The latest issue of Details magazine has, in one spread, a guy wearing what appears to be a muted grey, brown, and light blue Prince of Wales sports jacket, a blue and white striped shirt with a contrasting white collar, a dark blue dotted tie, and a blue and white pocket square. He is also wearing a tie pin. Everything is a reasonable fit, although sticklers may say that he is not showing enough linen at the cuffs, and it is a very nice job of pattern matching (most guys would get it completely wrong, but hey, stylists at Details are paid for this type of thing). Then you check out his pants, and that’s wear it all goes wrong. He is wearing some slim fitting, faded jeans. It looks like he forgot his pants at home.
I had a uniform in high school. Shirt, tie, sweater, grey flannel pants. Occasionally, I’d forget to bring pants to school, and I’d try to get by with jeans. Not a single teacher fell for that. Even though they had the combined style of MC Hammer (this was back in the 80′s), they knew that the kid with the jeans looked like crap. Now, to be fair, thee jeans shown in the Details article fit the model a lot better than the Orange Tab Levis I wore, but still, the net effect is the same: “Dude forgot to bring his pants.”
The problem with the look is that there is nothing on the top half that suggests that he might wear jeans on the bottom. The shirt is not slightly wrinkled, nor is the collar a soft one. The sports coat is not made of a more casual fabric like hopsack or twill. Now, I know that Hedi Slimane is often photographed wearing a black jacket, white shirt, and dark jeans, but he never wears a pocket square, and his tie is always slim and seems put on as an afterthought, tied loose around his neck. Tom Ford (and unless you are Tom Ford, I would advise against dressing like Tom Ford) wears a white shirt, black sports jacket, and jeans, but the shirt is often unbuttoned down to his navel. Where it works is when the formal element stands alone, looks thrown on nearly as an afterthought, when the jacket is unmistakably casual, in either the cut, or the fabric, or both, or when there are other casual elements on the top matching the jeans. These might be a soft collar, unbuttoned shirt, a tee, a v-neck over, or instead of, a collared shirt. Possibilities are numerous.
And please, for the love of all that is good and holy, do not bottom out with a pair of chunky black, rubber bottomed shoes that are an evil mess of sneaker and shoe, and not properly either. The all black Prada Sport shoes are the worst. Not only do you look like a refugee from 1995, but it looks like you want to have it all ways, which, everyone knows, can’t be done. So either go with classic sneakers, or with a good solid boot.
The sports jacket with jeans thing can definitely be done. But most guys still end up looking like those East German businessmen I used to see waiting for the train from some place to Berlin or Frankfurt, with boxy jackets, tight jeans – often stonewashed, black, or both – and the ugliest shoes this side of Aldo. You don’t want to be that guy, do you?