We can’t quite put our finger on it, but there is something innately different about a city winter. The snow falls beautifully on building facades and sidewalks, and then disappears—or morphs into slush—as the streets become inundated with people and vehicles. Or there’s the cold that can quickly turn to warmth depending on how many people join you in a crowded area. No matter what a city winter may bring, good or bad, a new season is an opportunity to refresh your gear. Though it may be hard to have swag when you’re shivering profusely, don’t put baby (a.k.a. your style) in the corner just because it’s a little nippy outside. Instead, follow this illustrated guide to braving a city winter in style.

Illustrations by Greg Matesich