Fascinating comments from everyone. (And thank you Taylor for posting that link--I have been so curious to see your style. VERY sharp! I REALLY enjoyed those photos.)
To answer Angie's original question, no. But I do acknowledge there is a certain bias against classic dressing, as if it doesn't show one is up with the times, the way Frances described it.
Personally, I love fashion and shopping but have limited funds to spend, so I really don't like to buy anything that I am not sure I can wear for years. Having said that I don't like generic clothes, so I always look for details, like a special color, print, fabric, seaming, hardware, etc.
I think how stylish I find classic dressing depends on how much the person owns the look. If they are dressing exactly right for them, then it is equally as stylish as a trendy look. By the same token trendy can look like a fashion-victim when the clothes are wearing the person. I think it comes down to knowing yourself. One of the styles I admire most in other people is those who have figured out a uniform that works for their lifestyle. So keeping, let's say, a constant silhouette for work, like a certain shoe, cut of pants, blouse, belt, overcoat, that is perfectly adapted for that person's life. Another example is having only a few different outfits but every outfit is PERFECT. I met a woman like this once, where she seemed to have 3 work outfits, and then socially, once I saw her wearing something else, but every outfit was perfect for her and for the occasion. I like change too much to dress that way myself, but my point is, I think classic style can mean knowing yourself. Knowing exactly what works for you and sticking with it over the years with tweaks to acknowledge the times.