He suggests thinking of the blazer almost like a coat: Remove it and the outfit beneath should still feel more or less complete. All three men are fans of doubling up on denim with a western shirt.

At Brunello Cuccinelli, a brand more synonymous for its relaxed tailoring and cashmere neutrals, we saw raw-edged denim. While at Dunhill, a classic houndstooth blazer and neckerchief was paired ...