How to wear a ball cap the old school way, featuring DJ Jazzy Jeff [The League]

The League of Extraordinary Bloggers have struck again with this week’s assignment:

Write a step-by-step guide on how to do something. This could be a real world project or a fantastical one, so do with it as you will.

Considering my other league posts were rooted in imagination, I’m going to take the real world practical approach with this one. Allow me to play the old man on the porch telling you rascals to get offa his lawn for a minute and mention that I’ve noticed something wrong with the way these youngsters wear their hats nowadays.

Take a look at this and tell me what’s wrong with this photo?

Mark this date down… the ONLY time you’ll ever see Wiz Khalifa on this website…

Other than the obvious, my biggest gripe about it is YO, WHASSUP WITH YOUR HAT, SON?!!

Are you a part-time 18-wheel big rig trucker on the weekends? Did you just get drafted and had to shake hands with David Stern when you got that cap? If your answer to both of those questions is no, then you have no excuse for this kind of behavior.

Unless you just got selected in the first round, the bill of your hat shouldn’t be as flat as Paris Hilton’s backside…

IN MY DAY, there was a universally acceptable method for donning a ball cap. (*Note: Also in my day, snap-backs were still cool, but now it’s all about the fitteds from what these young bucks tell me.) Where did these kids lose their way?

Well, with the help of hip hop pioneer DJ Jazzy Jeff, we’re gonna show you how to properly wear a ball cap, circa 1992:

How to wear a ball cap the old school way

featuring DJ Jazzy Jeff in a 1992 Starter ad

Click to play the video below and read on!

1. First you grab the hat

Easy enough, right? Let’s move on…

2. Then you GRIP the hat

VERY IMPORTANT STEP HERE! You don’t just grab a hat fresh out of your Foot Locker bag and put it on. What are you, raised by wolves? No, sir/ma’am, put a nice grip on the bill of that cap! Take each hand and put it on either side of the front edge of the brim and bend it downward ever so slightly. Repeat a few times, make a nice curved arc of that brim!

3. Then you flip the hat

Most memorable aspect of bartending school that I recall (don’t laugh, best $150 I ever borrowed from my brother that summer!) was the instructor giving us this pearl of wisdom:

“You know how they do all that dancing around and flipping and tossing of bottles in the movie ‘Cocktail‘ with Tom Cruise? Well that’s BULLSHIT, we’re gonna teach you how to make drinks here!”

Same applies to this step– do it if you wanna be flashy, but not important.

4. Make sure it’s a Starter Hat

Remember, folks… this was 1992. EVERY hat was a Starter Hat back then. Plus, it’s their ad, so….

5. Then you graze the hat

Again, you’re not just slapping a cap on your dome, you want to lightly touch the bottom back of the cap against the back of your skull, all while raising the front bill high in the air. This positions the hat high above your head so that by the next step it’s a nice fluid motion…

6. Then you SLAM the hat

While in said grazing position, SLAM, not pull, the entire hat down brim first. The entire cap should easily cover your crown, making for a nice fit. Apologies to any big-headed readers like Bonk, Waynehead or TJ Kidd– you’re all free to skip this step…

7. Then you twist the hat, Then you turn the hat, then you spin the hat

These three steps are combined into one because really they serve the same purpose. As the hat is comfortably slammed onto your head, twist to one side, then turn the other way, then perform a full 360 degree spin of the hat while on your head and stop with your brim front and center (or slightly tilted to the side, however you prefer). This creates a vortex of kinetic energy and centrifugal air flow that allows for maximum fittage of the hat, or at least that’s what the guys at the Old School Hat-Wearing Institute told me when I facebook-spammed them for comment on the matter.

But whatever you do, DO NOT end the spin of the hat with your hat to the back. You are not Kriss Kross and you’re not Crash Davis or Spike Nolan, so rock that hat frontwards, son!

Spike Nolan
Only reason to wear your cap backwards is if you’re signaling Monty Brewster to throw you the slider in the top of the 6th.

8. Then you smooth the hat

Even after all the steps above, you want your hat looking nice and smooth. Take each of your palms and from the sides of your head, glide your hands toward the front of the brim, all the while smoothly pressing the hat so that it aligns with your head. Too often, people put on their hats and just let them sit there and it looks like a botched boob job– you can tell one side’s a bit higher or lower than the other. You don’t need a leveler from Home Depot, just do the eye test and smooth that bad boy out!

9. But hey! Don’t forget, look for the star!

Again, this is a Starter ad. Nowadays, I guess you look for the NewEra logo or wherever you got the hat from. I’m a comic book fan, so most of my hats when I wear them will have some kind of Marvel or DC logo on ’em, but hey Doowutchyalike!

It’s Clobberin’ Time!


Well, that’s all the steps in how to wear a ball cap the old school way!

Special thanks to DJ Jazzy Jeff for aiding me in this instruction post. You can follow the legendary hip hop icon on twitter @djjazzyjeff215 and tell him thanks for setting you straight (but never straight brimmed!).

Your finished product should look like this:

Image via

Oh yeah, if you’re in need of a remedial course, follow-up with Jazz as he schools the late, great Rodney Dangerfield!


Well, that’s my submission for this week’s edition of The League of Extraordinary Bloggers. Like what you’ve read? Did I miss any? The comments are further down the page, add yours!

Also, check out these other awesome entries from fellow (and lady) League bloggers. Most chose to blow up the Death Star, but there are some funny (and some disturbing) how-to’s in this mix:

Primordial Badger’s Media Hoard

Green Plastic Squirt Gun

Monster Cafe Saltillo

Of Flying Monkeys and Ewoks, Oh My!

Random Nerdness

Crooked Ninja Turtle Gang

Dork Horde



Q the Adult




7 Comments Add yours

  1. shezcrafti says:

    Thank you for this incredibly important contribution to fashion. The “trucker hat” trend drives me crazy and MUST be stopped. These kids would have gotten their asses beat down where I come from.

    I was also a fan of Ya Kid K’s backward, off-to-one-side hat style –> ( I can only dream of being as funky fresh as she was back in the day.

    1. Ashton Kutcher during the “Punk’d” years and Judah Friedlander are the only guys other than real truckers who can pull off the trucker hat style.

      Ya Kid K was so underrated as a rapper. Nevermind I spent the early part of the 90’s questioning her gender as if she was Pat from SNL…

      1. shezcrafti says:

        You’re not alone there, dude. I think we all did. Of course it didn’t help matters that Technotronic chose to put a hot chick in their videos instead of Ya Kid K to lip sync her parts. =/

  2. Only Classick could compare a crooked hat to a botched boob job. Awesome.

    1. Sorry I didn’t offer any photo links of botched boob jobs. Only so much I can do during lunch hour!

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