I live in a cold, rainy northern city where many people like to think of themselves as rugged outdoorsmen. Outerwear is usually items designed for hiking or athletic use- parkas and fleeces, often with hoods, which are good to have if it rains.
A parka- the brand is often North Face, which I think is mentioned in “Stuff White People Like”- tends to be bulky, for protection from the cold, and loose, for wearing over other layers and ease of movement. While functional, neither of these is attractive. A good question to ask about any item of clothing is, “Was this specifically designed for this use? Would it be more appropriate in another context?” Camping or athletic gear should only be worn when camping or doing something athletic.
You may have on a dress shirt, dress slacks and dress shoes, but put on a baggy parka and a knit cap or a baseball cap and you look like a schlub again. You should look good all the time, even outside in the cold. So what to wear for the cold and rain?
A nice overcoat or raincoat is the best bet. In “Dress For Success” John Molloy says a raincoat must be beige, but an overcoat can be black. He should be followed because unlike everybody else who bloviates on this subject he actually did scientific research. As a nerd you can dig that right? I’m confused on this one though because what about an overcoat that doubles as a raincoat, like London Fog? A nice London Fog with a zip out liner will cover you in most situations.
Another possibility is a pea coat, another thing mocked in SWPL but it looks a hell of a lot better than a parka. A car coat also might be good. I saw a Macy’s sale ad for Calvin Klein car coats for under $100. Don’t you think you will look better to that cute girl in a Calvin Klein car coat than a baggy parka?
What about your grape? The hood of a parka is always there, but you need something else. One, having the hood of a parka up makes you look like a refugee. Two, it cuts down your ability to see, and in dark rainy weather that can lead you to getting hit by a car. A high quality brimmed hat is a little impractical- some kind of a soft, water-resistant hat that you can shove in the pocket of your nice overcoat is more useful.