by David Isle

Learning to look good in tailored clothing can seem an intimidating task. Maybe you can identify some looks that you like, but you have no idea how that tie was chosen and you don’t even know where to get a windowpane suit, much less own one already. Meanwhile you dread looking just like everyone else in a navy suit or a navy blazer with grey worsted wool trousers (sometimes denigrated as “the security guard’s uniform”).

It doesn’t have to be this difficult. Some men delight in building large wardrobes of exotic items and puzzling their way through building an outfit every morning. But many other well-dressed men wear tasteful, well-fitting versions of classic outfits every day without ever boring themselves or their retinue.

Take, for example, “the security guard’s uniform” described above - a navy sport coat and grey worsted wool trousers. (Personally I prefer to call this one the “best dressed guy at a sports bar.”) The most uninspiring versions of this outfit include a nearly-black, oversized coat and uncreased wool trousers, a white shirt and black shoes (possibly even sneakers).

But the best versions, such as the outfit above from Richard from Boston, look great. It’s ostensibly unimaginative - it’s just a navy jacket and grey trousers - but the overall effect is distinctively natty. Why?

The first reason is that everything fits well - the shoulders and chest of the jacket (from Sartoria Formosa) fall nicely, the shirt collar has a nice spread, the tie with proportionate width and a full dimple but enough askew not to suggest fastidiousness. The second reason is the materials of the principal elements - the coat is a richer navy than your typical department store selection, and the pants are flannel rather than worsted wool, which gives more texture.

The third reason is that the other elements are chosen thoughtfully. The stripes on the shirt offer a welcome variation on the usual plain white shirt without being garish. The burnt orange tie is woefully rare for how well it accompanies a navy jacket. The pocket square complements the other choices and again distinguishes this outfit from the typical, but is not so conspicuous that I worry about the wearer running off to the men’s room to check the fold every 15 minutes.

With medium to dark brown shoes - suede for another elegant variation - this is an outfit you could wear dozens of times a year, with slight changes each time. Maybe a knit tie sometimes, a button-down shirt other times, and the occasional loafer. But nothing that keeps you staring at your closet in the morning, paralyzed by indecision. It doesn’t have to be difficult.