When I lived in Boston and spent more time walking than driving, rain boots were a must. It rains a lot in Boston, but no one will ever tell you that.
Denver was much more dry so I gave my rain boots to charity.
When I recently moved to Chicago, right when the city and surrounding suburbs were finally thawing after a very long winter with record snow, I realized I needed a pair of rain/rubber boots once again. Every time I walk the dog I ruin another pair of shoes after accidentally sinking one or both feet in a mud pit. The snow has also been replaced by rain (which I never thought I would welcome again but I do not want to see another snowflake until I am skiing in the mountains).
So, I decided that it was time to again invest in a pair of Hunter boots. I decided on the Shoreditch Moto Boots because they have a bit of an edge.