Look Like a Dad Boss 10 Stylish Outfits Youll Want to Steal From Your Dad

There’s long been a myth that coolness and fatherhood are not capable of coexisting, that, when it comes to clothes, dads are preternaturally drawn to sloppy fits and unnecessary bulk. And yet dad fashion has simultaneously been on trend for a few years now, as chunky New Balances and light-wash, high-waisted jeans have become increasingly ubiquitous among young people who manage to look chic and coolly ironic in the very same clothes that have traditionally made dads look anything but. So what’s a dad to do and more importantly, how’s a dad supposed to dress?

So how does a dad manage to strike the perfect balance there? To remain at least somewhat on trend while neither looking like he thinks he’s still 22 nor like he’s fully given himself over to bad dad style?

Well, we’ve got to start by dispeling the notion that dads can’t be cool, and then it’s time to look toward the fashion of dads who continue to express themselves stylistically. Below are five cool dads who are rewriting the rules for how men can and should dress after becoming parents.

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Matty Matheson has amassed a wealth of devoted fans in recent years, not simply for his cooking skills and outsized personality but his personal style, too. The heavily tattooed chef and father of three has established a dress code for himself, a uniform that subtly varies from day to day but ultimately consists of the same base pieces —t-shirts, jeans, a pair of clog-like shoes that lend themselves well to the lifestyle of a chef, all topped off with some type of hat. It sounds simple enough, but the key to Matheson’s style, and what makes it so interesting, is his penchant for workwear-inspired pieces and vintage tees, the former of which offer details like patch pockets and the latter of which are typically thrashed within an inch of their life. When paired with Birkenstock Bostons or the Yeezy-esque Merrell water shoes, plus a retro trucker hat or beanie perched slightly atop the head, it’s a look that emanates an effortless cool that many go to great lengths to try and achieve.

Like Matheson, actor Adam Pally, also a father to three, gravitates toward workwear styles and brands, whether it’s a heavy-duty canvas jacket or Red Wing boots. But the actor isn’t afraid to occasionally throw some hypebeast elements into the mix, typically in the form of a highly-enviable pair of sneakers. For the dads that have always been curious about Jordans but felt they didn’t have what it takes to pull them off, Pally demonstrates how to wear them without looking like a poser, pairing them with practical pieces like jeans or chinos and a classic blue oxford, a look that’s achievable without being boring. Never leaning too far in any stylistic direction, it’s evident that Pally simply abides by the rule of wearing what he likes, making the pieces work to fit into the confines of his own personal style, whether that means pairing Wallabees with a minimalistic suit or Air Jordan 1s with a blazer. We also commend his recent decision to bleach his hair at 39.

Of cool dads. Having previously modeled for the likes of Supreme and Burberry, McCoy is currently creative director at Thames, largely inspired by skatewear and British culture, in addition to holding the important title of father. Long lauded for his personal style, McCoy really seems to have come into his own in recent years, his manner of dressing no doubt influenced by fatherhood. Still keeping the occasional boyish elements like knee socks worn with shorts and Addias trainers, his style is infused with classic menswear pieces like crisp striped button-downs and navy crewnecks, pieces that are styled in reflection of his youth (he is only 24 after all) and background, the addition of a heavy gold bracelet and chunky rings or a pair of sleek rectangular shades making them feel fresh again.For all those classic menswear pieces you have lurking in your closet but are loathe to wear because they feel overdone, McCoy’s style is a masterclass in reinvention.

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The fact that Adonis Bosso is one of the most sought-after male models certainly doesn’t hurt when it comes to his coolness factor, but that’s not what solely makes him cool, especially when you learn he frequently dons matching outfits with son Saphir, outfitting him in mini leather jackets and sweatsuits that mirror his own. When he’s not matching his son, Bosso takes a laidback approach to dressing, which is understandable given the more ostentatious designer pieces he has to wear for a living. This isn’t to say Bosso’s style is lacking interesting elements, as he frequently gleans inspiration from his African heritage, and he isn’t afraid to throw vintage pieces into the mix, like a Harley Davidson leather vest worn over a Bob Marley tee with a fuzzy houndstooth jacket and a cowrie shell dangling from his hair.

Mordechai Rubenstein, known by most as Mister Mort, has long been highlighting other people’s style, but it’s time we give him the recognition he deserves for his own. A frequent fan of gorpcore pieces (think L.L.Bean pull-overs, Birkenstocks and hiking roots) Rubenstein incorporates the pieces with his other preferred wardrobe essentials — oxford shirts, patterned ties, colorful berets and corduroy pants. The result is an often a colorful amalgamation of clothing that only someone with Rubenstein’s expert hand at styling could pull off, the seemingly disparate colors making sense as he layers a pink v-neck sweater over an olive collared shirt (with the collar popped, of course) paired with ’90s jorts and Birks. It’s style part preppy, part granola, part yuppie, part Deadhead and definitely kooky, but it’s never boring.“Hey dad, can I borrow your jeans?” said no child, ever, in the history of the universe. Well, at least until sometime around 2018. Since then, the average Middle-American father has become something of a style icon.

A natural successor to normcore’s function-over-form aesthetic, so-called ‘dadcore’ is an anti-fashion subgenre of menswear that favours comfy over ‘cool’, and would sooner enjoy a crisp light beer with the guys than expend valuable grilling energy trying to keep up with the latest trends.

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The first signs of a shift came in the mid-to-late 2010s, when your old man’s go-to lawn-mowing shoe, the New Balance 990, came back into focus. Since then, pops’ entire wardrobe has been co-opted by the younger generation, with everything from ill-fitting (but comfortable) denim to socks and sandals entering the conversation. And that’s just the tip of the iceberg.

So, which other items should you be raiding your dad’s wardrobe for? Below we’ve highlighted a few of the key pieces that underpin this easy-going sartorial movement, covering everything from wraparound Oakleys to fuzzy fleece jackets and beyond.

‘Dad caps’, as they’ve come to be known colloquially, are simple cotton sports caps that lack the rigid front panels often found in traditional fitted baseball caps. They’re low-profile, soft and often come emblazoned with a logo, motif or sports-team emblem of some sort.

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More often than not, the adjustment strap at the back is made from the same cotton fabric, or occasionally leather, which further differentiates them from other styles, like trucker hats and snapbacks. We love them because they’re fuss-free, easy to wear and tend to look even better when they’re a bit weathered.

It’s hard to beat a fleece when it comes to a cosy midlayer. Comfy and insulating, these practical jackets are ideal for fall and winter, either layered under a coat or worn on their own on milder days. The textured face fabric is great for giving cold-weather looks a bit of character, particularly when you opt for a heavy, thick-pile version.

For some of the best, check out Patagonia’s Synchilla Snap-T and Retro-X models – two iconic garments which feature a thick micropile fabric and heavyweight deep-pile fleece respectively, and are among some of the most coveted items on the vintage market.

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Legwear doesn’t come much more practical than a good pair of cargo pants. Once vilified by the menswear community, these dad-friendly trousers are now en vogue, with everyone from cutting-edge streetwear brands to high-fashion labels making their own versions.

They go great with loose-fitting pieces and laid-back casualwear, but be wary of teaming them with similarly heavily pocketed outerwear, unless of course you’re deliberately going for the Engineered Garments look.

The emergence of so-called ‘dad shoes’ as a footwear trend is symptomatic of fashion’s pivot away from slim silhouettes and towards bigger, bulkier shapes. This has been going on for years now, but while time might be running out for wide-leg trousers and chunky sneakers like Balenciaga’s Triple S, these understated, oversized kicks are seemingly here for the long haul.

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If you’re looking for a good example, check out New Balance’s 990 line, which epitomises the dad-shoe look. Essentially, these are sneakers designed with comfort at the fore, and the fact that they’re actually super versatile and easy to style is just a nice bonus.

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