You really can't go wrong with a solid pair of Goodyear welted plain toe boots. I find that they balance out the bulk of a heavy leather or canvas jacket perfectly without looking too formal. Still trying to figure out what my next pair should be for the upcoming colder months, honestly.
John Lofgren Monkey Boots Shinki Horsebuttt - $1,136 The classic monkey boot silhouette in an incredibly rich Shinki russet horse leather.
Grant Stone Diesel Boot Dark Olive Chromexcel - $395 Goodyear welted, Horween Chromexcel, classic good looks.
Schott 568 Vandals Jacket - $1,250 The classic Perfecto motorcycle jacket, in a very special limited-edition Schott double rider style.