Wearing an ascot (and probably wearing a formal cravat) after 6 pm with a tuxedo is “breaking the rules” and will definitely dress down your look. I advised against wearing an ascot to any formal occasion that would be well documented precisely because your outfit may look dated. That said, life is no fun if you never take risks and from my perspective style doesn’t mean always playing it safe. Fashion, style, and taste would never evolve if we continued to wear the same things the same way.

A quick Google of “David Beckham Style Icon” will show you that I am not alone in this description of Beckham. I whole-heartedly agree that Cary Grant was one of the most stylish men of the last century. I also think you presented a great list of men who have really classic style.

I appreciate your comments and perspective. I think it is really important that anyone that reads this little article has multiple perspectives on how to wear ascots/cravats. The look is kind of risky. I think that many very stylish men I know would take your side over mine.

What? Since when should ascots be used with formal wear? It looks terrible on Beckham precisely because he tried to pair it with formal clothing (you can see the shiny peak lapel of what appears to be a dinner jacket), making it appear out-of-place. Ascots are distinctly informal, and should only be worn with equally informal clothing such as button-down collar shirts and odd sport jackets, like Cary Grant is doing in the pictures above.

Also, you might try distinguishing between fashion,, which changes year to year so that companies might sell more clothing, and style, which lasts much longer. Cary Grant was stylish, while David Beckham is merely fashionable, wearing clothing that will show its age in no time. I’ve never seen David Beckham mentioned as being considered a style icon among well-dressed men, while Luciano Barbera, Willy Brown, David Letterman, and Brian Williams are regularly noted as being a among the best-dressed men in the public eye today.

Ascots are quite hard to pull off, you are right. I noticed Chuck’s deep red pocket square does not match either the color of his shirt or ascot. Is that a common practice among ascot wearers?

Forget VBS, your husband deserves a RLBS for that one. Proper revenge would be that you underestimate his age or time-since-school the next time he’s trying to sound credible.

Of course, I never lie about my age — my birth date is numerically awesome, and I prefer to brag about it!!