“For me, a tuxedo is a way of life. When an invitation says black tie optional, it is always safer to wear black tie. My basic rules are to have shirt cuffs extended half an inch from the jacket sleeve. Trousers should break just above the shoe. Try not to sit down because it wrinkles the pants. If you have to sit, don’t cross your legs. Pocket handkerchiefs are optional, but I always wear one, usually orange, since orange is my favorite color. Shine your Mary Janes on the underside of a couch cushion.”
1. It takes two hands to put on a hat the right way: Back brim curled up, front tugged down to a couple of inches above the right brow.
2. Never wear brown at night. Never.
3. There’s no excuse for brown shoes past sundown.... Or white shoes. Or anything gray, unless it’s deep charcoal. Or blue, unless it’s midnight blue. In fact, let’s keep it simple: after dark, men should wear black.
4. Ties should be silk. And conservative.
5. Cuff links always. But leave the fancy jewelry to Sammy.
6. When dressing formally, a vest is better than a cummerbund.
7. Don’t wear a tuxedo on Sunday.
8. Having messy closets is like putting on clean clothes over dirty underwear.
9. The shower is a great place to steam out the wrinkles in your dinner jacket.
10. Orange is the happiest color.
11. Don’t hide your scars. They make you who you are.
12. When it comes to pockets, everything should have its own place.
13. A pocket handkerchief is essential, but it needs to be perfectly folded.
14. Shine your shoes.
15. Trim. Buff. Clean.
16. Take your hand off the suit, creep.
Adapted by Sinatra from The Way You Wear Your Hat, by Bill Zehme