Woolrich plaid button-up shirt jacket, $65
from The Backpacker
Columbia pullover fleece, $70
from The Backpacker
North Face buffalo plaid jacket, $90
from The Backpacker
Jackets under $150
Howler Bros elbow-patch half-zip jacket, $125
from The Backpacker
True Grit woolly jackets, $145
from Carriages
North Face heather gray Denali jacket, $148
from The Backpacker
Jackets under $250
North Face merlot down puff jacket, $199
from The Backpacker
Ralph Lauren olive green utility vest, $225 (shown paired with a plaid button-down)
from Carriages
Peter Millar green utility jacket, $235
from Carriages
Peter Millar bomber jacket, $250
from Carriages
Splurge
Billy Reid peacoat, $325
from Carriages
Bates & Thigpen tan camel-hair blazer, $450
from Bates & Thigpen
Tan overcoat, $998
from Carriages
Samuel Sohn blue cashmere blazer, $1,250
from Carriages
This article was originally published in the December 2016 issue of 225 Magazine.