How to Wear a New York Yankees Fitted (2024)

How to Wear a New York Yankees Fitted (1)

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Illustrations by Naomi Otsu

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 haveis 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 tipstoanyteam’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 New York Yankees Fitted (2)

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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 andif 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 New York Yankees Fitted (3)

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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 bigand you need to shrink the fitted hat, justwet 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 sweatbandto 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 New York Yankees Fitted (4)

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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 New York Yankees Fitted (5)

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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.Iffor 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 New York Yankees Fitted (6)

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Let your inner creativity roam free as you look to make your Yankee fitted, yours. Add patches, embroidery, etc., butTECHNICALLY 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 withcity-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 New York Yankees Fitted (7)

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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 New York Yankees Fitted (8)

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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 fiveplayers 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 New York Yankees Fitted (9)

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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.

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How to Wear a New York Yankees Fitted (2024)


How should a fitted baseball hat fit? ›

The cap must be deep enough in order for it to fit around the head. While it should not be too tight, the cap should be the mold of your head size, with a little room to spare to avoid uncomfortable tightness. I always avoid loose-fitting hats because they fall off easily.

How should a fitted hat feel? ›

The hat should sit comfortably mid-forehead above your eyebrows and not obstruct your view. The sweatband inside the hat should provide a snug fit, not a tight fit. If you feel any tension or end up with deep red marks on your forehead, pick a looser-fitting hat.

How can I make my fitted hat fit better? ›

Hat size reducer tape can often make a cap at least one size smaller. You'll find varieties in foam or cloth materials with an adhesive backing that makes the tape stick to the inside of your hat. The extra material fills the hat and gives it a snug fit, effectively letting you shrink the crown of a hat.

Is it better to size up or down in fitted hats? ›

If you are between sizes, buy the larger size. Hats will often shrink, especially if they are made of wool so getting a hat that is just a little too tight will become increasingly uncomfortable over time. Size matters, but so does style when it comes to getting the perfect fit.

Should a baseball cap touch your ears? ›

Avoid forcing your baseball cap on your head because doing so could cause your ears to protrude. You ought to be able to wear the cap comfortably without exerting excessive pressure. You might need to purchase a new baseball cap if the one you have always pushed your ears out when you wear it.

Do fitteds stretch over time? ›

Of course, the first step in stretching out a fitted baseball hat is to wear it. Many times, a baseball hat will stretch out as it gets broken in, but that is not always the case. If your baseball hat doesn't loosen up over time, the next step is to try hot water.

Do fitted hats stretch as you wear them? ›

Wearing a hat will naturally stretch it out and you'll get comfortable with the fit. This will give you time to notice if it feels too tight, too loose or if there is no need to make adjustments at all.

What is the average fitted hat size? ›

The most common male size is 7-⅜ and the average hat size for females is 7-¼.

How many inches is a size 7 fitted? ›

Hat Sizing Chart *
Head CircumferenceAdult Hat Size
21 5/8556 7/8
22 3/856.87-1/8
9 more rows

Why do people wear Yankees hats? ›

In the US the Yankees were a very successful team and that team has always had a large fan base. Internationally the NY Yankee logo is seen a being a symbol of NYC and one sees it being worn on caps and clothing by foreign entertainers.

What color cap goes with everything? ›

Your best pick: On a practical note, dark color caps will go with most anything, and best hide signs of frequent wear (sweat on the inner band, anyone?).

Why are Yankee hats so popular? ›

Why do so many people wear Yankees hats? They are the most popular, celebrated, winningest, and one of the older teams in MLB history that's why the hat is so ubiquitous. Also, they pay in, for, and represent one of the largest and most glamourous cites in the world.

How do you look hot in a baseball cap? ›

How to Make a Baseball Cap Look Feminine #1: Do your hair and wear it down.
  1. Blow out that hair and curl it if you're feeling extra sassy. ...
  2. Adding jewelry will always make an outfit look better. ...
  3. If you're not liking how you look with the traditional way of wearing your baseball cap, try flipping it backward!
Mar 9, 2023

What face shape looks good with baseball caps? ›

A baseball cap, newsboy, or fedora flatters a heart-shaped face. A nicely cut brim or angle can soften the wideness of your top face and the narrowness of your jaw.

Does wearing a hat make you look attractive? ›

Caps help you draw attention and make you stand out from the crowd. Wearing a cap will complete your look - it's a simple yet great accessory to make you look confident. Whether you prefer to wear it as a sporty accessory or a fashion statement, the cap will make you hold your head up high.

Why does my fitted hat feel smaller? ›

Wool and cotton shrink with heat and moisture, and your head will amply produce these elements while you wear your hat. So give your new ball cap a little wiggle room to shrink down to fit the contours of your splendid dome.

Does weight affect hat size? ›

The other thing that people don't realize is if you lose weight or if you gain weight, your head size changes. So if you've lost a lot of weight, your hat may feel very big on your head, but not to worry. You bring it in and we'll make it smaller for you. If you gain weight, we'll make the hat larger.

Why do my fitted hats fit differently? ›

All New Era hats are handmade in different factories. This means that you may occasionally get a slight variation in sizing even between the same size hat in the same style. It's just the production variation that sometimes occurs.

How do you stop my ears sticking out when wearing a cap? ›

If your ears stick out, like mine do, Fugate suggests wearing the hat a little further back on the head and tipping it up a little, so you can see the underside of the brim. "This elongates and draws the eyes upward away from the ears," he says.

Where should a baseball cap sit on your head? ›

The easiest way to measure your head for a hat is to hold a piece of string and measure around your head where the cap will sit. Usually, this means you'd hold the string about 1/8 inch above the forehead and ears. Make sure not to pull the string too tight or hold it too loosely, or you won't get a perfect fit.

Does curving a fitted hat make it bigger? ›

No it doesn't make it anywhere near a full size different. If it's loose you might need a size smaller anyway but bending the brim only makes a slight diff.

Can everyone pull off a hat? ›

Anyone can wear a hat. You only need to become familiar with your face shape and what hat shape suits you. Use the information below to determine your face shape, and then read about what sort of hats suit you best and how to wear them.

Do fitted hats damage hair? ›

Well, dear wearers of ball caps and bowlers, rest assured: Wearing hats does not cause hair loss. Actually, let us caveat that. If you consistently wear an extremely tight hat, you could experience traction alopecia (gradual hair loss resulting from repetitive pulling or tension of hair).

Do fitted hats shrink with sweat? ›

Through regular exposure to sweat and sun over time, they'll shrink down to your size, but if you can't wait that long for a comfortable fit or bought a hat that's a whole size larger than your head, a little extra heat can go a long way.

Are tight hats bad for hair? ›

Consistently wearing your hat too tight can trigger another form of hair loss known as traction alopecia, which happens gradually as a result of continual tension or pulling and by inhibiting circulation.

How tight should a hat be on your head? ›

A hat should fit snugly around your head, but not so tight that it leaves marks across your forehead or cuts off circulation. Similarly, you don't want your hat to be too loose to ensure it doesn't fall off.

What's the biggest fitted hat size? ›

A L/XL (Large through Extra Large) hat would fit measurements just over 22 1/2 up to 24 inches, or hat size 7 1/4 to 7 5/8. If a hat does not list sizes, it is a 'one-size-fits-most' hat. It will fit sizes from hat size 6 3/4 up to 7 5/8.

Is a size 7 hat big? ›

Small hats (listed as size 6 3/4 – 6 7/8) are for heads that measure 21 1/8″ – 21 1/2″ (54 – 55 cm). Medium hats (listed as size 7 – 7 1/8) are for heads that measure 21 7/8″ – 22 1/4″ (56 – 57 cm). Large hats (listed as size 7 1/4 – 7 3/8) are for heads that measure 22 5/8″ – 23″ (58 – 59 cm).

What size hat is a 23 inch head? ›

In some cases, you may find men's hats listed as OSFM, or one size fits most. These OSFM hats will generally fit heads with a circumference of 21.5 inches to 23 inches or a medium/large.

How do I know what head shape my hat is? ›

Get a cloth measuring tape (you can buy them at any local convenience store), and measure your head where you like to wear your hat. We recommend measuring around the widest part of your head, which should hit the middle of your forehead and be 1/4 - 1/2 inch above your ears.

How can I measure my head without a tape measure? ›

If you don't have a measuring tape, a piece of string, knitting yarn, or even dental floss can work in a pinch. First, wrap the string around your head, starting and ending at one point. Then measure the length of string using a tape measure or ruler.

How many inches is my waist if I wear a size 7? ›

Back-waist length13.7514.25
1 more row

Is size 7 equivalent to 37? ›

Women's Shoe Size Conversions
US SizesEuro SizesInches
13 more rows

Can you wear fitted hats backwards? ›

Yes, they are. Backwards ball caps have been around for a while, and they aren't going anywhere fast. But it's not just the rich history of this trend that keeps it cool.

Should a beanie cover your ears? ›

The Standard. This method is the most effective for keeping you warm. Simply wear the beanie without cuffing it, so that it covers your ears. The front should rest just above your eyebrows.

How do you keep a baseball hat on with long hair? ›

The most common choice for long locks is to tie your hair up into a loose ponytail, secure it with an elastic band, and tuck it through the hat's back closure. This style is best with baseball caps that have an adjustable closure on the back. But you can also position the ponytail just underneath the hat.

Do you tilt hat to right or left? ›

Tilted or straight? A hat that 'tilts', always tilts to the right. This stems from the days you would be escorted by a man on your left. A fascinator or small co*cktail hat may also be worn tilting left.

Why do you store hats upside down? ›

When storing your hat on a shelf, it's important to flip the hat upside down and store it on its crown, not its brim. Storing your hat on its brim for a long period will put pressure on the brim causing it to change from its original shape.

Does your hat have to match your dress? ›

Complement your Dress

For your hat to look good with your dress, it should complement and match well. Before anything, ensure you're not trying to cover up a lousy outfit with your hat. It will only make the hat look bad and yourself even worse. Next, consider a hat that matches your dress tone.

What is proper hat etiquette? ›

Take hats off, including baseball caps

In someone's home. At mealtimes, at the table. While being introduced, indoors or out (unless it's frigid!) In a house of worship, unless a hat or head covering is required. Indoors at work, especially in an office (unless required for the job)

Do hats look better forward or backward? ›

Forwards-facing caps are more unassuming, while the backwards look is brasher and bares it all, emphasizing facial features, for better or worse—it can be a great look with a good haircut and tight hairline.


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