Q. How important is wearing current (or at least recent) styles? Some of my favorite clothes and ones I think I look best in are over 10 years old. These include a suit, some white-collared dress shirts, even a lumberjack shirt.
A. One of the great advantages of men's dressing over female dressing is that very few clothes actually go "out of style," even over a span of 10 years. It is not at all necessary to get rid of a garment that you like, and particularly, one that you look good in, just because it is not a recent purchase.
Of the items you mentioned, suits hardly change at all as to which colors and cuts are popular. The same three classic colors -- blue, gray and khaki -- are as basic today as they have been for many decades. As to cuts, there still are the two types: single-breasted and double-breasted. Here, because double-breasted cuts are trendier, there may be a bit more of a difference. That is, they are not as popular at the moment as they were 10 years ago, but they certainly are not dated looking. Stores aren't selling as many as they were a while back, but if you have a double-breasted suit you feel good in, there is no reason to feel you should not wear it.
One aspect of suit wearing that has changed is fabric/patterns. Some fabrics last many decades, particularly those without patterns, but a bold pinstripe might seem a bit out of date. Today, it is only the very rare occasion when a man might wear a navy pinstriped suit. Somehow, this look is just too formal for almost every situation you can imagine. If the occasion is too dressy for a solid dark suit or a subtly striped suit, then perhaps you should consider whether black tie is called for.
As to the white-contrast-collared shirts you mentioned, even though these, too, are less popular today, they are not an out-of-date look. Fine stores still sell them, and many well-dressed men still buy and wear them, because the truth is they are definitely a flattering and sharp look.
Lumberjack shirts are as classic a part of casual dressing as I can think of. They are neither a trendy nor a sloppy look. Unlike some forms of "street dressing," they qualify as acceptable in a great many casual situations, especially at this time of year in colder climates. They and other oversized plaids are pretty basic, as long as they are not frayed or overly wrinkled and looking past their prime, and as long as you are well groomed and neat when you wear them.
There is a mix of people who think that styles never change, and other people who, when they see current styles, think, "Wait! Didn't I see this 20 years ago?" To an extent, both are right. Again, your lumberjack shirt is as in style today as it ever was.
On the other hand, there is one category that shouts loud and clear to the world that what a man is wearing has not been purchased in the last 10 years ... a too-wide necktie. In-style ties can vary from 2 ¼ inches to 3 ½ inches at the widest part of the tie. Trendy ties can be narrower, but much wider ties just look ancient.
At this season of the year, it's a good time to take a little inventory and see what you have in your closet that you can wear, that you can work with in combination with the rest of your wardrobe, or what you would do well to give to Goodwill. The question should be, while looking in the mirror, realistically, "Does it look good?" If not, purge it; if it does, wear it.
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High Profile on 11/26/2017