Not every personality is going to pack and carry that kind of stuff. We carry less each trip. Great eye-wear would get much more use from some sailors.

http://www.kaenon.com/lens-tint/

Once you get the new fabrics correct for you. You will never want cotton on a boat again.

TECHNICAL QUICK DRY SAILING SHIRTS

http://www.apsltd.com/sailing-clothing-apparel/sailing-shirts-rash-guards/technical-shirts.html

Every sailor should have at least one head to toe set of tropical weight technical apparel in a style they are willing to wear. Who likes wet clothes?

Every person who carries a knife should also have cord on their person 24/7.

https://www.survivalstraps.com/

Parachute cord can be very inexpensive. I always have some at the bottom of every bag.

The airlines make the new very personal PFD's a challenge. We should all have PFD's on every time we exit the cockpit.

Warning! With the FAA rules this one gets complicated!

https://www.mauripro.com/us/category/1-Life-Jackets-Inflatables.html

Once you rescue someone who has been in the water for any length of time you will become a believer in the PFD always on practice.

The win is? Will he pack it? Will he actually use the gift?