Feeling a bit hesitant to dive into the mad plaids of fall? This rain-resistant beauty offers a discreet nod to the Northeastern working man's trend with its flannel lining in hunter's vest orange. Designed by up-and-comer Hyden Yoo, who describes his label's look as "Brooklyn hipster meets Wall Street," the nylon jacket (with its cinched-waist and pleated pockets) looks like what we'd expect if Prada took on the classic Barbour jacket. Well done, Mr. Yoo. $322, at Oak, New York.

• Check This Out: The final week of the Fall Buying Guide explores the season's plaid trend.