Wearing boots does not make a man more (or less) masculine.
Masculinity is a set of characteristics that is demonstrated by self-confidence and a secure nature. Physical characteristics play a part, as well – how a man appears to others, including the style of dress – influences perceptions of masculinity both for the guy and others observing him.
Boots are a part of a man's choice of style of dress. Looking back over the ages, men wore boots. From soldiers to cowboys to construction workers – all considered to be “masculine” professions – men in these occupations wear boots. Boots convey a strong sense of masculinity. When one thinks of masculinity, words such as honor, courage, strength, and gallantry come to mind. A man with these qualities is the kind of man that many men aspire to be.
Simply wearing a pair of boots does not “make” someone masculine. Boots, however, are something worn with clothing that has a masculine appearance: jeans, leather, uniforms, or even business suits (a uniform of sorts). How a man behaves and projects himself has more to do with his perception of being a masculine man than what he wears.
Note: some of this content taken from a string of conversations posted on the “Boots on Line” board in 2009.