5 "Items" every stylish man should have: (I like globetrotter's response the best so far -- most like what I'd say I think.) But if we stray from clothes to the broader "items," I'd say: (5) A classic, "timeless" watch. (Not trendy) (4) At least for those of us in colder climes, a great overcoat that fits perfectly. In black, dark blue or camel. (3) A great blue blazer that fits perfectly. I'll cheat, and say a great dark grey or navy pinstripe suit too. (2) Shoes are tough -- great shoes deserves to be on the list, but it's hard to say which ones. If I had to point to one, I'd say a pair of dark brown lace-ups, such as Edward Green Chelsea's. But I think a "stylish" man should (must) have a good collection of shoes for various seasons, sports and events -- for work and for play. (1) A "good" woman. To me, that means a woman with confidence, enthusiasm, intelligence, beauty, style and, most importantly, one with whom one has alot in common -- social, education, economic, family, religion, etc.