Let’s get this out of the way really quickly. Generally speaking, we believe that people should have the freedom to wear what they like. However, some items of clothing are just so completely awful, nobody should approach them even with a 10-foot pole.

Shirts and caps with funny phrases and pictures work sometimes. If they’re sufficiently witty and lighthearted. However, the facepalm-worthy captions that we see in this list should never have seen the light of day. We’ve called the Fashion Police, as well as the Humor Bureau, and they said they’re on the case.

The ‘Boomer Core’ social media project is actually fairly new. It was created just a few months ago, in July of 2022. In that time, the account has grown to nearly 63k followers.

The founder of the page describes the project as dedicated to sharing “all the boomer images and clothing found across this accursed land.” We assume they mean the United States because we really don’t see anyone else coming up with similarly cough ‘creative’ cough shirt slogans.

The renowned philosopher Socrates had this to say about the younger generation around 470BC: “Children; they have bad manners, contempt for authority; they show disrespect for elders and love chatter in place of exercise. They no longer rise when elders enter the room, they contradict their parents and tyrannize their teachers. Children are now tyrants.”

Not much has changed in terms of inter-generational dynamics since then, has it?

Though there’s a bit of flip-flopping between academics as to how exactly we can categorize Millennials and Zoomers, there’s a lot more clarity when it comes to Baby Boomers.

Baby Boomers, colloquially (and somewhat disparagingly) known as Boomers, were born between 1946 and 1964, right after the end of the Second World War, as the Cold War was starting. They followed the Silent Generation and preceded Generation X.

In this day and age, there’s a lot of tension between Boomers and members of younger generations. Many people feel (whether correctly or not) that Boomers, especially those in the United States, are slightly hypocritical. They grew up during a time of unprecedented growth and affluence. Housing and education were cheap back then.

Compare all of that affordability back then to the economic situation now. Many young people in the West feel like they’ve been completely priced out of the ability to own property. Rent prices alone are sky-high (if you can find an apartment at all due to the huge demand).

Many Americans are also saddled with huge debts from going to university. Student loan debt in the US stands at around $1.745 trillion. That comes to an average federal student loan debt balance of $40,780, including private loan debt.

CNN really put it well when it comes to the current attitudes surrounding property. “A little over a decade ago, the dominant narrative about the housing market was that Millennials simply weren’t buying. They were either too cheap, lazy, or itinerant to commit to something as weighty as a mortgage,” writes Allison Morrow.

“Cut to 2020 and that narrative got flipped on its head. It wasn’t that Millennials didn’t want homes in the suburbs, they just couldn’t afford them. But when the pandemic hit and demand for property exploded, the furor was driven by people in their 30s—finally flush after years of slogging away at whatever jobs were left for them in the fallout of the Great Recession, and, for many, eager to flee to the wide-open spaces of suburban life.”

Morrow continues: “As that 2020 housing boom begins to go bust, those who managed to close on a home in the crush of competition fed by rock-bottom mortgage rates should count themselves extremely lucky.” Fast-forward to 2022 and pretty much everywhere you go online, you feel a sense of barely-disguised financial dread. Some Millennials and members of Gen Z feel like they’ll never be able to own an apartment or a house, and they’ll have to keep renting forever.

In this context, it becomes easy to get mad at Baby Boomers who already own their house and are already enjoying the perks of retirement. When they tell someone else that they’re supposedly not working hard enough, they completely ignore just how much the economic climate has shifted. It is incredibly hard to make a decent living with hard work alone. You’re simply not guaranteed a stable and comfortable life as much as you’d have been half a century ago.

However, at the end of the day, different generations simply have different experiences and values. Though, to be honest, nobody should be wearing any of the shirts and hats in this list. Ever!