Chicago in October is the city at its most confusing — and I mean that as a compliment. One afternoon you’re walking the Riverwalk in a light sweater, sun bouncing

Let me be honest: the first time I packed for Seattle in September, I brought a suitcase built for Italy. Linen dresses, sandals, one thin cardigan “just in case.” Big

Let me be honest — I almost skipped San Diego on a recent California trip because I assumed September meant “summer’s basically over, right?” I could not have been more

Let me be honest — I underestimated Los Angeles the first time I visited in September, and I say that as someone who thought I understood warm weather. I’d packed

Let me be honest — nobody believes me when I tell them September is San Francisco’s actual summer. I didn’t believe it either the first time someone told me, standing

Let me be honest — I packed all wrong the first time I went to Vegas in September. I showed up with a suitcase full of “cute fall outfits” because,