Depends on one's definition of "trendy", "stylish" and "chic", doesn't it? Innately chic and stylish people generally do their own thing and can generally look chic and stylish in flipflops, a garbage bag and a length of string. Trendy people are usually trying a bit too hard.
It also depends on how comfortable one feels. I always feel like "the accused" in the majority of "designer" suits - usually cut to suit the undernourished silhouettes preferred by a certain kind of menswear designer and often made of shoddy materials - which is why I tend to wear tailormade suits of a very conservative cut. I am sure all these suits are highly "trendy" and "stylish" but I feel not unlike a dog's dick in an inappropriate setting when I wear them. However, more power to people who feel and look good in them. Same goes for Converse versus modern trainers. Wear what you feel comfortable wearing and you will generally look and feel good. You know the story about Beau Brummel, don't you?
BB was out promenading along the Brighton seafront one morning with a friend when they encountered some acquaintances, one of whom complimented the famous dandy on his cravatte. BB thanked him graciously and when the aquaintances had gone on their way, turned to his companion with an perturbed look and insisted that they return home at once. Asking why, the companion was told by BB that he simply had to change. The reason? They had noticed his cravatte...which meant that the cravatte or the outfit, or all of it, just wasn't working. There's a moral in there somewhere. Something about keeping it low key.
It's not about the shoes...
PK