Classic men’s style is well suited to scholarly erudition, based as it is in so much history and the trends that speak of centuries rather than seasons. But reading the history of men’s clothing won’t get you very far towards knowing what to wear yourself. You need both. And the best books that have been written on classic men’s style include a mix, albeit with varying degrees of success in the mixture.
It is important to know what kind of book you’re getting, and hopefully this one will give you a decent place to start.
Dressing the Man, by Alan Flusser
A practical guide to what suit to wear, what colors to wear and what combinations to make with the other parts of your clothing, all seen through the perspective of history and tradition. Entertainingly written and the only book to include pull-out sections with shirt and suit swatches, this is your starting point.