10 Winter Must-Haves for the Stylish Chicago Man

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• Canada Goose Parka, $745
  "This Canada Goose parka is the puffa daddy. Our friends from the far north know how to brave the cold: a down-fill
• C.O. Bigelow Rose Salve, $6
  "America’s oldest chemist has been dispensing its remedies since 1834. If there is another Polar Vortex forecast, get your dry and chapped hands
• London Undercover umbrella, $275
  "A cheap umbrella from your local bodega is a false economy. One strong gust of wind and it will flip it
• Patagonia lightweight gilet, $200
  "Now is the time to invest in a padded vest, known in Europe as a “gilet”. Suave Italians have led the charge in layering gi
• Loro Piana cashmere scarf, $450
  "There are times when it’s inconvenient to be laden down with bulky layers or a heavy coat. Perhaps you don’t want to line up
• O’Keeffe brogue boots, $825
  "So you’re either aquaplaning in leather-soled shoes or clogging about in hefty mountain boots? You need the durable u
• Le Chameau wellington boots, $400
  "There are some days when the snow is so deep or has turned to gray slush of such deceptive depth that you
• Dents touchscreen gloves, $130
  "These smart leather gloves are cashmere-lined to keep your hands from going blue in the wind-chill. And, adding
• Canada Goose hat, $250
  "We wouldn’t recommend wearing this at the same time as your Canada Goose parka––someone may mistake you for Donald Trump.
• Bowers & Wilkins headphones, $200
  "These oversized over-ear headphones double as earmuffs. Except without the dent to your street cred. The pads are mad

It's November, which means most Chicagoans are once again venturing into their coat closets and preparing for another lengthy season of snow and sub-zero temperatures. But as most who live here will tell you, it's not just the piercing wind that makes life gloomy, but the long commutes on crowded trains, sudden shifts from frigid air to powerful radiator heat, and wet shoes caked in street salt and ice. Braving a Chicago winter can be brutal, but it doesn't have be done without style.

With all this in mind we took our concerns to men's retailer MR PORTER. "For many, winter is a time when fashion comes a sorry second to function," says Dan Rookwood, US editor for MR PORTER.COM. "Piling on layers can mean waddling around town like the Michelin Man… The skill is in layering correctly using lightweight garments that are as quick and easy to remove as they are to put on, such as vests and scarves."

To help, Dan points to brands such as Patagonia, Stone Island and Canada Goose for what he describes as "temperature-regulating technical sportswear that performs with panache." Below, he details some his favorite pieces for every man this winter. Though he does add that "If all else fails, carry a hip flask––at least you can warm your throat."—Courtney Ryan
· MR PORTER [Official Site]
· Where to Buy Cute and Warm Coats in Chicago [Racked Chicago]
· Stylist Heidy Best Shares 5 Best Buys for Fall and Winter [Racked Chicago]