Trying to be anti-cool is just one exponent of trying to be cool -- it's the same beast.
DAVID FOSTER WALLACE
The Chuck Taylor sneakers from Converse have been in the news lately as Ralph Lauren had to give in to Converse for ripping off their shoe design. It is an odd thing because the fashion industry really doesn't have a concept of intellectual property except regarding trademarks. But the style of the shoe is so iconic that people automatically associate it with those Chuck Taylor Converse shoes. For the moment, those shoes are really cool. But there was a time when they were really uncool, and I remember those times. In fact, those shoes were anti-cool. Kids who couldn't afford Air Jordans wore the Chucks. Punk rockers wore Chucks. This is because Chucks were cheap and still are relative to the pricier sneakers. Then, anti-cool became cool. For me, cool is just plain stupid.
The problem with cool is that it tends to make products pricer beyond their actual value. This is why an Apple computer will cost three times what a PC will cost even though 90% of what you do will be done on the internet with the same functionality as a cheap Chrome computer. Apple consumers have to lay out all that extra dough for all that extra cool. I can say the same thing about a cup of java from Starbucks versus what you can get from Dunkin' Donuts. The typical Starbucks customer lays out $2 extra for each cup to pay for the cool. Is this really necessary?
Another brand that profited from the Cool Premium was Samuel Adams beer. For a long time, the cool drinkers quaffed on Sam Adams while the uncool kids had to drink Budweiser or Milwaukee's Best. Sam Adams was at forefront of the craft beer movement. Then, SOMETHING HAPPENED. Sam Adams began to lose its cool. You can have zero cool and gain cool, but you can almost never regain it. The Boston Beer Company is looking into the abyss of being uncool. Meanwhile, Pabst Blue Ribbon continues to gain cool because of its anticool cred among hipsters. Plus, it is cheap. Yes, it is weird stuff because it is basically just beer.
There is no way to measure coolness, but it can generate or cost you a lot of money both as a producer and as a consumer. Plus, there is no enduring competitive advantage in being cool as you can just as rapidly become uncool. Those who live by the cool die by the cool. There has to be a better way.
On the producer side, I would advise against trying to be cool. Being cool is a bargain with the devil. Producers should identify their core customers and always keep them happy by offering the highest quality at the lowest price. Then, ignore everyone else. This can be unbelievably hard to do. It helps to know the difference between quality and the ephemeral.
On the consumer side, I would advise people to try and be uncool. This will save you a ton of money. When I think of uncool, the image of nun's shoes spring to mind. Nothing is uncooler than footwear for nuns.
When you are not cool, you don't have to buy the latest thing such as a smartphone. You don't buy clothes to be trendy. You find the ones that last the longest. Cool takes a backseat to things like utility, durability, and modesty. The result is that you find more money in your pockets because you are no longer paying the Cool Premium.
Every so often, being uncool becomes really cool. But you can't predict things like that. You are always better off being uncool. You can't go wrong being uncool. Be boring. Be practical. Be thrifty. Be kind. Be humble. These are good things to be. I would take those things over cool anyday.