On a seemingly sunny Friday in Chicago, she slipped into her black linen joggers and a cropped black long sleeve tee, layering a crisp white jacket on top because—city weather—then laced up her ivory, gold, and taupe sneakers, grabbed her go-to gold hoops and herringbone necklace, and braced herself. Her son’s energy was off the charts, like he’d mainlined espresso in his sleep, so they hit a nearby playground before open play, and then again after play school, just to keep up with him. The skies had been all sunshine and good moods until, of course, they weren’t—no rain in the forecast, not a cloud in sight, until suddenly there was, and as their morning wrapped, they found themselves sprinting stroller-first through the neighborhood, laughing and dodging puddles, hoping to beat a full-blown, movie-scene-style downpour back home. LTKFamily LTKWatchNow LTKStyleTip