Dads Are Sharing The Clothing Choices They Know Will Mortify Their Kids

“Dad, you’re so embarrassing!” If I had a dollar for every time one of my sons has commented on my clothing, I’d be a millionaire. A billionaire if eye-rolls and an overdramatic shake of the head were included. 

Last year, when I bought a new pair of bright blue Air Jordans, I was told I was too old for them. Wearing my old NBA jersey (Tim Duncan, Spurs) is considered a mortal sin to them.

Any T-shirt or sweater I buy them ends up in the back of their closet and eventually at Goodwill. While I’ve learned to stop buying them clothes, I’ll never give up my fashion choices. 

Turns out I’m not the only father forced to defend his outfits. Some are stubborn, some do it for laughs, and some think they’ve earned the right in middle age to wear what they want. 

Ken Anthonyknows his Nike Air Monarchs are ugly. His family knows it, too. There’s even a group chat where they discuss his questionable decisions.

When his partner asked him to change shoes before going out, he had a simple answer: “I asked her if she really cared, and she didn’t. I told her my basketball bunion doesn’t either.”

The Monarchs stayed on.

Ken isn’t some guy who’s given up on style. He owns Jordan 3s and 5s. (A fellow shoe enthusiast!) He has other sneakers in his closet he should donate, but can’t bring himself to part with.

But somewhere along the way, Ken’s priorities changed. “The difference now is I put my comfort over my perception,” he told HuffPost. “It’s not that I don’t care what people think, I just care more about how I feel at the end of the day.”

When friends or family make jokes, he owns it. “They’re ugly, I know, but my feet feel amazing.” His philosophy is simple: “Be yourself; everyone else is taken.”

For Scottie Smith, it’s not about comfort. It’s about what he learned growing up. “

I grew up in a time when shorts went below the knee,” Scottie explained. “If your underwear showed underneath, an adult was going to correct that immediately.” He can’t shake that training. His long shorts are “comfortable, familiar, and a quiet protest against trends that would have gotten us in trouble growing up”.

Scottie’s shorts end six inches below the knee. His 15-year-old son’s end six inches above it – they actually measured it. His son isn’t the only one who hates them. At school events and tournaments, Scottie gets looks, groans and jokes.

His boys have started calling him Uncle Drew, the ancient basketball player from Kyrie Irving’s viral sketch. On the very rare occasion Scottie wears shorts above the knee, it becomes “a whole thing and everyone in the family talks about it”.

He’s not changing. “At this point, the longer the shorts, the clearer the message. I’m an ‘old head.’ I’ve earned the right to keep my knees covered, and I’m not trying to relive my youth.”

For some dads, it’s not about comfort or principle. It’s about childhood memories. Steve DiMatteo still wears a tank top from eighth grade. It’s the only shirt that has survived from that era of his life.

“Other shirts just methodically bit the dust,” he said. “And I realised that this one just kept making the cut, and eventually that became a sacred thing, to be the last shirt standing from an old era.” He has a photo of himself in seventh or eighth grade wearing it. Over time, it became sentimental.

His kids point out the ridiculous holes, but Steve isn’t worried. “They’re young enough that I can shape them to be appreciative of this achievement.”

But there’s more to it than nostalgia. It’s become a challenge. “There’s something magical about it now,” Steve said. “I feel like I need to keep testing the limits of the very definition of a shirt at this point. It seems like this will end with me getting kicked out of a public place.”

His favourite reaction came from an old elementary school buddy who also keeps ancient shirts. “You should have seen his eyes light up in appreciation upon learning of this shirt.”

Best friends Mike Lee and Chris Mule have taken it to another level. They wear matching outfits on every vacation. Hot dog prints. Floral patterns. Hugh Hefner-style velvet smoking jackets with satin pyjama pants.

The tradition started on a Virgin Voyages cruise with theme nights. Chris brought matching pyjamas for himself and Mike. It escalated and now they bring matching outfits on every trip.

People have mistaken them for a couple. A bartender once told them a customer said, “What a cute couple! I love that they dress alike for date night.” Another time, a man approached Chris and asked if Mike was his partner.

Mike’s 18-year-old daughter, Jaylen, has a standard response when she sees them getting dressed. “Where are you going dressed like that?” 

Mike and Chris ignore her. They love their loud fashion and refuse to conform for anyone else. As far as they’re concerned, their matching sets are fun and stylish. The louder the pattern, the better.

Nick Caccavo takes a different approach to mortifying his daughters. He shows up to elementary school pickup in a wetsuit. Regularly.

As a small-business owner in the windsports industry, he needs to get on the water for dawn sessions. The water is cold. Sometimes the sessions run long, and the wetsuit takes five minutes to put on and take off. When that happens, he has a choice: see his daughters before school or waste time changing.

The wetsuit wins.

His younger daughter asks, “Why are you wearing your wetsuit, Daddy?” His older daughter delivers the full treatment. “Daddy! You’re sooo embarrassing!” Complete with eye-rolling. 

Other parents don’t say anything to Nick. But they deploy what Nick describes as the “awkward quick look and then pretend I didn’t see that and look elsewhere” strategy.

Asked whether wearing the wetsuit to school is time management or deliberate embarrassment, he said, “Both. Equally. On the mortifying side, it’s pure joy for me.”

Every single one of these guys could change. Ken could wear the Jordans. Scottie could buy shorter shorts. Steve could throw out the tank top. Nick could change out of the wetsuit. Mike and Chris could dress like adults. 

They won’t. 

My line? Bright blue Air Jordans and a Tim Duncan jersey, which my sons think should have been retired along with Tim himself.

Sorry, boys. The jersey stays. Be grateful it isn’t a hot dog outfit.