Mine were pretty comfortable from the start - that's one of the main reasons why I bought them.

For reference, I have the Ohana's which are rubbery. I can't speak to their leather ones which might be different.

For comparison though, I had the rainbow sandals with the leather bottoms and those definitely felt very woody, and even after a year I didn't feel like they got any better. Maybe with more time they would have improved but the sole started to split about a year in, so I never got to find out.

I bought a pair of the flip flops while in Hawaii despite being told by the sales rep they were the “Cadillac” of flip flops (fwiw we have had terrible experiences with Cadillac but that was in the 80s).

I was a bit wear about spending $60+ on flip flops especially after having spend about the same on Rainbows which started to fall apart after about a year.

It’s been several years since I bough the Olu Kai’s and I wear them very frequently during most of the year. Granted, I’m not doing anything hardcore in them but they do get a lot of mileage. After all this time they have held up surprisingly well - almost no noticeable wear and tear.

For me, the biggest upside is the overall comfort. Compared to most other flip flops they offer a lot better arch support and don’t require any kind of break in like Reefs or Rainbows. The durability is really just a bonus at this point.

If/when these wear out I definitely plan on buying another pair to replace them.

Lady White tees. They’re a bit pricey, but they’re made in Los Angeles from cotton sourced from NC farms. I’ve bought a few of the 2 packs to make the price a bit more palatable.

The hand feel is crisp and you can tell the quality of the fabric. They’re a little stiff at first, but break in really nicely and feel even better at the end of the day than when you first put it on. Really high quality stuff.

Another point is the stitching on these is next level. I’m not really one for details on things like a tee shirt but once someone mentioned it to me I couldn’t stop noticing the little details that set these shirts apart from most of the mass market stuff.