<p>My son has gone without boots in Philadelphia and Chicago for the past 11 years. Sometimes his feet get cold. He hasn’t had any shoveling responsibilities recently. </p>
<p>I say let the kid find his own way. But for what it’s worth, interesteddad had a really good suggestion. Personally, I use medium-weight Gore-tex lined hiking boots for almost all my winter needs. I have a pair of waterproof classic L.L. Bean boots that I wear with multiple sock layers sometimes if I have to be in really deep snow, but that means maybe once or twice a year. At Penn, maybe there will be a day or two some years (and some years none) when the timing and intensity of a snowstorm is such that the walkways don’t get cleared before the kids start using them.</p>
<p>MOWC is completely correct that the much more annoying problem here is days when it is 35 degrees and raining. THAT is miserable.</p>