Written by Ivan Yaskey in Trends on the 15th August 2018

Dress practically in travel, they say. After all, you’ll just be waiting in line or sitting down. Most might put on some sweats or joggers and have a backpack available. For the normally sartorially savvy Chris Pine, on the other hand, that recommendation returned as overalls. The Star Trek star has been spotted wearing this body-covering garment on multiple occasions over the past two years. On a more recent outing, he allegedly used the bib pocket to hold onto his passport and travel documents. But, Pine’s pragmatic approach exemplifies one menswear conundrum: Overalls might appear on the runways, and be available through workwear brands, but should anyone actually be wearing them as a casual, non-utilitarian style? The answer, unfortunately, isn’t a “yes” or “no”. It’s more a “Maybe – but be careful.”

Overalls emerged sometime in the 18th century as a one-piece item for working men. Initial models didn’t have the bib portion; rather, they resembled denim trousers with buttoned suspenders attached. Because of their durability and practicality, the trend caught on, and by 1873, Levi Strauss started mass-producing them. In 1911, Harry David Lee introduced the first true bib overalls. Sold under the name 'Union-Alls,' they attached the trouser portion to a bibbed shirt with straps. Today, however, especially with multiple pockets and cuffed sleeves, it’s actually closer in design to the coverall. So, considering first its multi-decade history as a working man’s garment, their decades-long use as casualwear, and recent runway resurgence, how should you go about wearing overalls?

Approach Carefully 

It takes the most careful man to handle certain trends – neon yellow, colourfully printed suits, and bum bags, to name a few at the moment. Overalls fall within these parameters, but not for their boldness. Rather, you’ve got to know how to step around their past connotations. In more recent memory, that’s the ‘90s – the last time anyone wore this garment beyond its ironic factor. Tupac Shakur, particularly, gave their pragmatic design a sense of rugged toughness. Will Smith, then on Fresh Prince of Bell-Air, made them seem like a playful, jangly garment, especially when worn with one strap off and a colourful, oversized shirt underneath. As another mimicked, hip-hop rooted trend, Kris Kross turned them around, wearing the crossed back right in front, like a pair of oddly-constructed bondage trousers. For decades before, overalls were synonymous with the working man, whether he toiled away in a factory, grew crops on a farm, or helped build railroads across the American landscape. Because of this history, the garment in certain social circles is still associated with the working man, especially when it’s a functional design from Carhartt or Dickies. But, through this lens, it’s too easy to cross over from appreciative, reminiscent Americana and into hardcore hillbilly territory. As a hint, avoid the flannel shirt or wearing overalls strictly as a jumpsuit, with nothing underneath.

Be Classic  

With these things out of the way, there’s one historical aspect to focus on. Overalls’ classic nature, as a fully denim garment, often with pockets in front, expresses one clear sentiment: You’re there to get things done, with no bells and whistles needed. So, if you’re thinking about trying out overalls, going back to basics is truly the best approach – no irony, no Halloween costume getups, and no dated references. View it through an Americana lens, but without all of that wistful, overly nostalgic context. Instead, be practical: just denim, in a solid shade, ideally mid-wash to dark. For inspiration, turn to the styles Dickies and Carhartt have on the market. By this, we mean a wider fit, rather than a skinny cut, and consider a pocket or two, purely for practicality. By day, however, Carhartt’s cotton duck is too orangey-brown, so be sure to stick with more of a timeless look. As one trend to avoid, the short overall – shortened down to 'shortalls' – can go in two directions. One, it’s reminiscent of something you’d put on a toddler, or any young child that’s graduated past a onesie. Secondly, the shorter length, especially on a grown man, looks suspiciously like a romper. Although two-pieces are having their moment, there needs to be some degree of separation and structure.

Everything Else  

So, once you’ve gotten the fit and material down, you’ve got to think about everything else – especially what you wear underneath. To get out of that ‘90s relic-farmhand dichotomy, avoid a few garments. Anything plaid, including a button-down, appears like you’ve been out in the woods chopping down trees all day. A loud print? You’re trying too hard to relive a cheesy ‘90s TV show. A mock neck top or a sweater? Too bulky, and it’s clear you’re trying to hide something. T-shirts end up being the best solution, although a solid-colour, short-sleeve button-up shirt takes a close second. Because overalls are a tricky statement piece, you’ve got to keep everything else understated and neutral. As such, think a plain white tee, perhaps with a graphic, or a neutral-blue oxford. Chambray, however, ends up seeming like mismatched denim – or a Canadian tuxedo gone wrong. Aside from your shirt, consider layering, with a hoodie or bomber on top. Because overalls tend to look a bit bulky, make sure your jacket isn’t as slouchy, and keep it at the hips. For a workwear-inspired look, try it with a shacket or a solid-colour quilted bomber.

Should a Man Ever Wear Overalls? #style

— Menswear Style (@MenswearStyle) August 15, 2018

Made famous by Kris Kross and also known as Shortalls, Coveralls and Union-Alls, we discuss whether men should ever wear overalls.