It's time to roll up those cuffs and throw on some booties!

There are people who roll up their pants and expose their ankles to the elements in the dead of winter. It’s their prerogative, but to me it seems insane—as strange as those bros bustling around outside in cargo shorts and flip-flops on the first day in March when the temperature finally breaks 40. Then there are people who wear closed-toe shoes and long pants all summer long. Again, their prerogative, but one gets to wondering if they’re religiously observant, or if they’ve experienced trauma, or suffer from a draconian corporate dress code or a dreadfully over-air-conditioned office, or whether they’re so unnaturally cold they prefer, even enjoy, keeping themselves wrapped up during heat waves.

For me, there’s a definitive time and place for closed-toe shoes to merge with pants rolled up at the ankles—and that’s a dry, 55-degree day in Chicago. Bare-ankle season comes twice a year, but it’s in the fall, when the trees aren’t naked and radiating the chill of winter, that it’s particularly pleasurable. To throw on some sneakers or oxfords or booties, to roll up that pant leg, and to stride outside in a light jacket over a long-sleeved shirt knowing that you will spend the day neither freezing nor melting, with the light natural ventilation of the wind at your ankles, is to truly feel alive! You get to experience the rare pleasure of comfort in your body, clothes, and environment all at the same time.

A dry fall day is also when I get to dust off the most interesting, comfortable shoes I own, without worrying about the possibility of sweating through them or muddying them up or ruining them with salt or getting overheated. A dry fall day means no more wondering if my unpainted toes look weird in those sandals, the second one tempting fate by sticking out over the edge of the sole. No more need to resist—or cave—to the idiotic social pressure of shaving my legs. In the fall, when bare ankles—naturally elegant no matter who you are—become the centerpiece of your look, the rest of your body can relax.   v