Real People: Wearing Tailored Clothes Casually

I find that many men like the look of tailored jackets, but are afraid of looking too formal. That’s understandable when, as my friend Christian once put it, tucking a pineapple-print shirt into some faded khakis can be enough to make some men overdressed these days. 

Philipp from Moscow, pictured above, shows how you can wear tailored clothes casually. The bolder glen plaid pattern on his sport coat helps distinguish it as a causal piece, and it’s been dressed down further with some khaki chinos. The light blue shirt is also less formal than your office-standard of white, and here, it’s worn open collared and without a tie. The tie-less look will rankle many traditionalists, but I think it’s a smart move if you live in a casual town. To finish the look, a silk handkerchief from Rubinacci adorns the breast pocket. 

As I’ve said before, if your clothes fit you well, you can dress quite simply. There are no frills here, and the color palette is quite sedate. This is about as simple as you can get, but it looks great because the jacket’s proportions are classic (albeit with slightly wider lapels), and the fit is slim, but not skinny. Philipp has the good fortune of having his clothes custom made for him (the jacket was made by Raffaele Iorio, a tailor in Naples, from wool Philipp bought in Florence), but if you train your eye, you can find well-fitting garments as well off-the-rack. It just takes time.