Ask the MB: October Booze Cruise
A: We're on record advocating for gingham as a year-round pattern, so definitely wear that shirt.
If you really want to hit it out of the park -- essentially becoming your office's Mr. October -- pair it with a brown corduroy blazer, like this one from Banana ($198), or this one from J. Crew ($138), or if you're flush this one by Etro ($990). It's the cocktailing equivalent of mixing ginger into bourbon lemonade; you're hitting the appropriate fall notes while your shirt and leisure activity read summer (and you can wear that blazer for the next 5 months).
Suddenly we're very thirsty.
UPDATE: The J. Crew version is now on sale for $99, $109 for Tall.