Perfect Pairings | Dad Hats & Dapper Button Downs

Are street style designers paying homage to the most important man in their lives? Maybe. Or perhaps an old favorite silhouette is just coming back in a big way. While Pops may very well be the best friend of the guys and girls behind some of our favorite brands, we’re betting that these caps, that go by the name “Dad Hats”, have taken over for another reason.

The big flat brims are great, as are snapbacks, but when you’re looking for something a little more understated, we suggest this more fitted and curved brim version that can squish up and fit in your back pocket. What to wear them with? Well, just about anything. But to make the class-act look a little more lived-in, pair them with a short-sleeved, collared, freshly ironed button-down. We have some recommendations. 

Don’t Get Faded

dad hats

Photo: Dad Hat by Faded Royalty; Button-Down by Saturdays NYC.

Don’t get faded; you know Dad never would. Dads always keep their composure, even after throwing back a few, or a case, of PBRs. Mix cool with classy by sporting a worn-in looking Dad hat, paired with a proper, though slightly kooky, button down. Try the Faded Royalty, Wolf Denim Dad Hat, $32, paired with the Saturdays NYC, Esquina Maze Shirt, $135.

Peach Punch

dad hats

Photo: Dad Hat by Huf; Button-Down by Barney Cools.

Dads don’t fight, but that doesn’t mean they can’t pack a mean (style) punch. Pairing colors in the same rose-colored family creates a low-key, uber stylish vibe. These two are so perfectly similar yet strikingly different from one another that wearing them together is unexpected perfection. Partner the Huf, Script Curved Brim 6-Panel, $32, with the Barney Cools, Excursion SS Vintage Red, $89.

The Night Life

dad hats

Photo: Dad Hat by Rad is Rad; Button-Down by Scotch & Soda.

The Dad hat gets an endearing treatment with a throwback reference. 143, or for anyone born in the age of smartphones, ‘I love you’, from back in the olden days when conversations depended on moving your thumbs as fast as they could go across 12 physical buttons on your flip phone. Wear the cheeky Rad is Rad, 143 Dad Hat in Black, $24.99, with the dapper Scotch & Soda, Short Sleeved Shirt in Dessin C, $109, which features black screenprint on a dark chambray shirt. 


dad hats

Photo: Dad Hat by The Hundreds; Button-Down by Globe.

Ideally, at some point, we see The Hundreds, Rose Dad Hat, $36, out on the golf course. While this cap could pass for something regularly worn with a white polo & tan khakis, we know the truth – and it’s really a well-fitted, unexpected style from a street style legend. When you head out to the Hole No. 1, we recommend doing so in this hat, and the Globe, Mains Shirt, $59.95. Try blending in by tucking it into some pleated shorts. Or don’t. 

Periwinkle Twinkle

dad hats

Photo: Dad Hat by Stussy; Button-Down by Frank & Oak.

The best Dad hats are aged to look like they’ve been around as long as your relationship with your pops. The Stussy Stock Low Profile Strapback, $35, fits the bill, shown in a washed out periwinkle, but also available in black, pastel pink or white. Pair it with the unique Frank & Oak, Bermuda Triangle Printed-Sleeve Shirt, $56, which features navy all over print sleeves, on a crisp white body.