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Okay — yes, yes, yes — you're smart enough to know that when people call this the "Windy City," it actually has more to do with our long history of bloviating politicians than our weather. Bully for you. Thing is, fall's forecast actually is a tad gusty (particularly down inside the Loop next to the water) and, as you know, crazy unpredictable. Dressing against the weather can be so hit or miss and, as often as not, less than chic.
Such being the case, we asked one of Chicago's more fashionable (and weatherproofed) bloggers, Sierra Widmer-Rodriguez of Style on the Line, to demonstrate proper Second City early-fall fashion via Instagram snaps. Armed with some warm, seasonal Clarks, this lady not only gave us looks that should inspire your entire season, but a list of her favorite Chi-town haunts. It's a stylish little twofer that should get your gusty fall flying in the right direction.