At Context, a five-year-old boutique in Madison, Wisconsin (113 King St.; contextclothing.com), owners Ryan Huber, Sam Parker, and Ben Parker preserve the traditional American heritage style better than anyone else in the country. The “trad” look has taken over men’s closets on both coasts, but this time Midwesterners deserve credit for being ahead of the trend. After all, guys from these parts actually hunt, fish, and work outdoors. We asked Huber, also Context’s creative director, to ID what our boys need to build (or tweak) their classic, weather-ready wardrobes.

PATTERNED OXFORDS Huber recommends checked fabrics and plaid flannels ($176) from the Pennsylvania shirt makers Gitman Vintage. Layer with a Donegal tweed overshirt ($225) when temperatures drop.

RAW DENIM JEANS Context’s 2010 collaboration with the Japanese denim company Momotaro features handwoven near-black indigo jeans ($320). Fade to your taste.

AMERICAN WORK BOOTS Alden Shoe Company’s handmade Rough Roy work boots ($445) make a brawny comeback with heavily oiled, mill-dyed chamois leather that “ages” after just a few wears.

ALL-PURPOSE PARKAS The English outerwear designer Nigel Cabourn’s Everest parka ($2,600) was modeled after the coat Sir Edmund Hillary chose for his 1953 ascent of Mount Everest—surely enough to fend off even the worst Chicago chill.

Photograph: Phill Lee