How to Wear a New York Yankees Fitted

The New York Yankees fitted hat has had great significance in style & culture. Here’s how to properly wear & style a fitted Yankees baseball cap.

How to Wear A NY Yankee Fitted
Complex Original

Illustrations by Naomi Otsu

How to Wear A NY Yankee Fitted

America's favorite team representing America's favorite past time. The New York Yankees have characterized a lot of things that people, American and overseas, have long associated with the U.S.'s superior athletes. Celebrity. Success. Greed. Capitalism. Scandal. However, the cultural impact the Yankees have is unmatched. And if that impact had one symbolic relic, it would be the Yankee fitted. 

The significance of the Yankee fitted has had a monumental involvement in many facets of fashion, style, and culture for almost half a century, even as that world itself has gone through uncountable evolution cycles. What has changed about the Yankee fitted significantly over that time span is how people interpret it. The way they wear it. The color or elemental details of it. How to make it their own. So, we wanted to make sure we brought some of those unspoken rules to life with this guide covering how to properly wear a New York Yankee fitted. 

And yes, before you say anything, you can freely apply these tips to any team’s fitted hat. Dodgers fans. Phillies fans. Even you, Red Sox fans. There may be something here to help when it comes times to purchase your next fitted.

Size Correctly

How to Wear a Yankee Fitted size

By all means, wear your Yankee fitted the way you want, but if you don't want it too big or to be squeezing your brain out of your ears, there are a few ways to ensure you get the right fit. New Era slightly tweaked the sizing of their 59FIFTY official MLB fitted a few years back and it definitely had people in their feelings. You can go the route of measuring tape if ordering online. Or if you have the ability to try it on, give the brim a slight curve and if you can fit more than the tips of your pinky finger in by your temple, it’s probably too big. If you wear it for a minute and it leaves deep red marks on your forehead, it’s too small. 

Too Big? Too Small? Can I Shrink a Fitted Hat? Don't Worry.

How to Wear a NY Yankee Fitted

If you didn’t follow rule #1 correctly, do not fret, young padawan. Should you be right on the outskirts of too small or too big, there is a fairly simple trick to ensure it resizes to your domepiece. If it’s too big and you need to shrink the fitted hat, just wet the interior sweatband, but without damaging the exterior fabric, and then blow dry it to shrink the size down a bit. If you’re a bit lazier, you can also just purchase a cap liner or tuck some foam tape behind the sweatband to achieve that extra snugness. Too small? Do use the former method, but instead of blow drying, put the hat on while sweatband is still damp to help it stretch a bit. Science, dog. If you want to take things one step further, you could always shell out about $20 for a hat stretcher. These home remedies work, but one of these bad boys simplifies the stretching process even more.  

Don't be Afraid to Switch up the Color

How to Wear a Yankee Fitted Cap Color

Before 1996, New Era fitteds were only ever made in the official Yankee navy wool color. That is, until Spike Lee called in a special favor during the ‘96 World Series and asked for a red version, changing the landscape and the cultural significance of the Yankee cap on a global scale forever. It was unprecedented, but it started a revolution of modern notoriety that has, quite frankly, spiraled out of control a bit. These days, there are a startling amount of custom fitted options on the market to match your personal style, whatever it may be. And it isn’t just limited to switching up the colors of the crown and brim. Some caps sport throwback logos from the team’s storied history. Others trade in classic green or grey undervisors for hues like pink or baby blue. And due to the Yankees icon status, they usually are the team getting shown the most love in the custom world. Some purists prefer to, at the very least, keep the “NY” logo white on their fitteds. We understand. It’s important to honor history. But still keep an eye on what shops like Hat Club, MyFitteds, and Topperzstore are up to. One of their colorful customs may catch your eye and become your new favorite.

Please Remove the Stickers

How to Wear a NY Yankee Fitted Stickers

Yes, completely understand that this, too, much like any other piece of advice in this article, is preferential. But c’mon. It’s time to let that gold size sticker go. No one cares if you’re a 7 ¼. And no one cares if you bought the cap from Lids. Plus, you already know it's going to peel off and guess what? Now you’re dealing with a big ass discolored circle in the middle of your brim, bro. Just stop. If for some reason you prefer the gold size sticker remains intact, we just beg you to remove the barcode sticker fro the undervisor. There’s nothing aesthetically pleasing about that price tag peaking out from under your brim. 

Personalize It Yourself

How to Wear a NY Yankee Fitted Customize

Let your inner creativity roam free as you look to make your Yankee fitted, yours. Add patches, embroidery, etc., but TECHNICALLY you're ONLY allowed to add personalization to the sides and back, per New Era guidelines. So, whatever you do, do NOT seek out embroiderers in your area or online who may or may not do any kind of customization on the front of your cap for you on the low-low because that, my friend, is illegal. So, don’t do it. If you aren’t the most creative individual, don’t fret. There are plenty of fitteds on the shelves of your local shops nowadays that did the work for you by adding embroidered side patches to commemorate past World Series championships or All-Star Games. The patch you choose all comes down to personal preference. But if we are going to give a tip here, we suggest staying away from those fitteds flooded with city-specific embroidery like pizza slices or the Statue of Liberty. They are, to put it lightly, not the best.  

See if Your Favorite Brands Have Introduced Their Take on the Yankee Fitted

How to wear a ny yankee fitted

When you are a “man of the arts” we understand that it’s difficult to just rock a Yankee fitted that just anyone can grab. No, that’s beneath you. So hopefully you’re keeping tabs on all of the great NYC-based brands who have their own interpretation of the classic. Brands from Supreme to Aimé Leon Dore to Gucci have all paid homage, while institutes like the Museum of Modern Art have even commemorated their 2017 exhibit, “Items: Is Fashion Modern?” exhibit with their own “MoMA” inscribed version of the cap.

Be Ready to Explain Why You're Wearing a Yankee Fitted

How to Wear a NY Yankee Fitted

Whether you're a die-hard fan of the team or you just appreciate the cap's significance in pop culture, people will always try to strike a conversation around the cap you should be prepared to answer. So, should you be wearing your favorite Yankee fitted somewhere around unfamiliar people, here are a few questions that may be tossed your way. Are you from New York? How do you think they’ll do this year? Did you see the game last night? They really stepped up their bullpen this year, but will they be consistent? Name five players on the current roster? Would you have sex with Derek Jeter if...OK, you get the point.

The Age-Old Debate: to Bend the Brim or to Not Bend the Brim?

How to Wear a NY Yankee Fitted Hat Brim

OK, yeah, we’re not touching this one. However, we will provide you with this advice; while you should do whatever YOU feel is right —and we truly mean that—if you’re looking for advice, the answer is all in the shape of your head. The bill should naturally bend itself if the cap fits your head snug. Beyond that, you just have to go with your heart...and maybe put on a pair of your favorite sunglasses, bend your brim until its touching the top edges and voila but YOU DIDN'T HEAR THAT FROM US, KID.

Latest in Style