Clifford writes: Is it okay to wear clothes designated for the Fall during the colder Spring days? This is the only time of year where I get a little confused. Yesterday I wore a tweed herringbone sports coat because of the chilly night wind but wasn’t sure if it was seasonally accurate.
Remember that for the most part, the seasonality of clothing is about practicality, not some arbitrary outside rule. There are a few items of clothing (holiday sweaters, white shoes, wool ties) which are very specifically seasonal. For the most part, though, you should wear what feels right.
A good guideline, other than weight/warmth, is to remember to wear seasonally appropriate colors. Spring is a time for brighter colors, fall a time for earthier tones. Your colors should to some extent reflect the world around you. So the green Barbour coat above can comfortably do double-duty in a way that a brown tweed might not. Even still, that brown tweed, brightened with the right accessories, could be just fine.