They actually hold up because the construction is solid - not flimsy retro pastiche. The sole doesn't collapse after a month, the stitching stays intact, and yeah, the leather does soften without falling apart. That matters when you're on your feet all day.
The sizing thing people mention is real though. Size up half a size, maybe even a full size if you've got wider feet, or you'll spend weeks fighting with them. Once that's sorted out, most people find they settle in pretty quick and stay comfortable. They're not like those stiff vintage reissues that feel like punishment - the Sambas have enough give in the materials that they work with your foot instead of against it.
Whether they'll still be cool in five years is honestly a different question, but comfort-wise they're legit. People aren't wearing them ironically at this point - they stick around because they actually function. If your workplace bunch switched over, they probably already figured out the sizing and broke theirs in, so that's worth asking about.