The New Galosh
Galoshes have always been a somewhat inelegant solution to the problem of wet weather. Not only are you using two shoes to do the job of one, but most places you find yourself walking to won’t have an appropriate place to deposit your rain-soaked boots. In short, it may be simpler to invest in a pair of waterproof shoes handsome enough to wear to work.
These Tretorn versions are a favorite around these parts for just that. Modeled off a Chelsea boot, they should blend in with just about anything. Throw in an umbrella and some judiciously cuffed trousers and you should be just about impervious.