Let's talk about the Rockport Men's Taylor Waterproof Wingtip Oxford. First off, the waterproof feature is legit. I wore these in light rain, and my feet stayed dry thanks to the Hydro Shield Technology. No soggy socks here!

The genuine leather upper is a win—it looks sharp and feels durable. Over time, it’s only gotten better with a nice patina. Cleaning is a breeze, just a quick wipe and they’re good as new.

Comfort? These shoes are like walking on clouds—almost. The flexibility is great for all-day wear, whether you’re running errands or stuck in back-to-back meetings. But here’s the catch: the cushioning could be better. My last pair (not Rockport) had plusher insoles, so that was a bit of a letdown.

Fit-wise, Rockport nails it with extended sizes and widths. As someone with smaller feet (6.5), finding stylish shoes is a nightmare, but these fit perfectly. However, one reviewer got a pair that was clearly used—yikes! Always check for that ‘second life’ sticker.

The arch support is solid, but if you need extra cushion or a pointier toe, this might not be your holy grail. Overall? A reliable, comfortable shoe with minor quirks.