Does Anyone Ever Regret Joke Outfits for Special Occasions?

I was checking my Facebook feed when I come across a photo of a young couple who were going to homecoming. As I get older, young people only look younger, and I think they’re high schoolers rather than college. The kid wanted to wear a Rick & Morty tie but couldn’t fine one, so his mom bought a black tie and painted Rick & Morty on it for him and it looks pretty good.

I don’t personally have strong feelings one way or the other in regards to how someone chooses to dress for some social occasions. If someone wants to wear a tuxedo t-shirt to prom, well, more power to ‘em. On those rare occasions when someone looks back at a joke outfit they wore to a serious occasion, do they ever regret their choices? I’ve certainly laughed at some of the outfits and styles from my youth, but I can’t say I’ve ever regretted what I chose to wear when it came to formal events.

I’d hardly call a tie with a cartoon character on it as a “joke outfit.”

For a formal occasion I can’t help but think of it as a joke article of clothing at least.

I don’t regret not setting foot in stuffy formal occasions.

My son wore a chainmail tie to a formal wedding recently, and it was a huge hit. Turns out the other groom (not the one who invited us) makes chainmail, and loved it.

Anyway, my guess is that the sort of person who wears a joke outfit to a formal occasion is generally happy with the outcome.

I wore a tuxedo t-shirt, not to prom, but to our state fair as a member of a small pep band that roamed the grounds in the 1970s, playing our school fight song, which was well received by alumna there. I’m pretty sure we never asked for permission, we’d just find a spot or take over the beer hall for a mini-concert. We were supposed to dress as a bum, but back then the tuxedo t-shirt was just gaining popularity, and were hard to find. So I just took a magic marker to a white t-shirt, drawing on a tuxedo. It was fine, until I got home after a long day and saw myself in a mirror for the first time. As I sweated in the heat, the magic marker had ran and streaked all over. Nobody said anything all day.

When I think of a ‘joke outfit’ for prom, I’m thinking of something more along the lines of a duct tape tux:

Yeah, as a guy who has appeared in numerous absurd and creative outfits…. I mean, I did a Jews Harp solo wearing nothing but a large moustache, cowbow boots and rhinestone spangled g-string, that tie is pretty tame.

(It was for a fundraiser for our camp at Afrika Burn, an offshoot of Burning Man, so weird is fairly normal)

Homecoming is not an actual “formal occasion.” It’s kids going to a dance.

A college friend of mine got married on the pirate ship outside Treasure Island Casino in Vegas. My invitation got lost in the mail, so I wasn’t able to attend. The bridal party was dressed in pirate attire, and guests were invited to do the same. I absolutely 100% would have rented a Pittsburgh Pirates uniform to wear, and there’s not a day goes by that I don’t regret having missed that opportunity.

I think any event with kids isn’t really formal, if a high school dance isn’t a good time for playful wardrobe, when is?

NSW Premier Dominic Perrottet wore a Nazi uniform to his 21st birthday party. He revealed this after a colleague raised it with him. I would imagine that, since the article mentions Prince Harry being photographed in a Nazi uniform with a swastika armband, it was a fairly common thing for those that could afford a costume.

My wife’s sister got married at the Jersey shore aboard ship, and it was suggested that everyone dress like Pirates for the occasion. So I did – I had a pretty good and complete pirate costume I’d put together for Halloween a few years previous. So I got there, dressed as a pirate, braided beard, eyepatch, and all (but no peg leg or hook hand – there’s a limit). And found that I was the only one who dared show up in costume.

I’m not sure I regret it. You feel a certain freedom when you’re in costume.

Of course you wouldn’t regret it. Given you were encouraged to dress that way, your outfit was entirely appropriate. I wouldn’t normally wear shorts and a Hawaiian shirt to a wedding, but the invitation encouraged me to dress in that manner and so I was happy to oblige.

A character on a long-forgotten TV show in the 70s wore a red suit, and it got comments. So I thought I needed one. I could wear it and make an impression! People would comment! The best we could find was a red sports jacket. The reality of wearing it didn’t match my visions, so it went to the back of the closet and eventually away. So I regret spending good money we didn’t have on something that really wasn’t a good idea. I was 10.