If you look around the tea shops of London, you will notice one thing. Although it is likely raining out, there are dozens of well-dressed men inside who are dry as tea-biscuits. Here are some rules for staying stylish in the wet spring weather.
Rule #1: Get an umbrella.
But it has to be the right one, because the right umbrella will look stunning in your hand. I know it’s inconvenient. But so is rain. So keep one at work, and one by the door of your apartment. Perhaps a third umbrella belongs in the car.
Please, in the name of dignity, avoid the collapsible type — you’re not Inspector Gadget. Your umbrella should also be tall enough to reach your waist. That way it will be long enough to cover your head from a comfortable, rested position (reference Davinci’s "Vitruvian Man" for a diagram of armspan/leg hypotenuse).
Unless you are in a pinch, never buy those ridiculous two-foot handle umbrellas on the street (unless you’re a circus bear with a unicycle).
Barney’s of New York makes a few models that you will never forget at the restaurant.
Also, a quick word about umbrelladom: the proper umbrella will protect you and your clothing from the dampness. A soaked jacket will never fit right again, and if salt water gets into your shoe threads, you will always have trouble polishing them in the future.
The proper umbrella is the ultimate gentleman’s accessory, because if you run into a friend who is standing like a lost cat, shivering under an awning, you can say, "Come under here before you catch your death."
That said, it is never acceptable to walk down the streets of any city with a golf umbrella. You will poke people in the head and take up too much room, forcing older men to step into the rainwashed gutters and ruin their shoes. The only appropriate time to use a golf umbrella is when you are out on the course, tempting Thor.
Rule #2: Waterproof shoes.
When I was a child, my father was a pavement-pounding consultant for Arthur Anderson. The company handbook specified that all consultants had to arrive to client meetings in a three-piece suit with a full-sized umbrella, rain or shine. You were not permitted to sully the image of Arthur Anderson by dripping in meetings until the firm evaporated (that was Enron’s job.)
My father also wore what were then called "rubbers." These are thin black raincoats for dress shoes. Don’t be embarrassed by the name. You can take them off in the vestibule and walk into any room on a rainy day looking like you just had a shoeshine and a brisk walk. If you’re worried about what to do with these dripping prophylactics once you arrive at your destination, you can always hide them inside your umbrella and bind the strap. Just don’t forget to bind the strap, or you will look like you were trying to perform something comic.
If you think you can get away with it – even just for travel – get a pair of Sperry Topsiders (link here). These were designed in 1935 by an avid boater who one day realized that he tended to slip on the wet deck while his dog simply trotted along steadily. The shoes have a herringbone pattern in a white-rubber sole, which means they are also non-marking on boat decks and marble floors. They also have reinforced stitching that makes them waterproof and comfortable,without making you look like a camp counselor.
If you’re just looking to keep your nice shoes dry while you step out for lunch, you can take your socks off and wear your Sperry’s barefoot (not recommended for other shoes). That way you can walk around looking like you’re on your way back to the Yacht.
Rule #3: When you get to your destination always look for the umbrella bucket.
Your umbrella does not belong in your bag. It’s not a pair of gloves. It’s a raincoat that doesn’t smudge your profile. Leave it at the door so you don’t drip all over the floor and make someone’s grandmother break her hip.
When you put it down, repeat to yourself, "I will not forget my umbrella, I will not forget my umbrella…"
And you won’t. Because remembering your umbrella reminds the world that you currently have your life in order.