Just like when your aunty Doreen joined Facebook and started incessantly poking you, or when everybody suddenly had one of those Michael Kors bags, it can be rather easy to make something uncool.
Just ask Fred Perry, who has long battled to rid the brand of its "skinhead" association.
Now the brand has had to defend itself against gaining a rather unfortunate reputation as being the outfitter of choice for the so-called "alt-right" (folk who associate with far-right and racist ideologies – the kind who read Breitbart and can often be found harassing women on the internet).
This time it was down to an alt-right offshoot called The Proud Boys, self-described "Western chauvinist" lads who are, as per their Facebook page, "anti-political correctness, anti-racial guilt," and rather pro- Fred Perry polo shirts. The group can often be found wearing black ones with yellow trim as a uniform of sorts.
The group, founded by former Vice Media founder Gavin McInnes, recently disrupted an Indigenous protest ceremony on Canada Day, sporting their beloved Fred Perry black polo shirts and a Red Ensign flag (a former Canadian flag used by federal government that has been co-opted by the far right).
The act forced the chairman of Fred Perry, John Flynn, to make a statement distancing their brand from any Proud Boys association.
"It is a shame that we have to even answer the question.
"No, we don't support the ideals or the group that you speak of. It is counter to our beliefs and the people we work with."
As Flynn notes, the brand was started by triple Wimbledon champion tennis player Fred Perry in 1952, and since then has been associated with both mods and skinheads.
It's certainly not the first clothing brand to become something of a preferred supplier to extremist groups.
As The Washington Post notes, Dr. Martens boots have had a long association with skinheads and neo-Nazi blogger Andrew Anglin declared New Balance sneakers (an American-made brand that had been enjoying a sudden rush of chic after being adopted by the fashion crowd) to be the "official shoes of white people" after the shoe company appeared to support Trump after he was voted President-elect.
(The company later clarified that an apparently pro-Trump statement by its head of public affairs, Matthew LeBretton, was only in reference to Trump's trade policy.)
It's a conundrum that Andrew Hughes, a lecturer at the School of Management at Australian National University, believes is going to become trickier as brands become ever more ingrained into our values. As in, I shop (this polo), therefore I am.
"This space is becoming ever more important to consumers," he says, adding that what we buy is no longer necessarily a utility function, but a statement about who we are.
These purchases aren't a "narrow part of our lives, but an experience; transcending functional use." This means that brands, which no longer just sell us stuff but have a personality that we try and match to our own, more than ever need to be aware of this.
Which is very tricky. It can all go so terribly wrong, as Pepsi's ill-thought-out ad starring Kendall Jenner co-opting the resistance with a can of fizzy sugar water showed.
This is the case, says Hughes, even when it's not the brand itself doing the associating. Perception after-all, and especially in fashion, is everything.
So can Fred Perry recover from this murky association? Yes, says Hughes. But it needs to be done in an authentic way.
"They need to say it's not what we stand for ... and show actions, not just talk about [it]."
Hughes suggests taking action such as starting some kind of charitable foundation, empowering staff to give back to the community and engaging in conversations - from both sides of the spectrum on social media.
It's a view shared by fashion PR Adam Worling.
"I commend Fred Perry for being proactive and distancing themselves from the values of the alt right," he says.
"I would expect that Fred Perry will back this up with a campaign that makes the alt-right feel uncomfortable to wear their designs."
Recovering from a branding misstep is something that the fashion industry can do well.
In a less extreme way, it was a similar story a few years ago at Burberry in mid-2000s when hooligans and D-listers alike shared a fondness for the heritage British brand's iconic check, diminishing the brand.
Success became a burden, as marketing professor Ketty Maisonrouge told the New Yorker: "It was so successful that everyone had it, and if everyone has it then the people who normally can afford luxury items don't buy it."
The company's fortunes (and fortune is perhaps relative, because you could be making a fortune selling a billion Burberry check dog leashes but is that meeting your brand objectives?) were turned around when Angela Ahrendts, the brand's CEO until 2014 when she moved to Apple, and the brand's current creative director Christopher Bailey restored the house to its heritage – quality trench coats made in Britain, understated luxury, craftsmanship.
As Bailey once told the New Yorker of Burberry's appeal: "it's for the young, it's for the old, it's for the city, it's timeless, it's ageless, it's been worn by everyone from Princess Margaret to Sid Vicious."
So what then makes something luxurious? Or cool? Or deathly uncool?
Partly it's to do with creating a club (or if you're a Proud Boy, a rabid kind of frat) – the sense of belonging somewhere that others don't. As the New Yorker noted, Tiffany & Co is a brand that has managed to be both mass and exclusive; plenty of people buy the tag charm, only a few buy the most rare and precious pieces (and they have their own viewing room).
And it can work in reverse too. Look at the resurgence of brands like Fila: once the shoe of choice for suburban dads, the brand became cool when Russian designer Gosha Rubchinskiy reworked them, and a range of sweatshirts that were sold at the very cool Dover Street Market in London.
As Matthew Schneier pointed out in an examination of the coolest man in fashion right now, Demna Gvasalia, "Of course, when cool becomes profitable, it also becomes a commodity."
Which, arguably, automatically makes something less cool – which makes the definition of cool or desirable difficult to define. But what really matters – especially now – is if something is authentic.
And for better and sometimes a whole lot worse, whether it is in some way, an expression of who you are, and what you stand for.