Reader Mail seeks to answer life’s sartorial curiosities and other perplexing material issues.
I was wondering if you could recommend some casual shoes for the upcoming colder months. Up until now I’ve been wearing top-siders, and with the weather lately, they’ve left my feet cold. I just need something casual that I can wear with jeans and khakis.
Samuel — New York City
The transition to fall footwear can be an awkward one. You don’t want to rock the snow boots on a sunny September day, but at the same time you need to make sure your warm weather shoes are seamlessly shelved until spring. The good news is, casual fall footwear options abound. So there is no reason you can’t be comfortable, function and stylish come cooler temperatures. My short list of laid back fall classics are are below.