Style Inspo: How to Dress Like a (Cool) Dad

Over the past few years, dad style has become almost ubiquitous. It all started with the return of chunky sneakers. Suddenly, we looked down and realized we were all wearing New Balance again. Gradually, it developed into a broader appreciation for vintage band T-shirts, classic-fit blue jeans, baseball caps, woven belts, and more.

But what exactly is dad style? How to create the perfect look for yourself?

Well, pinpointing it can be difficult because dad style is a force of nature that is constantly evolving. What your dad wears today may be different from the dad uniform of the early 2000s, late 90s, etc.

To truly understand dad style, its benefits, and what's worth emulating, read on. Or call your dad—afterward, that is.

Enduring Classics

What we now call “dad style” is really just classic men’s style pieces that have stood the test of time. Reliable, versatile and practical, a wardrobe staple for generations. Here are some examples to give you an idea of what we mean:

• Khakis and Chinos: Although khakis were originally designed for the British Army, they have now become one of the basics of a man's wardrobe—especially for dads. Much like blue jeans, they go with just about anything, but with an added touch of formality.

• Oxford Shirt: A button-down shirt isn't always formal, and the Oxford shirt proves that casual clothing can still look incredibly sharp and put together. Its signature button-down collar is a signature of classic casual style. Crafted from a typically thicker, structured cotton oxford, these shirts pair well with anything, but especially pair with your trusty khakis or chinos.

• Blue Jeans: Possibly the most iconic garment of all time, dads decades ago did a lot of legwork to make these jeans what they are today! The most classic blue jeans are also the favorite jeans for dads and come from denim brands like Levi's, Wrangler, Lee and more.

• Chunky Knits: The best dads among us love sweaters that are a little chunkier. No flimsy, thin merino wool knits. Think thick Shetland wool, Fair Isle lamb crewnecks, fisherman sweaters, and cable knits.

• Crew Neck T-Shirts: Until Millennials start becoming dads, you won’t see any dads dying in V-neck T-shirts. The way the classic crew neck hugs the neck feels very dad-like. And then, once they tuck them into their jeans? There is no doubt that this is the breath of fatherly love.

• Thick-Soled Sneakers: Remember what your old man wore when he mowed the lawn? He reportedly wore a pair of classic white New Balance shoes. Other classic platform sneakers might come from brands like ASICS, Saucony, or HOKA.

• Loafers: When Dad isn't wearing big sneakers, he's probably rocking a pair of eye-catching loafers. Loved for their ability to go between formal and casual, loafers are a timeless staple of classic men's style, and therefore a must-have for dad style.

Good Dad Style vs. Bad Dad Style

One thing is for sure, this is a Clash of Titans. But let’s be honest, the difference between good and bad dads often comes down to execution. Done right, dad style signifies a sense of responsibility, reliability and a goofy charm you can trust to share a beer with you while debating which Eagles song is their best.

Dad's bad style? This is sloppy. Past its prime. Things are different than they were when the old man was in college, and he seems painfully unaware of this fact. Basketball shorts paired with flip-flops and a college hockey jersey that’s about to burst at the seams. Bad dad style doesn’t age gracefully.

Imagine two versions of your father. One of them was wearing the terrible clothes described above. Oh, and he also uses 5-in-1 shampoo/body wash to really sell the idea that this is a poorly adjusted man.

A second version of your dad wears classic blue jeans from Lee. They are a bit baggy but fit well and are secured with a brown braided strap. He wore a classic white T-shirt emblazoned with the tasteful Miller Lite logo. His shoes? Thick and white. A ball cap celebrating his favorite team. He also had a great performance.

Now think about it, which dad exudes confidence and responsibility? Who can actually teach you how to file your taxes?

Do you understand what we are saying? Of course, the best dad style is a little silly. But it also comes together in its own way. It shows care and commitment. He also knew how to dress up when the occasion called for it. He wasn't blissfully unaware. His style shows that he has a strong mind.

The short version? Always go for silly charm rather than sloppiness.

When Dad Style Suddenly Becomes Cool

The thing is, objectively speaking, dad style can also be edgy. Silly charm is charming indeed. But the best dad style shows that dad knows how to dress up when the occasion calls for it. It all comes down to his take on classics, not just the most casual types of clothing.

Here are some simple steps and rules worth following.

• Of course, khakis are also involved. But at their best, they were more than just an old duo. They conform perfectly to the legs and seat, giving the legs room to breathe. They sit higher on the waist and elongate the silhouette of the leg. They may even have a few pleats to add visual depth and perhaps provide some extra room for thicker thighs.

• Those Oxford shirts we mentioned earlier? Trust us, they look cool if styled right. Again, fit is key here. The ideal Oxford shirt is on the thicker side and not too tight. If anything, it should be slightly looser! Tuck in and roll up the sleeves for a perfectly masculine silhouette. Wearing a ribbed tank top? Pop a few buttons to expose them for extra burly dad points.

• Add a pair of full-grain leather loafers. The fringed ones are especially fun and look great with matching belts and straps.

• Going to have dinner? The versatility of this special dad uniform makes it easy to dress up. All you need is a classic sport coat or blazer and you're good to go. Choose a signature navy blazer with gold buttons for a hint of preppy style, or opt for a tweed blazer for an extra touch of texture.

Cool dads agree that classic style never goes out of style.

That’s why they aim to wear basic pieces that work for them and are suitable for every occasion. Casually, they refuse to look sloppy. Formally speaking, they know what good tailoring is. Somewhere in between? They combine the two effortlessly.