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I go through their leather shoes that are kind of like sandals and kind of like moccs, probably a pair a year, maybe two pair a year. I wouldn't put them in the BIFL category unless you just keep replacing them. I have a specific reason though, it's a persistent pain problem in my feet and these don't cause me any more pain so that's why I stick with them. Haven't found anything else to replace them with. The rain is tough on them so I try to keep it to wearing them when it's dry out.

I really like my rainbow flip flops. I wear them 4-5 times a week. I have had this pair 3 years, however then are on their last leg.

There are many different models that feel very different. They are best known for the synthetic ones (ohana). - which are very squishy and comfortable. Mine have proven reasonably durable.

I have a pair that just broke but I think the company offers repairs…anyone know?

Shoes aren't really BIFL in my opinion. They can be resoled and conditioned if they're leather, but they get worn out and need to be replaced if you want cushion between you and the ground.

Olukai is just kind of squishy. Rainbows are okay after the break-in period, but you have to have narrow-to-normal feet. Reef is my absolute favorite at this price point.

Try malefashionadvice!

I’m a socal native so I felt sort of duty bound to get rainbows. I actually had a pair just for walking around in my house because I hate slippers.

Anyways within 6 months, idk how but the leather foot bed cracked big time (maybe from just standard foot sweat?) and made them totally unwearable.

I don’t think I could ever buy rainbows or any leather sandals after that

I actually switched to olukai and love them. Had them about 6 months so can’t speak to their longevity

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.

I bought a pair a number of years ago. First day wearing them the soles of my feet turned black. Washed my feet several times, but it took days for the black to completely disappear.

No Olu Kais for me.

Yes, no.

I just bought my 3rd pair of Ohana’s this fall in at least a decade. They last way longer than everything else that looks decent. I used to get 6-9 months out of Rainbows. My Olukai Ohana’s last 2 years minimum. Skip Olukai’s leather models. They’re more fashion than reliability.

They do break in over time. I bought one pair of Reef sandals. Never again.

How did they feel when you first got them? They felt very hard and blocky to me. I've read that they're supposed to be really comfortable right out of the gate.

Yeah, I like the arch support but does the cushioning get better? I felt they were very hard and woody when I tried them.

Probably the model you selected. Ohana’s feel pretty good out of the box but I have low arches so eventually the arch support compresses and then they’re perfect. All shoes break in to some extent.

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've been wearing Olu Kais leather styles for about a decade now. For me, they have always broken in and felt much more comfortable after a few days to a week of wear. You might have to try on a few pairs in the same size to find one with a comfortable thong for you. I've noticed a very slight variance from pair to pair, probably from the nature of hand crafting. Some are tighter than others.

For me, the thong part of any flipflop is the part that fails. I have never had an issue with their soles. You can get them repaired through their website and I've had a good experience with that. I've only needed to use it once though.

The arch support is unmatched in terms of flipflop brands I've tried. The leather does break in really well. I've never had an issue with their leather dye staining my feet. My leather ones usually last me about 2-3 years of (almost) daily wear from about March to October. I usually get a new pair for daily wear and the older pair becomes garage/checking the mail shoes. I could probably wear them longer but they do start looking worn by the end of year 2 and not as nice for going out.

Compared to buying multiple pairs of cheapo plastic flipflops every year, I think they're worth the price and quality. Hope this helps!

Yeah, that's why I'm confused. I picked the ohana. Pretty sure I got the size right too. How would you describe how they feel to you?

I don’t know man. Seems like you’re in search of a unicorn. Lasting a long time and comfy out of the box are not traits that typically coincide.