Last winter, I had no real cycling specific gear, but shorts got a week, shirts (cotton t-shirts) got 1 day, middle layer pants got a week, middle layer shirts got 2-3 days, and outer layers got about a month, cause they just got muddy and icky within a day.

This winter, with cycling specific gear I'm thinking 2 days for bottom half layers, 1 day for shirts, and prob. weekly for outer layers.

But this is more because I have laundry in house as opposed to having to bike it down to the laundromat so it's easier to do.

Gloves, hats, facemasks, etc, based off of smell.