Men who care about presenting themselves well almost universally care about shoes. Well-made shoes last longer, look better, and are usually more comfortable as they break in than their lesser counterparts. But I'm at the beach and I'm not going to talk about shoes today.
A controversial footwear item that gets discussed this time of year is the sandal. The reigning cry of snobs is severely anti-foot, and strikes me as a bit self-loathing; we all have feet, so why the surprise at their sight? As bipeds, we should be proud of our evolved method of locomotion.
A personal favorite is the Rainbow sandal. They have a simple, un-embellished design and, while they might not be appropriate for the office, there isn't a better beach staple in my opinion. I've had probably 6 pairs starting in early high school and have loved every one. The breaking in process is a little bland. They feel lifeless (especially if transitioning from a old, well loved pair) and can get a bit abrasive; but compared to breaking in a new pair of Aldens, the process is relatively benign. Over time they mold to your foot in a way that feels like you may have been born with them. These are the glory days and should be embraced as such.
Because just as illusively as they became perfect, they will start to decline. The first crack in the leather is the beginning of the end. And eventually, someone in your life will toss them out (usually behind your back), forcing your hand to buy a new pair. And again it begins, like tides in the marsh...