They Don’t Call Them Fun Shirts For Nothing

Flat-lay of a Rowing Blazers fun shirt
Image is my own / All rights reserved

Menswear, at times, can feel a little too serious. Too Stuffy. Reserved. Buttoned-up, if you will. 

A level of obsession over rules, tradition, and tiny details in some quarters can be stifling; all of the insider know-how and flaunting of expertise can get a little exhausting. 

You might be tempted to look across the fence at what seems to be a glorious anything-goes ethos in women’s clothing and feel green with envy over their more verdant, vestiary pastures. 

It’s especially tempting to feel this way about classic menswear. However, from within this selfsame tradition, with all of its sartorial shibboleths and IYKYK cleverness, there has long existed a concurrent thread that embraces, well, to put it simply: Fun!

I’m thinking here of clothing that’s colourful, eye-catching, even a little silly. This kind of thing might feel like a contemporary phenomenon but an embrace of the fun side of men’s clothing has been around for a long time. Think of well-established trends like Nantucket Reds, two-tone shoes, bold-patterned ties, and light-coloured socks. Or, my personal favourite: the appropriately-named ‘fun shirt’.

The fun shirt — which is to say a shirt (historically a button-down) combining multiple blocks of fabric featuring different colours and patterns — was a Frankenstein’s monster brought to life by a somewhat unlikely creator. This giddy, fanciful, eye-catcher of a garment came into being in the 1970s on the factory floor of that most blue-blooded and respectable purveyor of American menswear, Brooks Brothers. 

As the legend goes, while on a visit to one of his company’s shirt factories, Ash Wall, the great-great-great-grandson of Brooks Brothers founder Henry Sand Brooks and vice president of the company at the time, caught sight of some discarded practice shirts. These had been cobbled together from mismatched bits of left-over cloth by shirtmakers looking to perfect their sewing technique. He is said to have picked one up off the assembly line, tried it on right on the spot and declared: ‘These are some fun shirts.’

The name stuck. As did the design, despite various factory workers’ apparent attempts to dissuade Wall from wearing his new discovery, since it was an imprecise training garment and therefore not fit for wear. One imagines (like many sceptics who have looked upon fun shirts since) that they might also not have been quite as taken with the aesthetic as Wall was. Nevertheless, the BB VP could not be dissuaded and soon the company started selling these colourful patchwork numbers in their stores and continued doing so throughout the ’70s and ’80s.

Fun shirt in a Brooks Brothers window
Image credit: Elvert Barnes / CC BY-SA 2.0

Fun shirts duly delighted like-minded Brooks customers and soon filtered into the fringes of popular culture. Geoffrey Blake wears one in Contact, for example. There’s also a photo of a Grumpy Old Men-era Walter Matthau donning one next to Jack Lemmon. More recently (though set in the same period) Jonah Hill’s sleazebag prep character in The Wolf of Wall Street does the same. 

The fun shirt’s original tenure on Brooks Brothers’ production line was sadly short-lived, however, leading many fun shirt aficionados to the far reaches of eBay and Etsy, not to mention any number of beleaguered vintage dealers and thrift stores, in search of their quirky button-downs of choice. 

Luckily, a revival of enthusiasm for all things classic menswear over the last decade or more — including an interest in its odd-ball chapters and lesser-known footnotes — has meant that various brands have brought them back, including Ralph Lauren, J.Crew, J. Press, Drake’s, Rowing Blazers, Beams Plus, Bryceland’s, Jake’s, and, of course, Brooks Brothers themselves.

This flurry of contemporary fun shirts has come in an appropriately dizzying array of shapes and styles and has even inspired the likes of fun shorts, fun PJs, fun hats, and the like. It’s also meant that fun shirts have been worn in all kinds of creative ways and in doing so have proven themselves to be unexpectedly versatile. Casual summer attire has long been the standard approach, but in recent times these jolly tops have regularly been paired up with some very respectable-looking tailoring and nevertheless held their own nicely. Turns out the right fun shirt with a good jacket or a casual suit doesn’t look at all out of place. It shouldn’t work, but it does.

Man wearing a Rowing Blazers fun shirt
Image is my own / All rights reserved

And therein lies the appeal of these silly shirts. They both make sense (in that mentally they clearly slot into the category of ‘shirt’) and don’t (since we hardly expect shirts, or any other clothes for that matter, to look the way they do). They are incongruous, a little gaudy, and they don’t take themselves too seriously, which might make them the perfect garment to describe the prevailing direction much of menswear seems to be taking, in contrast to the often dour-seeming past sketched above.

It feels like no accident that fun shirts have made a roaring comeback in recent times, periodically selling out before being restocked or taken on by some new enterprising outlet. And I’m not just talking here about the arrival of summer and a touch of holiday spirit.

Back in 2020, Aleks Cvetkovic sang the praises of wearing fun shirts at the height of the pandemic. He wrote about there being ‘few garments [that] are a more welcome distraction or more enjoyable to wear in our current malaise than the “fun shirt”.’ He goes on to talk about the psychological benefits of getting dressed in the morning in the context of stress, isolation, and a general overload of everything that’s going on in the world. He ends the piece by suggesting that ‘we can all do with a little bit of fun in our wardrobes right now.’ 

It’s a sentiment that, if anything, has only grown truer in the intervening months and years. So do yourself a favour and consider putting on a button-down that isn’t quite so buttoned-down. Life’s too short not to have a little fun.