Old School Cool

Some more old school jean pictures. The men in these pictures wear their clothes well. There is a nonchalance to the clothes that they wear and how they wear them. Style & Fashion comes off as an after thought, yet they are all immersed in it. But the utilitarian aspect of their clothes is very clear. Also, as we have discussed before, the jeans are all slim and well tailored.

Steve McQueen in the top photo, no one has ever pulled off a white shirt and jeans better. But notice he doesn't go with the typical black boots, but instead comfortable understated shoes. I can imagine them being brown suede boots, similar to these suede McAllister boots at JCrew. It makes the outfit more natural and less try-hard. A white shirt and jeans can easily come off as try-hard, because it is such a simple outfit.

The two men below have great natural style. The Cable knit sweater over the polo shirt on the man on the left is naturally cool. A classic style that will never go out of fashion. The man on the right has a great jacket over a button-down shirt. Both have jeans tucked into calf height boots, due to the mud more than the style. That is how that look can be done best, when it is necessary to keep the jeans out of the mud or rain puddles. Otherwise, it looks to planned, but when it has a purpose it looks natural, necessary and very fashionable.

In the final photo, the man on the car has great style. He has the cuffed jeans and loafers, a great and classic look. This look is best modernized with either colored socks to match the shirt or no socks at all. Also, I prefer loafers with no tassles. He has a herringbone or tweed jacket which is great way to dress up the jeans. The collar on the jacket is popped, not out of style, but out of necessity, since he is waiting outside on his car hood for his date. Once again, the utilitarian need for the popped collar gives the fashion purpose and makes it look very natural. A popped collar for no reason looks out of place and planned.

Fashion is best when it looks natural, fits the surroundings, is purposeful, appropriate and shows no signs of long-term planning. Style comes from the un-planned, subtle details that make it look sprezzatura rather than forced. Focus on making the little touches look spontaneous, even if there is extensive planning behind them. Think old school cool and your style will come through in the details.