While it's true that I may have an unreasonable disdain for rubber overshoes of any kind, in wet weather some things are absolutely indispensable. Chief among them is a good quality umbrella (or two).
To begin with, if any man is going to have only one umbrella, it should be a long black one with a cane style handle, preferably with a wooden handle and shaft. There is simply no better choice when wearing a suit and long raincoat, or even formal wear, but it will do the job just as well with any attire. This is one thing worth investing in new if no other option is available to you, as a good one will likely be the only one you'll ever need. Besides, if you fork over significant scratch for it, you'll be that much less likely to leave it in the back of a taxi. I've had mine for many years, and the previous owner used it for many years. Whatever you do, though, please don't walk with it like it is a cane, unless you want someone to take it from you and beat you with it. Mine was of course procured second hand, but good sources for new ones are the usual men's shops (Brooks, J.Press, etc.) or places like British makers like Swain Adeney Brigg if you're really feeling flush.
A smaller umbrella that will fit easily into a bag just in case it's needed is also a handy thing to have. Mine is one of the old duck head kind, with a wooden handle and metal shaft. I used to see these everywhere when I was a kid, in every color. They were something of a New England staple. They're perfect with casual clothes, and especially with "preppy" stuff like navy blazers and khakis, though they can be admittedly a tad precious if you don't happen to live in Boston. Whatever kind you buy, be sure it's a good one, and not a cheap piece of junk form the drug store. A good one will work better, and again, if you actually pay for it you might not lose it.
As for footwear, in my previous post on the subject I suggested low cut Bean boots. But in a light rain, there are other options, besides those ghastly rubbers things:
mentioned this before, too. This pair of bluchers was recently acquired at a thrift shop for $5.49.
my other pair on the ten minute walk from my house to my job, and I've never had any problems. On arrival, simply wipe clean with a paper towel.
p.s. new items just arrived in the Shop, see here. In other shop news, I've recently cleaned up the "new" button so that clicking on it sends you items that are actually, you know, new. I've also added a link direct to the Brooks Brothers offerings in the side bar here, along with Polo, for customers interested in those two brands particularly. I do find a lot of that stuff.
p.p.s I've added a new page at the top, "Reader Finds". If you've found a great piece at a thrift shop, feel free to share it here. Email me with photos and info, use "Reader Finds" in the subject line.
p.p.p.s. in spell checking this post, I spelled "duckhead" as one owrd, and the spell check suggested "dickhead" as a replacement. Wow. Pardon my French, please.