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The unexpected style icon: Adam Sandler’s influence on Gen Z fashion

See how the style of one the greatest comedians took center stage

Adam Sandler at a movie premier
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Nowhere on our fashion BINGO card did I have Adam Sandler emerging as a fashion icon. As a matter of fact,*double-checks BINGO card* yep, there it is, on our never-gonna-happen BINGO card. After COVID-19, the world has felt just a little off. The Mandela Effect seems to be all around us, and we can’t seem to find the grip we once had on reality. One of those Mandela Effects has been hitting hard since the end of last year when we could have sworn that Adam Sandler was once the most made fun of celebrity for his style or lack thereof. Adam Sandler outfits always seemed to consist of oversized basketball shorts, oversized shirts with outlandish patterns, basketball shoes good for hooping, and white socks (always white socks).

Although we didn’t see it coming, it is here. Sandler himself is constantly asked about it on his appearances on red carpets and talk shows. Even he wants to know how and why he has suddenly risen to the level of fashion icon. Here, we look at why it happened and wonder if this is temporary or if he is the newest entry into the celebrity-style Hall of Fame. He’ll look great right next to David Beckham.

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How it happened

Adam Sandler with Jennifer Aniston
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Like anything with Gen Z, you can blame social media if you are upset about his rise or thank it if you believe it is long overdue. During an appearance on the red carpet, Sandler was approached and asked if he knew what “Madam Sandler” was. We were curious, so we went to TikTok to understand, and there it was: hundreds of women donning crop tops and baggy shorts with their Crocs. What is the draw? Well, there are multiple things at work here. First, there is the trend of people intentionally dressing with the expectation that people will hate their outfits. Second, there is the ultimate focus on comfort, which has become all the rage.

There is a huge focus on loosening up. Wearing less constrictive clothing has become the new version of self-care. If you are over thirty years old, you remember when people told you that if you dress like that no one will take you seriously. Maybe that is still true, but the reality is that young people have a style all their own and they are abandoning all that we saw through the 2010s and returning to the more relaxed fits.

Will it stay?

Adam Sandler with Adam DeVine at movie premier
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This is a fair question. The truth is that trends come and go on TikTok faster than you can imagine. The shelf-life is similar to an avocado, once you notice it is time, you blink and it is too late to indulge. So the question about the staying power of Adam Sandler’s style as iconic built on the back of a social media trend has a bit of an uphill battle. However, We remember leaving the theater in the ’90s when a man-child got on the screen and poked fun at the stick-in-the-mud personality of professional golf. We also remember when that same man-child made an entire movie about a loveable idiot redoing every grade from kindergarten to high school just so he could prove he is less of an idiot than everyone thinks, all while being an idiot. We remember the old heads saying he wouldn’t last long; he was a one-trick pony. And yet, here we are, thirty years later, and an unknown amount of money has been made as Sandler is one of the leaders in the cinematic comedy industry.

We can’t imagine that young people will still wear the “Adam Sandler Special” in a few years. We assume that there will be this moment when they look in the mirror and realize they look like a manchild themselves, and for some reason, it works for Sandler but less for themselves. But we can’t ignore the fact that Adam Sandler defies all odds and knows how to stick around, and after three decades of being made fun of for his style, he is getting the credit many feel he deserves.

Should you try it?

Adam Sandler with his family
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Here it is. The question you want to know. Should you try to dress like Adam Sandler? We are of two competing thoughts here, and that means that at the end of the day, you will have to make up your own mind about whether or not this is the move for you. However, here are the two thoughts we have:

  1. Adam Sandler dresses that way because he has the luxury of being Adam Sandler. He doesn’t need to use his appearance to get others to take him seriously. He is Adam Sandler. When you get to the point that you are one of the most famous comedians of all time, then by all means, dress that way.
  2. Fashion is what you wear; style is how you wear it. We talk about this. We preach this. You don’t need to dress up in a suit and tie to impress. You don’t need the most expensive garments, and you don’t need to jump on the latest trends to be stylish. You just need to do what you do and do it well. Maybe that is Sandler’s secret. People are just starting to notice. One thing to keep in mind is this guy is one of the best celebrity basketball players on the planet, and maybe that is why he always looks ready for a pickup game.

At the end of the day, you aren’t Adam Sandler, so you won’t get the same kind of reaction to your comfort core look as he does. And that is ok. He has brought joy to millions for three decades as one of the funniest people ever to hit the screen and stage. He has also been unashamed of who he is and what he wears since the beginning. So maybe, in part, that second thought, the philosophy we live by, was learned from Adam Sandler himself. He is the perfect example of “fashion is what you wear; style is how you wear it.”

Mark McKee
Mark is a full-time freelance writer and men's coach. He spent time as a style consultant and bespoke suit salesman before…
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