Menswear Dog: Land's End Canvas, $49
Next Level: J. Crew, $98
You Only Live Luxe: Engineered Garments, $204
Need to ride that line between rugged and dressed up? Enter the chambray shirt. Believe us, every #menswear dude has a couple. They can dress up with a tie or be rocked untucked with the top buttoned fastened—like a proper cool guy.