The combination of a plaid shirt and a tie is not exactly new, however the never ending styles that the combination can be executed is what resonates with me. A plaid shirt has always been casual and laid back for me, never did it occur that a plaid shirt can be dressed up, in both a casual and formal way. As long as the execution is right then a stylish appearance is guaranteed. I'm very much from the old school when it comes to men's style; I don't do the open collar, loose tie look. If a shirt collar is rigid and crisp, a tie will always be complementary. Sure, gingham check with a tie works wonders. It's become somewhat perfunctory, if you will. Now, a plaid shirt and a tie? You're definitely stepping into quirky territory and it is important to strike a balance that highlights your look in the right way.
A plaid shirt is always going to be bold. It stands out and if it's going to be paired with a tie, then the tie must be simple and dark, so as to tone down the bold colour of the shirt. The combination works in a complementary way if the shirt and tie have at least one of the same colour.
The efficacy of some of these combinations is in how the rest of one's outfit is executed. Therefore, jeans, a cardigan or a v-neck jersey will be appropriate at times. When dressing it up then a sports jacket and chinos will be the ultimate complement. It even works with a suit because the only out of sorts piece is the plaid shirt. With endless possibilities, however, the perfect execution will most definitely redound.
PG: Man to man, generation to generation.