School shoes are going to be worn a lot, so they have to be comfortable and durable enough to cope with day-to-day wear.

Leather shoes by Fratelli Rossetti, $620, 212-888-5107 The Chelsea Boot When it's so cold you can feel the wind through your laces, you know it's time to switch to Chelsea boots.

Roman kids wore shoes that reflected their parents' status. ... One Roman soldier had enormous feet, 2,000-year-old waterlogged leather shoe reveals; ...