Every person has a different idea about what dated is. I think Denise follows trends very carefully and, for her, something from a few years ago might seem dated (in terms of her understanding of what's trendy AND her style, e.g., she is really into voluminous, slouchy t-shirts currently). For someone else, the same t-shirt might seem very up-to-date, because maybe she was hiding her body in boxy t-shirts from Land's End for the last ten years, and just recently decided to try to wear more fitted clothes. You know?
I think Angie has made a distinction between "on trend" and "in style" (if I am remembering this correctly.....too lazy to try to do a search...). On trend refers to items or looks that are of the moment and quite trendy (e.g., slouchy trousers); in style refers to things that are no longer so hot, but nevertheless are still in style (e.g., skinnies); and dated would be something from a different era that looks bad to our eyes today (e.g., uniformly faded, high-waisted, loose-in-the-thighs, tapered Mom jeans).
But even with something like skinnies, which have been around for a while, you can still look at the fall fashion shows and see skinny stovepipe trousers all over the place. What I mean is that lots of different styles co-exist and are of the moment--you can find examples of all sorts of trouser styles on the runways. Another example would be midi skirts or dresses. They are having a moment, but other styles that are above the knee are still very popular and everywhere in the shows. A designer might show one look with a longer, midi skirt, then the next look down the runway is a shorter skirt. It's the *dominant* style or the style that catches bloggers', editors', and stylemakers' eyes that gets touted as trendy or modern or of the moment, but that doesn't mean that other styles aren't just as fab and current (as shown on the most recent runway shows, hot off the presses). There is a huge investment in keeping the giant fashion engine roaring and moving along, and new things must come out and be "obsessed over" every few months, in order to keep the engine fed.