Image by Bettman/Corbis and used without permission. Let me know if it has to come down, please.)

Can a man pull off wearing a hat forty-eight years after President Kennedy killed the practice? Do you think we’ll see President Obama taking the victory lap in his topper after taking the oath of office? I doubt he’ll wear the Sox cap with his topcoat, no matter the weather.

Which brings up a point, by hats I mean hats. Not caps, be they baseball or flat. I mean fedoras, trilbys, skimmers, cokes (bowlers), Lord’s, porkpies and Homburgs. After all, you can’t wear a cap with a trenchcoat or a raincoat. It just doesn’t look right.

But hats can be difficult to pull off. Mr. Grant does nothing to detract from his famous mug. He carries his in several scenes from “Indiscreet.”

Yes, hats can be tough. Especially if you, like I, wear glasses. A hat ages me quickly.

But today it was raining. And my dog’s birthday. He deserved a walk regardless of the weather. So on went the Barbour jacket and the faithful Borsalino waterproof, crushable…

… that’s been around the world with me.

France, 1997

I must have a dozen hats, innumerable caps and a helmet or two. I love them all, but they rarely see the light of day. When and how do you wear your hat? Or do you wear a hat at all?

This has always been one of my favourite looks. I love a double-breasted blazer, although this is the first I’ve had made with gold buttons. The shirt is blue with a charcoal tattersall pattern. The tie is ancient B-Squared. I’m wearing gabardine charcoal brown trousers by Uomo Homme (with two and a half pleats, but they are very nicely cut and drape beautifully.) Brown plain toe oxfords.

I guess that before I knew who Alan Flusser is, this was the look that had the most dramatic impact on my developing sartorial senses.

Then, of course, there was this guy…

I’ve written about Mr. Merkin before….

And Osbert Lancaster.

All masters of mixing colour, pattern and texture. All very well dressed. They also have one more thing in common: call it “flash” for lack of a better term. Done right, this look is very sophisticated. Edward, Duke of Windsor, could (and often did!) mix five patterns into his daily dress.

But I’m changing a bit in my tastes. I’m becoming more catholic, I guess. Maybe it’s the change in the weather (they’ll be a change in me… as the song goes.) Or maybe it is my advancing years. Maybe I’m being too careful with my “public image” in a small town and not playing enough. Maybe it’s the state of the economy that makes me want to dress more soberly, but in very well-made clothing.

Because here’s where I want to go.

Grant as Roger Thornhill via urbanite.com

(via A Suitable Wardrobe. This photo now sits on my desk.)

I’m off to work on my tan. That and the simple suit and tie combinations may be as close as a man can get.

Jut thought I’d get that into your collective head for this evening.

I don’t know why, but setting the proper mood when dressing for the evening’s festivities always brings out the best in my sartorial sense. A theme like “Charade” can bring out your inner cold warrior or James Bond — all white shirts, navy suits and highly polished black oxfords. A Cole Porter tune may lighten the mood and ready you for cocktails at the local piano bar; preferably in black tie. Frank Sinatra or Dean Martin will let you ring-a-ding-ding into the night. Usually with a dressing drink while you step into your Camelot-era slim suit.

Most of the time I play music from the 1930’s through the early 1960’s, depending on my mood and the dress code for the night.

For some wonderful jazz, check out the V&A’s Art Deco Music Collection from 2003.

For some forgotten gems try a compilation like Verve’s Unmixed or Remixed series.

Or stick with the originals. The classics never go out of style.

What’s your favourite “mood” music?