Over the years, I've had a few pair like the ones you see above, and I really tried to use them. I've also owned sock garters in the past, and tried to like those, too. In the end, I find both things to be just plain silly in the modern world, the exclusive province of guys who do old stuff just to do old stuff.
And don't even get me started on Swims, their overpriced and somehow fashionable off-shoots.The only thing sillier than rubber overshoes is overpriced pseudo-fashionable "cool" rubber overshoes.
So what, then, is a fellow to do? The answers vary. For many men, it's easy to simply take refuge in the fact that pyjamas now suffice as clothing practically everywhere these days and cover up in some high tech waterproof camping stuff. Or you could just stay inside.
Fortunately for me, I live in New England, near Boston, in the epicenter of that uniquely American style of dressing up with extreme elements of casual leisure thrown in, of combining proper dress with sensible dress in just the right way. Fortunately for the rest of you, this way of dressing not only happens to be enjoying a moment of fashion right now but is also far more generally acceptable in more places than ever.
To begin with, these are the shoes that will keep your feet dry. Bean Boots, Original Maine Hunting Shoes, Duck Boots, whatever you want to call them. In Winter I wear a high cut pair with woolen socks. On the second day of June, I wear slip on moccasins with cotton socks and cheap khakis.At work, I keep an old pair of penny loafers to change into. There is one and only one source for these shoes : L.L.Bean. Don't bother with any others. But of course, you knew that already.
Up top, a Brooks Brothers shirt and blazer with an tie from the Andover Shop are all kept dry and clean under a Barbour jacket. Yes, in Boston you sometimes find yourself wearing a jacket over a jacket over a shirt and tie even in June.
The whole thing enters near abominable territory with the addition up top of a ball cap to keep the head dry. Truth be told, a ball cap atop jacket and tie is a time tested option in foul weather in Boston. Tread lightly here. Ball cap and suit is likely no good; ball cap and blazer with khakis is manageable. Red Sox hats and their derivatives are best. Country club and gold course caps work too, but only if you belong or play golf there.
The overall effect is a perfect fusion of correct and sensible, if a little laid back in its way. But that is the very heart of what this stuff is all about. Don't forget that above all the clothes should fit well, if even a little slouchy. Remember that when this "preppy fashion" moment passes and you should be able to wear this stuff for the rest of your life. Then your boy can wear this stuff for much of his life.
Oh, and your feet will stay dry.


