Urban walkers: what do you wear on your feet for rainy conditions when you will be doing a LOT of walking?

I’m asking this question because there have been quite a few comments on my ‘packing for UK’ thread that I consider footwear for wet conditions - and that the Converse sneakers I was planning to wear might not keep my feet dry.


At home I wear sneakers for long walks in all conditions, except snowy winter days when I wear combat style leather boots. It has been a mild winter, so I have worn the sneakers when streets and sidewalks have been clear, and the boots when it has been snowy, or icy underfoot. My tall boots, and shorter Chelsea style are not great all day footwear. I was thinking of adding a second pair of combat boots in a colour or pattern - next winter. Maybe I should look now and break them in for May?

If you were packing footwear for a 2 week urban vacation in May, what 3 pair would go into your suitcase/on your feet?