How To Dress Like A (Cool) Dad

Fashion


fit man with a neat, bushy mustache and glasses, wearing classic fit blue jeans, chunky white sneakers, and a fuzzy, maroon wool sweater

Dad style has been just about everywhere for the past several years. It started with the return of chunky sneakers. Suddenly, we looked down to discover we were all wearing New Balances again. Gradually, it developed into a wider appreciation of old band tees, classic fit blue jeans, ball caps, braided belts, and a whole lot more.

But what exactly is dad style? And how can you nail the look for yourself?

Well, it can be tricky to pinpoint, because dad style is a constantly evolving force of nature. What your dad wears today might not mirror the fatherly uniform of the early 2000s, late 90s, and so on.

To truly understand dad style, its better aspects, and what is worth emulating, simply read on. Or call your dad – afterwards, that is.

Enduring Classics

A great deal of what we now refer to as dad style is really just classic men’s style pieces that have stood the test of time. Wardrobe staples for generations that are reliable, versatile, and practical. Here are a few examples to give you an idea of what we mean:

  • Khakis and Chinos: While originally designed to outfit British troops, khakis have cemented themselves as one of the foundational pieces of any man’s wardrobe – and that especially applies to dads. They’re a lot like blue jeans in that they pretty much go with anything, but with an ounce of more formality.
middle aged man wearing high-waisted, straight-fit pleated khakis
  • The Oxford Shirt: Button-down shirts aren’t always formal, and the oxford shirt is proof that casual can still look incredibly sharp and put together. Their iconic buttoned collar points are a trademark of classically casual style. Crafted from typically thicker, structured, cotton oxford cloth, these shirts pair perfectly with anything – and are especially at home with a reliable pair of khakis or chinos.
button dow collar shirtbutton dow collar shirt
  • Blue Jeans: Possibly the most iconic piece of clothing ever created, dads of decades past did a lot of the legwork to get these denim icons where they are today! The most classic blue jeans are also the ones typically favored by dads, from brands like Levi’s, Wrangler, Lee, and other denim powerhouses.
man with a mustache wearing loose-fitting, blue, bootcut jeans with a white t-shirt and bootsman with a mustache wearing loose-fitting, blue, bootcut jeans with a white t-shirt and boots
  • Chunky Knitwear: The best dads among us favor sweaters with a bit of extra thickness about them. No wimpy, thin merino knits. Think of chunky shetland wools, lambswool fair isle crew necks, fisherman sweaters, cable-knits.
man wearing a thick wool fair isle knit crew neck sweaterman wearing a thick wool fair isle knit crew neck sweater
  • Crew Neck T-Shirts: Until millennials started becoming fathers, you wouldn’t have caught any dad dead wearing a v-neck tee. The way a classic crew-neck hugs the neck just feels incredibly dad-like. Then, once they tucked them into their jeans? That’s a fatherly aura, no question.
classic white crew-neck tee shirtclassic white crew-neck tee shirt
  • Chunky Sneakers: Remember what your old man wore when he used to mow the lawn? Money has it that he was sporting a pair of classic white New Balances. Other classic chunky sneakers might hail from brands like ASICS, Saucony, or HOKA.
chunky white New Balance style sneakerschunky white New Balance style sneakers
  • LoafersWhen dad wasn’t wearing big sneakers, he might have been wearing a knockaround pair of loafers. Loved for their ability to traverse the lands between formal and casual, loafers are an enduring staple of classic men’s style, and hence, dad style.
oxblood leather tassel loafersoxblood leather tassel loafers

Good Dad Style vs Bad Dad Style

A clash of titans, to be sure. But in all honesty, the differentiation between what makes a dad fit good and what makes one bad often comes down to the execution. Pulled off correctly, dad style signals a sense of responsibility, reliability, a dorky charm that you can trust and share a beer with while debating which of The Eagles’ songs is their very best.

Bad dad style? It’s sloppy. Past its prime. Things don’t fit like they did when the old man was in college, and he seems painfully unaware of this fact. Basketball shorts with flip-flops and hockey jersey from college that’s about to burst at the seams. Bad dad style doesn’t age gracefully.

sloppy-looking man in long shorts, an old sports jersey that doesn’t fit, and crocssloppy-looking man in long shorts, an old sports jersey that doesn’t fit, and crocs

Imagine two versions of a dad. One is wearing the lousy outfit described above. Oh, and he uses 5-in1 shampoo/body wash, to really sell the idea that this is a poorly-adjusted man.

The second version of your dad is wearing classic blue jeans by Lee. They’re a bit loose, but they fit him well, secured with a brown braided leather belt. He’s wearing a classic white t-shirt adorned with a tasteful Miller Lite logo. His shoes? Chunky and white. A ball cap celebrating his favorite team. He’s got a great stache, too.

strong, mustached man wearing a white t-shirt with retro blue jeans and big white sneakersstrong, mustached man wearing a white t-shirt with retro blue jeans and big white sneakers

Now think, which dad exudes confidence and responsibility? Which one will be able to teach you how to do your taxes, realistically?

Get what we’re saying? The best dad style is definitely a bit dorky, sure. But it’s also put-together, in its own way. It shows care and commitment. He knows how to dress up just fine too, when the occasion calls for it. He’s not blissfully unaware. His style communicates that he’s got a strong head on his shoulders.

The short version? Always strive for dorky charm over sloppiness.

When Dad Style is Suddenly Cool

handsome middle-aged man at a cafe wearing a blue navy blazer with gold buttons over a white t-shirthandsome middle-aged man at a cafe wearing a blue navy blazer with gold buttons over a white t-shirt

The thing is, dad style can be objectively sharp, too. Dorky charm is, well, charming. But the best dad style indicates that pops knows how to dress up a bit when he needs to. It all comes down to his understanding of the classics, beyond just the most casual types of attire.

Here are a few easy steps and rules worth following.

  • Sure, khakis are involved. But at their best, they’re not just any old pair. They’re full-fitting through the leg and the seat, giving the legs room to breathe. They sit higher on the waist, elongating the leg profile. They might even have a couple of pleats, to add visual depth and perhaps some extra space for thicker thighs.
man wearing high-waisted, pleated khakisman wearing high-waisted, pleated khakis
  • Those oxford shirts we mentioned before? Trust us, styled properly, they can look plenty cool. Again, fit is key here. The ideal oxford shirt is on the thicker side, and not terribly tight-fitting. If anything, it should be ever so slightly loose! Tucked in and with the sleeves rolled up, it creates the perfect masculine silhouette. Wearing a ribbed tank top undershirt? Pop a few buttons to expose it for extra burly dad points.
masculine man in an oxford cloth button down shirt worn over a ribbed tank top, with a few buttons on top openmasculine man in an oxford cloth button down shirt worn over a ribbed tank top, with a few buttons on top open
matching brown leather loafers, braided brown leather belt, and brown leather watchmatching brown leather loafers, braided brown leather belt, and brown leather watch
  • Heading to dinner? The versatility of this particular fatherly uniform allows it to be dressed up with total ease. All you need is a classic sport coat or blazer and you’re good to go. Go for an iconic navy blazer with gold buttons for a dash of preppiness, or perhaps a tweed sport coat to get some extra texture mileage.
handsome man wearing a green tweed sport coat over a brown oxford shirthandsome man wearing a green tweed sport coat over a brown oxford shirt

Cool dads get that classic style never goes out of, well, style.

That’s why they commit to wearing foundational pieces that fit them well and work for a variety of situations. Casually, they refuse to look sloppy. Formally, they know what good tailoring is. In-between? They combine the two effortlessly.

Where to Shop for Dad Style Staples

So, you want to try it out for yourself? We don’t blame you. There’s something special about this whole genre. It’s like a soft-spin on classic menswear, but not so stuffy that it doesn’t permit you to break out shorts and a tee. But those shorts will be glorious, no doubt about it.

Here’s where to shop to get your hands on some wardrobe classics, and to find even more style inspiration.

  • J.Crew: The kings of mall-prep and more recently, a return to their signature looks. Their current offerings are filled to the brim with dad-core pieces at a solid value, especially if you shop their frequent sales.
J.Crew logoJ.Crew logo
  • Brooks Brothers: The granddaddy of American tailoring still has a ton to offer for slightly more sophisticated dad-inspired looks. Their oxford shirts won’t fail you, and they’re a good shout for some solid blazers, as well.
Brooks Brothers logoBrooks Brothers logo
  • New Balance: The king of iconic chunky sneakers, they currently offer a ton of fashion-forward options within the lifestyle and running shoe categories. Our tip? Go for something neutral, in white, gray, or beige, for maximum versatility. Their limited Made in the USA line will make your old man proud, too.
New Balance logoNew Balance logo
  • Ralph Lauren: If you want some of the best, most timeless pieces currently available on the market, head to Ralph. From great khakis to excellent oxford shirts, not to mention spectacular knitwear and tailoring, Ralph Lauren is a shortcut to enduring dad style with a dash of elegance.
Ralph Lauren is a perfect brand for dad styleRalph Lauren is a perfect brand for dad style
  • G.H. Bass: One of the best options for a wide range of loafers, you can count on G.H. Bass for quality. If you’re feeling even more adventurous, they offer some killer lug-soled boat shoes, too. Now that’s hardcore dad-mode.
G.H. Bass logoG.H. Bass logo
  • Wrangler: With some of the best value jeans available, you can’t go wrong with Wranglers. Their Cowboy Cut jeans are especially popular, and with their slightly higher rise, absolutely scream dad vibes. In the best way, of course.
Wrangler LogoWrangler Logo
  • Levi’s: Possibly the most iconic denim brand of all time, Levi’s is favored by just about everyone, and that includes stylish dads. Their 501s are timeless, but if you want our expert advice, go for their 501 ‘93 Straight Fit jeans for a slightly more retro look that your own dad very well may have worn himself.
Levi’s LogoLevi’s Logo
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Dad Style Endures

From icons like Tom Selleck to Billy Crystal, dad-core has been at the center of attention for longer than you’d think. It just took a bit for everyone to put a name on it.

While at its core, dad style is just about wearing classic pieces well, it’s also about standing firmly in the camp of good taste, exuding a sense of reliability and confidence.

Dad style can be dressed up. It can be dressed down. But it will always be an excellent source of style inspiration, no matter the occasion.





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