Trends are defined as what is new, now, and current. The one word missing from this definition is the one word that is a part of every man’s vocabulary: timeless. I am confident that a well-fitting suit will look as good as it does fifty years from now, just as it did fifty years ago.

Rewind the clock to the early 1920’s. The Great War is over. America is growing in leaps and bounds. Fashion is becoming a focus. Men are in suits that fit, with varying heights of the waistband, and varying lengths of the suit jacket. Men begin cuffing their pants at this point – something that flies in and out of vogue for decades to come. As the ’20s draw to a close, one has the options for oversized pants, cuffed high waters, and knickers. Oversized pants didn’t look good then, and doesn’t now. Cuffed high waters can be seen in the pages of a magazine today, but is guaranteed to be gone tomorrow (or maybe even sooner), and I will assume no one owns a pair of knickers who is reading this article.
As time continues, the highs and lows in trends and timelessness reveal themselves, including:
* The three-piece-suit and the double breasted suit – If you purchase a three-piece suit, be prepared to walk into your tailor (many dry cleaners offer alterations, too), to ensure a proper fit. Be prepared, also, to wear them as separates, as the cycle of the three-piece trend contains generations of people thinking it looks stuffy and/or costume like. Some choose to grin and bear it, but if you are the type of man who doesn’t wish to stick out like a sore thumb, rejoice in the suit’s versatility. Note also, everyone HAS to have the double breasted blazer now (at the time of publishing), but before you know it, it will be out of fashion again. This, sadly, is another cyclical item which many, including myself, wear with pride. It is also one that will spend a year here-and-there on the hanger, not seeing the light of day.
* Leather jackets – These never fell out of style, in the truest form of what we would call a jacket. It’s offspring, however, the leather blazer, got quite a workout in the ’90s. Where are they now, Nowhere. It is in instances like this where one can hone their trendy/timeless radar. Did something that wasn’t broken suddenly get fixed, Yes. Thus a trend, and with it an expiration date. (Note – a regular leather jacket should fit close to the body, like a suit jacket or blazer would.)
* Bell bottoms – Jeans that have an exceptionally wide flare beneath the knee have a time and place. It’s called the 1970’s, and when your Delorean can get you there, you’ll be able to pull them out of the closet. Until then, October 31st is pretty much your only remaining option.
* 6-sizes-too-big pants that fall below one’s tush, with boxers showing, AND no belt – many are unaware, but this trend began in prison. When locked up, your belt is one of the first things confiscated. This left you with your pants halfway to the ground until you got your jumpsuit. Gang members took this look to the streets as they were released, and this abomination of sartorial ignorance was born. Belt loops needs belts, pants need to be in your own size, and they need to be pulled up.
* Cuffs – I’m coming back to this trend, as Fall 2012 / Winter 2013 publications have cuffs on almost every pair of men’s trousers. In an era of cuffed pants, the man without still looks like a man wearing pants. In an era of uncuffed pants, a man with cuffs looks like he got stuck on a trend that is no longer relevant. It’s hard to resist this one, but just say no.
When you see others wearing things you wouldn’t be caught dead wearing, and then ask yourself this simple question: “In 20 years, 30 years, even next year, will someone see what I’m wearing, and think they, themselves, wouldn’t be caught dead in this,” If the answer is yes, or if there is a doubt, you may be wearing something on the trendy side, which can be dangerous territory. Tread lightly. If the terrain is too messy, though, you can always pull a pair of cuffed high-waters out of the closet from the last time anyone wore those.


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