Shoes and hems for a cold, wet day
The shoes and the bottom of your outfit meet the weather first. On a cold, damp day, decide how to keep socks and hems comfortable before you settle on the coat. Rain intensity, puddles and whether you can change indoors are more useful inputs than the name of the season.
Match the shoe to the route
For mostly sheltered pavement, a closed shoe you already trust may be sufficient. If you regularly step through puddles or slush, use a boot with coverage suited to the route and check how it grips. Try it with the socks you will actually wear. Thick socks that crowd the toe box can make a familiar shoe uncomfortable; use another combination if your toes cannot move freely.
Set the hem with the boot on
Choose trousers that clear the ground while walking and cover the area you want covered when seated. If a wide hem swings into a puddle, a narrower leg or shorter hem can be more practical. Above that, use a warm base and outer protection suited to the forecast. An umbrella is useful when you can keep a hand free and the wind allows it.
Make an indoor plan
If you need a different shoe at work, pack it separately and know where the damp pair can go. Carry dry socks when getting wet is likely. At home, dry footwear according to its care instructions so the same pair is ready for the next day.