never crossed my mind that I may need special sailing stuff to go sailing.

Fortunately after a moment of stressing over a decision I was beginning to think I made quite impulsively, I found an email in my inbox regarding my Club Sail registration. In it was a short but useful list of recommended items to bring:

  • Sunglasses and a hat
  • Sailing Gloves (bicycle gloves without finger tips will work)
  • Sunscreen
  • Boat shoes, light or non-marking soles only
  • Multiple layers of outdoor clothing
  • Foul weather gear if rain is in the forecast
  • Lunch and Beverages

Others may have a different reaction to this list, but my very first reaction upon reading it was, “What are boat shoes?” Fortunately, my roommate’s sister is an experienced sailor herself, and so I figured he would know so I asked him.

He grinned and laughed when I asked. “They’re like rich boy loafers,” he said.

Rich boy loafers?! Honestly that was not what I expected to hear. A feeling of dread came over me. Was I really about to embark on this new hobby, an activity that is expensive by nature already, that I would need to maintain a certain class of fashion that I had not expected? I certainly hoped not, and going into this purely as a beginner, my goal was to spend the least amount necessary on this initial investment.

I quickly did Amazon and Google searches for “boat shoes” and “sailing shoes,” and sure enough loafer type shoes returned as the result. But the price range was broad, and I quickly learned I wouldn’t have to enter the world of high-end boating fashion, at least not immediately.

For my initial set of boating wear, I was able to keep things fairly cheap, and some items I purchased I have been able to use on a more daily basis. Below I will document the items I bought with pictures and my personal thoughts and notes about them.

Boating Shoes

The shoes I chose is a pair of Bruno Marc New York shoes, specifically the “Men’s Pitts Penny Loafers Moccasins Boat Shoes” as titled by Amazon (expect for one item, everything came from Amazon). You can find them on Amazon here: https://www.amazon.com/gp/product/B0785T7TZ3

First of all, they were only $25 bucks, so if I hated them, it wouldn’t have been that big of a waste. However, I think they’re really cute shoes, and I really love them. My feet feel very comfortable inside of them, and I have been wearing them several times a week. I even find them appropriate for work when I can keep a more casual appearance. Overall, I’m very happy, and I think I’ll check out more of the Bruno Marc New York brand.

Sailing Gloves

These are the the MRX Boxing & Fitness Gloves which Amazon describes as “Multicolored Sailing Gloves with Sticky Palm Grip for Men and Women, Short Finger or 2 Cut Finger Gloves for Fishing, Yachting, Workouts.” They cost me $15 bucks, and for the most part, it served its purpose.

During the sail itself, I had to pull on and keep control of line/rope, and the sticky palms worked great for that. My only complaint is that my hands got very cold (this was a December sail in the San Francisco Bay), but not having any experience with any other gloves, I don’t know if different gloves would have kept my hands warmer or not. You can find them here: https://www.amazon.com/gp/product/B01KI0YD6S

While searching for the amazon link for this post, I noticed that this pair of gloves is available with the thumb and index fingers cut, and the middle through pinky fingers covered. During my sail, the other guys’ gloves were cut in this way, and if I could go back and redo this purchase, I would have bought that cut instead.

Moisture Wicking Thermal

Believe it or not, “wicking” was not a term I was familiar with until recently. My roommates kept saying I need to find “wicking” clothes for sailing. “Water-resistant” or “water-proof” is what I would normally describe such clothes as. Now I see the word everywhere, and I really can’t believe I haven’t noticed clothes described as such until now.

The above thermal is the Dickies Men’s Long Sleeve Heavy Weight Performance Flex Thermal Tee. At a mere $15 bucks, I really liked it. It fit well, and I felt comfortable in it. Coupled with the jacket I wore, my body felt warm throughout the entire sail. I wore this thermal under a moisture wicking athletic shirt, which looked nice and kept me dry. You can find the thermal here: https://www.amazon.com/Dickies-Performance-Thermal-Heather-X-Large/dp/B07HFGMCLD/

Waterproof Pants

These pants are the Portwest S441 Rainwear Men’s Waterproof Rain Pants. They’re not very special at all, and they definitely have that plasticky, rain proof feel to them. But at $12, I thought it was a good investment in keeping myself dry, on a boat, in December.

On the day of the sail, the forecast for rain was replaced by overcast and fog, and so I left the pants at home. My plan, however, was to wear them over my jeans should rain have been in the forecast. I had tested them over my jeans at home, so I know they are large enough to wear over any other normal bottom-wear. With that, I was not able to test out it’s all-day-wear comfortability and its rainproof capabilities. It does appear to have the non-breathable, plastic, water-proof feel so I’m sure it would have done a great job at it’s one purpose–keeping me dry! You can find these pants here: https://www.amazon.com/gp/product/B007IS0W9G


I had actually bought two jackets. The first one I bought as a way to keep things cheap, and then realized, this was not a purchase that I can be cheap with, especially in December. So my priciest purchase was the jacket, and the day before the sail, I trekked over to Kohl’s and searched for a jacket to protect me from the cold, December, bay air. Let’s begin with the jacket I did wear first:

This is the Men’s Hi-Tec Scotch Bonnet Jacket, and I love it. I love all $99 worth of it! It was comfortable. I felt warm and cozy inside of it, and I felt confident it would keep me dry. I really needed to add an all-weather outdoor jacket to my wardrobe anyway for any winter extracurriculars (outside of sailing) that I may participate in.

When I found it at Kohl’s, it had a tag on it that said it was “water-proof,” so that was an important selling point. The tag said other things on it that I remember impressing me, but I can’t remember everything the tag listed. I was able to find the jacket on the Kohl’s website, and it had this listed as “product features,” which I believe some, if not all, features were listed on the tag:

  • Heavy weight design
  • Waterproof Construction
  • Hi-Tec Thermo fabric traps in heat to provide warmth
  • Zip front
  • Long sleeves
  • 4-pocket

I must admit that there was never a point during the sail that I ever got wet, not even a light spraying of water. Let’s consider this a testament to the skills of our Skipper who led 2 experienced beginners and 1 total newbie through a safe fun day on the water. With that, I can’t say that the Jacket kept me dry. It is, however, 100% Polyester so I imagine it would have done the job.

This jacket is what I originally purchased on Amazon for $25 bucks. It’s titled the “Baleaf Unisex Rain Jacket Packable Outdoor Waterproof Hooded Pullover Raincoat Poncho.” It actually folds into itself into one of the pockets for easy storing. Like the pants, it has a non-breathable, plasticky, rain-proof feel to it, but it’s very light, and I’m pretty sure it wouldn’t be great at keeping me warm. It’s just not made for that.

Unfortunately, I have no idea what i would use this jacket for. Maybe I’ll find spring and fall outdoor activities to wear it during, but I generally don’t find myself in situations where I need what is essentially an athletic rain jacket. Since it folds into itself, it might be worth keeping in my backpack as preparation for any inclement weather I may unexpectedly face. You can find the jacket here: https://www.amazon.com/gp/product/B07HGX6YRP/

Other Items and Thoughts

As stated earlier, I had worn a moisture wicking athletic t-shirt that I had already owned. I wore that over the thermal, and that worked out really well.

One item I wish I had during the sail was some sort of moisture wicking beanie. My ears got very cold and I really wanted to cover them. Unfortunately, due to the wind, it was difficult for me to keep my jacket hood over my head, and the times I was able to keep the hood on, my view was restricted when trying to turn my head, and I wanted to look at everything. I’ll be sure to buy a beanie before I get on the water the next time!

Other than needing a beanie, and prefering 2-finger cut gloves, I think I made some decent purchases to prepare for learning to sail. I also really love the shoes and jacket I bought, and I plan to get lots of non-sailing use out of those items as well. I spent close to $200 for these items, and although it was more than I expected to spend (I originally hoped to do this for less than $100), I feel comfortable taking on sailing during these cold months.

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