Um, can you please explain this one? Loafers and jeans... and a winter coat. What's the problem?Glad you asked. First, the shoes. This is more or less what the loafers he was wearing looked like (image borrowed from the Allen Edmonds website):
This is not a shoe I would wear, but that's fine; I know people who wear shoes like this. My first issue with these is that they are very dressy loafers. They're kind of European, and tend to go with much more dressed-up casual outfits. They aren't really meant to be worn with a suit, but sometimes people do, and if you have enough personal style to begin with, you can occasionally get away with crossing that sort of line, depending on the situation. These shoes in tan, with a summer suit and no tie, on the right person, in the right setting, would work.
The guy I saw in the T station wasn't wearing anything else dressy, which was my first problem. Wool dress pants or trim-fit pressed khakis in a darker color would be all right. Jeans are iffy. The guy's jeans were a darker blue, but they weren't the sort of really dark denim that can sometimes be dressed up. They were just jeans, and they were boot-cut, which was my next problem. The wider leg of a boot-cut jean is just too casual to wear with shoes like these, regardless of the jean's color.
On top of everything was the jacket. I tend to pick on North Face jackets because I hate clothing with logos, but also because every other person I see on the streets and subways in the winter is wearing one. It's the lowest-common-denominator winter outerwear for people who don't care about clothes and just want to be warm, or people who want to project an image of being outdoorsy. And no one has any business wearing dressy shoes with such a jacket.
People who care about style always say details matter, and it's absolutely true. What people sometimes tend to forget or overlook is that the details matter both on their own, and in the context of the entirety of what you are wearing. You have to think about how everything is going to look when combined into an outfit. That's why this guy caught my eye, and that's what really bothered me about his outfit.
There are several outerwear choices that would have looked fine with these shoes, and might have allowed me to overlook the jeans: a peacoat; a traditional wool overcoat, in knee or 3/4 length; a trench coat; a hip-length leather coat; even a Barbour, which is borderline but I think could have worked if it was navy or black. Most of those lean toward the dressier side of the outerwear spectrum, and that's the key. You can't combine something dressy (in this case, the shoes) with something as overtly casual, technical, or sporting as a fleece or soft shell, regardless of what brand it is.
You want to wear your North Face? Fine, wear your hiking shoes with it. You want to wear those fancy bit loafers? Fine, get a nicer coat. You want to wear boot-cut jeans? Fine, get some boots. Details matter.