I had a long hiatus between my days of commuting in Boston as a 25 yr old, and my recent recent picking it up again last year as a 34 hr old...

Boston:
-wore regular clothes, often rolled up ankles on my pants.
-rode a 1983 motobakane road bike with front brake only.
-rode only in decent weather.

Now, small-city Indiana:
-wear bike shorts,
-dress warm and ride in freezing weather
-ride a Walmart Schwinn Varsity 1200 hybrid.
-