Dear Shopping Savage,
What is madras plaid? I've seen a few guys in shirts, blazers or shorts and was just curious. Is it similar to seersucker? It looks pretty cool and I'm thinking I want to start wearing it. Have any suggestions on how or what to wear it with?
Madras plaid is similar to seersucker in that its a lightweight cotton fabric worn in warmer weather seasons, primarily spring and summer. Its also similar to seersucker in that its favored in the south and by the preppy sect of society. But that preferential treatment and regional designation shouldn't deter you from wearing it. Madras doesn't speak to everyone's sartorial senses so if you think you can wear it, then by all means have at it.
Now, how to wear it. Since the patchwork pattern already has a lot going on, you'd want to look at pairing your madras pieces with solids to let the patchwork be the dizzying focal point of your outfit. If you opt to buy madras shorts or pants, any solid colored polo or oxford would do. The same rule applies for madras shirts: plan to wear solid pants or shorts. (Rarely can one pull off critter pants paired with madras but if you want to go completely p-p-p-p-Preppy then here's your chance.) A madras blazer could be worn with just about any outfit as long as the top and bottom in question are solid in coloring.
If you're looking for an easier transition into the unplanned plaid pattern, look for a necktie, bow tie, belt or even shoes made from madras that you can accessories an outfit with that would be considered plain without the plaid. Where the comparison with seersucker goes completely out the window is when someone wears a madras blazer and pant together. Wearing a "patchwork suit" is borderline reverse snobbery at its best, but there's only so much pattern the eyes can take in at once. And if you want to look like a well-groomed hobo then again, by all means have at it. Just don't be surprised if someone drops a quarter in your cup of coffee.