Mr. Bailey was the emergency contact for me in 1st grade and once when I was "sick", he got me out of school and let me have chocolate ice cream and play Nintendo. Since that day my loyalty has never faltered. We even have a secret handshake, still implemented to this day. Great laugh, great guy, great style (and he has an even more stylish wife, of course!).
Winston's War: Churchill, 1940-1945 ($24); Hermes silk twill tie ($170); Vintage Persols circa 1980s ($199); Needlepoint Retriever key fob ($45); Belgian shoes ($350); Cartier Tank Francaise; Oliver Peoples tortoise glasses (prices vary); Dunhill cigars ($228 for box).