I spent some time in Hamburg for a while, it was around 30 deg F and very windy most of the time. I never had a problem walking around town. You could walk around all day in that weather. You can put on as many clothes as you want to stay warm. There's only so many clothes you can take off before being arrested though...
I can fix my hair with a comb at work after removing a hat, a head full of sweat is a lot worse. It's the smell that does it. There's no way to get rid of it without a shower.
I work on the West side of town though so your experience may vary downtown. It's about a 1 mile walk down roads with no sidewalks to the nearest businesses. The only people you see walking around here are lunchtime joggers, gang members and homeless people. We recently built a new building and many of the employees asked for showers for the lunchtime joggers. Management refused.