Best Bet: Ryder Rain Boots

In a notoriously rainy season, it seems like we’re wearing wellies every other day. Banana Republic’s Ryder rain boots pass for a classic riding boot, but still keep you dry in a drizzle or downpour. The boot features a one-inch heel (the sole is made of slip-resistant rubber) and brass hardware, so you can get away with wearing them to work or happy hour. The waterproof upper is less bulky and more breathable than rubber, but it won’t soak up subway grime like leather or suede.

Ryder rain boot, $98 at Banana Republic or online.