I don't wear them as much as I used to, but I have two pairs of Sebago Docksides in Navy and Dark Brown. The OP's second picture is a classic model. They look fine with chinos, denim, and chino shorts. Very traditional American footwear for the summer. For casual slip-ons, I prefer burgundy penny loafers or tan horsebit loafers.
I have several pairs of topsiders but don't wear em nearly as often as I used to. Still essential tho.
This is what I'm wearing currently. I find it a tad less douchy, and meaningfully more comfortable than the classic "boat shoe", but serves a very similar purpose. I'm fine with "boat shoes", too. Slip-on is awesome. Comfortable is great. Classic look is nice. I probably wouldn't do the multi-colored stuff though.
I think boat shoes of the more traditional build and colors (tan, darker brown) are pretty much an essential for a young male today, but I'm really not a fan of the boat shoe/sneaker hybrid similar to the shoe pictured above. I get that they're trying to make it more comfortable, but sometimes you gotta sacrifice a tiny bit of comfort to look good.
I used to wear those things all the time, pair after pair years ago. Then not at all, ever since. NOt sure what happened. No specific reason, just moved on for some reason. Nice memories of removing them, indoors, around people.
I don't have a yacht, and I do not wear those shoes. They look like you're trying too hard. For work I wear black Ferragamo's, unless I'm having to interact with a bunch of low level staff, in which case I'll wear Johnston & Murphy to try to fit in better. For casual I have some brown Ferragamo slip ons that I wear On boats I'm wearing flip flops, and to workout cross trainers. Those are my shoes.
I prefer these, with the Vibram sole. Probably my favorite shoes-- wear them all the time. Spoiler Or these. Spoiler