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Tip of the Cap: The New York-Penn League

Tip of the Cap: The New York-Penn League

Estimated Reading Time: 13 Minutes

Ladies and Gentlemen, welcome to Tip of the Cap! Tip of the Cap is a weekly series from Turf Writers Ned Donovan and Andrew Wilhelm discussing Baseball’s most important accessory, the Baseball Cap. Is it a cap? Is it a hat? Does it really matter? We’ll probably be using both interchangeably. Every week we will look at each league from the Single A Minors all the way to the Major Leagues and ranking their top 5 and bottom 5 hats. What makes us qualified to do this? That’s an extremely good question.

The New York-Penn League is a Class A Short Season League in the Northeast. Their teams include:

In terms of the personal fandom of the authors, Andrew is a Detroit Tigers fan (Connecticut Tigers are the minor league affiliate) and Ned is a Boston Red Sox fan (Lowell Spinners are the minor league affiliate). Alright, LET’S DO THIS!


First up, the hats that don’t make the cut. These are the hats that make us go, “……why?” These hats are not good, and if you designed them, you should apologize to the world at large. But first, a word from our biases:

Andrew Wilhelm on Bucket Hats

They are the worst. This one for the Hudson Valley Renegades is especially bad. But all bucket hats should never be worn unless you are fishing, and even then I am suspect on them. Therefore, I will not be including them in this list going forward. [Ned Note: I agree, though I like them on toddlers and babies. And my granddad used to kill it in one.]

Ned Donovan on Gendered Hats and Camo Hats

Look. A hat is a hat. If you make a pink hat, fantastic. If you only make them in smaller sizes because they’re “lady” hats? Get bent. Also I just generally hate Camo caps. Like if you have a Camo cap, it’s probably on the bottom tier of hats for your team. So I’m going to stay away from Camo hats, but the pink hats? They’ll definitely be on the list. Okay. LET’S GO. [Andrew Note: Camo CAN be done right, just see the latest Memorial Day MLB hats, but I agree that it’s few and far between it gets pulled off properly.]


Andrew Wilhelm – Connecticut Tigers – “Lobster Rolls” 59Fifty

On July 14, the Connecticut Tigers will take the field as the “New England Lobster Rolls” and wear specialty jerseys and this hat. The concept is fine with me, but the logo makes me extremely uncomfortable. I’m not entirely sure why, but I am not left with good feelings by that crustacean’s expression. Hard pass. [Ned Note: I am from New England. The concept is not fine to me.]

Ned Donovan – Auburn Doubledays – New Era Diamond Era Grey Doubledays Cap

Do I completely hate this hat? No, it’s redeemable. The Auburn (…Doubleday? I don’t know what a Doubleday is, so I’m going to assume that guy is one) is cool, but my problem is with the mechanics of this piece. The text? Awesome, love the slight serif, love the angle and slope, you know what I don’t love? This pitcher. This ball is about to bean my man Double Day in the face. He can’t hit that ball, and if he does, it’s going to be a moonshot to the sky as he ducks to avoid losing teeth. So I’m choosing this hat purely from an annoyance with a designer who obviously wanted to kill the mascot. Also, grey hats are dope, and there should be more of them.


Andrew Wilhelm – Staten Island Yankees – “Pizza Rat” 59Fifty

This is the same type of concept as the Lobster Rolls, but this time I hate everything about the concept of the “Pizza Rats.” Not because of the name or the fact that fans voted on it. No, simply because it’s the Yankees’ fans that came up with it. Also, the logo itself is cluttered and unimaginative. [Ned Note: Also, the bite out of the crust of the pizza is a weird choice. Like this rat is mad, but first he got hungry? Or did we interrupt his dinner?]

Ned Donovan – TIE
Vermont Lake Monsters – Black on Black Tonal Snapback Cap
Hudson Valley Renegades – ’47 Brand Red Out Snapback

Hokay so I didn’t mention this in my “here are my biases” statement, but I probably should have. Contrast is important when it comes to logos, and a single color hat to be artsy is dumb. On that left hat you literally can’t see the Lake Monster. THE LAKE MONSTER IS COOL. Why even wear it? If you’re gonna brand something with a team, wear that team proudly. This one on the right is less egregious due to the popout, but I can’t imagine walking down the street seeing that hat, and not wondering what the hell the logo is. I want to high five you for your hat, or boo you in mock condescension of hating your team, not stare perplexedly. Both of these hats are losers. Don’t wear them.[Andrew Note: The only exception in my mind is if you are allowed to wear a cap at work but it needs to be solid black. Think theatre technician. If you want to support your team this is the only way. But you should definitely only wear that hat at work]


Andrew Wilhelm – West Virginia Black Bears – Women’s Black WV Glitter Hat

Oof. This isn’t specifically so much about this hat as it is this logo. It looks like the “graffiti” you would seen in a bad 90’s after school special. Add to the fact this hat is specifically covered in glitter, and well, yikes. Sorry ladies, but you can find much better things to put on your head than this.

Ned Donovan – West Virginia Black Bears – Womens Pink Hat

Interesting that West Virginia gets both of our ires at the #3 slot. Here we are talking about my bias, which is Pink Caps. However this one I want to talk about more, because this is a pink cap that violates the rule from #4. What is this contrast? I can’t see this logo. Which is probably just as well, because I agree with Andrew’s assessment of this bad graffiti tag logo. Stop gendering hats, if I want to wear a pink hat I want to wear a pink hat. But I would never want to wear this pink hat, because it’s stupid.


Andrew Wilhelm – Lowell Spinners – 2018 Stars & Stripes 59Fifty

This is apparently a minor league version of the amazing hats featured on the 4th of July in the Majors. Except it’s lacking any stars or stripes. To make matters worse, this logo is next to impossible to clearly make out. Way too cluttered. [Ned Note: I kind of dig the New York Penn League logo on the side. If you click through to the purchase page, I think that’s a nice touch. Agreed on this train wreck of a design, though]

Ned Donovan – Brooklyn Cyclones – Coney Island Franks Cap

I have so many thoughts about this hat. Let’s start with this terribly contrasted logo. They did a great job outlining it in Black, and then had all the inside be the same gold/yellow badly outlined in white. Like…why? Next let’s talk about what’s happening. I’m not entirely sure. He’s a hot dog, he’s got a straw hat, he’s holding a baseball bat that might be a walking stick, the bun is on the right side (but I’m not sure about the left), and then he’s got a bowtie and is….peeing? What is the mustard trail? What does it represent? I don’t get it. This dude looks like Mr. Peanut’s totally unsuccessful little brother. [Andrew Note: This hat was No. 6 on my list.The mustache offends me deeply by just existing]


Andrew Wilhelm – Mahoning Valley Scrappers – Authentic Home 59Fifty

This is a hat the MV Scrappers wear as a regular occurrence at home games. IT. IS. AWFUL. It seems like they are trying to make it so the ventilation holes at the top of the hat act as the eyes of the dog, but that creates an extremely weird proportion issue. Also, this dog has a serious underbite. The more I look at this thing the worse it becomes, which is actually kind of impressive. This definitely belongs on the scrap heap. (Get it?)

Ned Donovan – Mahoning Valley Scrappers – Authentic Home 59Fifty

Do we need to see the hat again? I don’t want to put the hat again. Alright, I guess we need to see the hat again.

This. Hat. Is. Terrible. The ventilation grommets as eye holes are terrible, and I refuse to believe that it’s not on purpose. What should be a snarling, angry dog, is reduced to an awkward pup with a severe underbite. He’s cute as hell. There’s nothing menacing about this hat, but it’s obviously trying to be. Also that nose is without question a mushroom that they traced. I know dog noses look a little like a mushroom, but that is straight out of a cooking video game. Ditch this hat. It’s bad. It literally is the hat incarnation of Phteven.

Top 5

Here we go! Halfway mark. Now it’s time for the best of the best. The hats that we are putting in our purchase carts right now. Without further ado, here are our Top 5!


Andrew Wilhelm – West Virginia Black Bears – Alternate 59Fifty

Now this is more like it West Virginia. Please dump that other logo in favor of this much better bear logo for your main choice of head wear. The color blocking of this hat also receives top marks. It proudly displays the colors of its MLB Affiliate Pittsburgh Pirates, but also manages to be unique to the Black Bears.

Ned Donovan – Lowell Spinners – New Era Navy/Red BP 59Fifty

I’m a sucker for good coloring, and this hat is nailing it. The red being only the yarn, the brim, and the button on top? It’s a great accent. And a surprisingly little amount of white allows the logo to pop from the outline. I always feel like this logo is too busy but this hat is nailing it. Plus usually the New Era flag bothers me but it feels like a nice accent to this one. A+ design work. Also the yarn making an unobtrusive ‘s’? GREAT work designers. [Andrew Note: What the hell is a spinner? Some of the hats, like above, have a dragon that reminds me of Mushu. And then some, like this one, are just yarn around a bat. I DON”T UNDERSTAND] [NED DOUBLE NOTE: There were huge factories in Lowell for spinning yarn and using machines to weave that were entirely staffed by women. In middle school we took field trips to them. Hence, the Spinners.]


Andrew Wilhelm – Aberdeen IronBirds – Maryland Cap

At some point, all teams from Maryland try to incorporate the Maryland state flag into their uniform designs. Typically this fails in epic, “need to burn my retinas” type of ways. But this hat is very well done. I particularly like the split color on the excellent IronBird logo that perfectly accents the flag motif on the brim without over doing it. I also applaud the decision to leave the crown button black instead of a contrasting color. [Ned Note: Generally speaking my motto is “don’t yuck someone else’s yum”, but this is a bad hat, and you should feel bad, Wilhelm. This was the last hat I eliminated from my “worst” list]

Ned Donovan – Staten Island Yankees – New Era Alt 2 Fitted

It hurts me to write that I like something related to the Yankees. But I even texted Wilhelm during the writing of this “The Staten Island Yankees have some FLY hats!” And it’s true. This team knows how to have a hat repertoire. They even have a kids hat that I wish came in adult sizes to wear on certain occasions. That’s some shit. This hat, though? This hat is STRONG. The logo is rockin’, you can see it from a mile away, and it’s unique. I feel like it’s the logo the New York Football Club wished they had. I am a New Englander who now lives in NYC, and I refuse to buy a hat supporting anything called the Yankees. But if I were from Staten Island? I would rep this with pride. Shoutout to the single subtle gold star on top.


Andrew Wilhelm – Hudson Valley Renegades – 2018 Home 59Fifty

This hat is fantastic for a couple reasons. For one, it properly executes what I think the Scrappers failed so miserably at. But more importantly, the eyes GLOW IN THE DARK. And this isn’t some gimmicky specialty hat. This is their everyday home lid. It’s cartoony in a way only Minor League teams can get away with, but that’s part of the Minor League charm. And this is a near perfect execution of that. [Ned Note: I agree. The only reason I didn’t pick this one was because I wish the bottom of the animal was aligned with the bottom of the panel/top of the brim. But a great hat]

Ned Donovan – State College Spikes – Away 59Fifty

I. Love. This. Hat. I’ve almost bought it for years. I think the deer is dope, I think it’s completely unique, I love how simple it is, and I even love that the color scheme of the deer matches the MLB logo color scheme on the back. I know the MLB logo thing is standard, but for some reason it’s really effective on this one. This is one of those hats that sticks with you, and I want it. Plain and simple.


Andrew Wilhelm – State College Spikes – Away 59Fifty

Lots of MiLb teams have alternate logos that are a rather cartoony looking animal logo. The “deer head” logo for the Spikes is my favorite of the bunch. And the way it pops off this hat? Flawless. Honestly, this would probably be my number 1 if not for a bit of homerism on my part. I’ll explain in a second. But first, Ned, what’s your runner-up?

Ned Donovan – Vermont Lake Monsters – Official On-Field Alternate Cap

I slaved over this choice. SLAVED. Why? Because the Vermont Lake Monsters have the best hats of the bunch. They have so many rockin’ hats that I had trouble picking my top 3 off their team. Here’s #2. They even made me like a hat that violates so many of my design principles. However this hat is the winner because it’s both classic and eye-catching. That logo is weirdly ominous and friendly at the same time. The white water outline pops off the hat. The touch of blue for the fin and eyebrow doesn’t actually get lost, which I would expect it would. Also the New Era logo in green feels right. This is a fantastic hat, good on you Lake Monsters.


Andrew Wilhelm – Connecticut Tigers – Official On Field 59Fifty

The Detroit Tigers have the best logo and hat in MLB. The classic Old English D is just that: Classic. And I am a sucker for both classic looking designs and my Tigers. So when the Tiger’s affiliate took that logo and flipping it over with elongated tails to make a “C?” No other hat had a shot for this league.

Ned Donovan – Connecticut Tigers – Diamond Era Hat

While Andrew’s over there talking a bunch of nonsense about the Tigers having the best logo and hat in the MLB, he’s letting his bias get the better of him. Because indeed, this Tigers affiliate DOES have the best hat in the New York – Penn League, but it’s this one. This beautiful red/orange hat deserves all the attention. I agree with everything that Wilhelm is saying from a design choice above, but this color contrast catches my eye literally every time I see it. If it wasn’t so specific from a branding standpoint, I would own this hat. Without question, the flyest hat in the league.

In summation

Do you agree with us? Hate us? Do you have a hat that you think should be winning this battle? Drop it in the comments, tweet it at us, throw a picture of yourself wearing it on instagram and tag us @the_turf_sports. We’re on Facebook, Reddit, and even Linkedin if you care to follow us there. Right below where you’re reading this (well, past the ad), there are some share buttons. So it’s really easy to send this to your friends who will hate our selections. DOOOOO IT.

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