Buy a suit that fits your build and it will never look too far out of place. Don't buy exaggerated cuts (like the present too-tight fit with too-short pants). The trendiest items will always be a little different, but they don't vary too far from the middle. You only look silly when you buy clothes too far on one extreme and the trend moves to the other end.
I'm not doing it at all. Jeans, t-shirts, occasionally a simple two-button suit, if required.
But for a lot of management guys, especially in finance, not being "too far out of place" just doesn't cut it. Somewhere you have to be more conservative than the general fashion, somewhere your tie and lapels have to be the proper width of the season. Never mind the often considerate difference between British, Italian and American fashion. We're talking about business fashion, not artist/actor style. (Never mind the preppy side of all those style guides and blogs.)
I'm not arguing about the timeless cuts, I'm a big fan of the toned down British style. And given the audience of this site, it's a good suggestion. Basically the 80/20 solution of menswear.
But it's really not like you've either got timeless fashion or 70s brown checkered suits with bell bottoms.
Buy a suit that fits your build and it will never look too far out of place. Don't buy exaggerated cuts (like the present too-tight fit with too-short pants). The trendiest items will always be a little different, but they don't vary too far from the middle. You only look silly when you buy clothes too far on one extreme and the trend moves to the other end.
See here for examples: http://theimpossiblecool.tumblr.com/