Cantabrigian
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...I posted this shirt as an example of the English checked shirt chic currently in vogue with the NYC professional set with or without a jacket and tie.
There must be various non-intersecting professional sets in New York...
The only people I know who would wear a check like that in NY are from England (or at least a cricket-playing colony) and are generally middle-aged. To pull the look off, you can't even own collar stays, much less wear them and you have to be constantly shouting into your blackberry while lifting pints at some a cougar bar in a trendy neighborhood.
The key to checks, in my opinion and as I've seen them worn, is subtlety.
I like the one Jonathan posted though in small checks, I'd go even a little smaller.
Large checks really don't work. Anything that pops out at you folded up or in a swatch book is probably a bad idea.
I'd recommend something like these - classic check patterns that are definitely interesting but avoid garishness and allow you to pair them easily with a tie and a suit.
Thomas Mason - Goldline:
(from Albini's website)
(^^^I wouldn't rock the bottom one with a tie but the others are fine IMO)
Thomas Mason - Silverline, if you're talking about checks it doesn't get any more classic than these:
(from My Tailor)
http://betadn.mytailor.com/images/Fa...0,250&cvt=jpeg
http://betadn.mytailor.com/images/Fa...0,250&cvt=jpeg
http://betadn.mytailor.com/images/Fa...0,250&cvt=jpeg