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Optimo south side mobsters

Judgmentalist

A-List Customer
Messages
492
Hey Guys - check this one out.

https://ebay.io/m/ibE87X

This guy wants 3k for this hat because it has an Optimo name tag.

I measured the weave based on the size of the word Montecristi on the sweatband of the one I have in hand. Assuming they haven't changed the font size, the absolute maximum WPI on this hat is 263. 225 is probably closer to accurate.

The full description says that he got it second hand. So my question is; is this guy nuts or is Optimo nuts?

Surely this was an entry level Montecristi for them, and would not have been sold for anywhere near what he is asking. I mean, the color is solid and the weave is nice and even, but even at 263 WPI that is below the lowest tier Montecristi Brent Black offers, which you can get for $650. I use him as a reference because I put them in the same category when it comes to name recognition, at least where Montecristi hats are concerned.

What do you think?

3k Optimo Montecristi.jpg
Photo Jun 29 2026, 11 39 47 AM.jpg
Photo Jun 29 2026, 11 40 03 AM.jpg
 

jeffgarf

One Too Many
Messages
1,264
Location
Jerusalem, Israel
Hey Guys - check this one out.

https://ebay.io/m/ibE87X

This guy wants 3k for this hat because it has an Optimo name tag.

I measured the weave based on the size of the word Montecristi on the sweatband of the one I have in hand. Assuming they haven't changed the font size, the absolute maximum WPI on this hat is 263. 225 is probably closer to accurate.

The full description says that he got it second hand. So my question is; is this guy nuts or is Optimo nuts?

Surely this was an entry level Montecristi for them, and would not have been sold for anywhere near what he is asking. I mean, the color is solid and the weave is nice and even, but even at 263 WPI that is below the lowest tier Montecristi Brent Black offers, which you can get for $650. I use him as a reference because I put them in the same category when it comes to name recognition, at least where Montecristi hats are concerned.

What do you think?

View attachment 795385 View attachment 795386 View attachment 795387
I think you are correct. I, myself, love looking at sellers who think they can get this kind of money. I don't waste my time every following them to see if they do, but it might be an interesting project to see where listings like this end up.
 

Judgmentalist

A-List Customer
Messages
492
I think you are correct. I, myself, love looking at sellers who think they can get this kind of money. I don't waste my time every following them to see if they do, but it might be an interesting project to see where listings like this end up.
I keep an eye on them, but the problem is when the listing goes down you don’t know what the resolution was. The hat may eventually be marked sold, but was it really? At what price?
 
Messages
19,435
Hey Guys - check this one out.

https://ebay.io/m/ibE87X

This guy wants 3k for this hat because it has an Optimo name tag.

I measured the weave based on the size of the word Montecristi on the sweatband of the one I have in hand. Assuming they haven't changed the font size, the absolute maximum WPI on this hat is 263. 225 is probably closer to accurate.

The full description says that he got it second hand. So my question is; is this guy nuts or is Optimo nuts?

Surely this was an entry level Montecristi for them, and would not have been sold for anywhere near what he is asking. I mean, the color is solid and the weave is nice and even, but even at 263 WPI that is below the lowest tier Montecristi Brent Black offers, which you can get for $650. I use him as a reference because I put them in the same category when it comes to name recognition, at least where Montecristi hats are concerned.

What do you think?

View attachment 795385 View attachment 795386 View attachment 795387
Caveat emptor.
 

Judgmentalist

A-List Customer
Messages
492
Caveat emptor.
Indeed. I had a good conversation with this guy. I ended up sending him pics of my Optimo Montecristi. Mine is a stingy-brim pork pie, so less marketable shape, but the weave is just as even and the color is just as good, and my WPI is 160% of his WPI. And oddly enough, both hats are the same size.

I’ll keep an eye on this one. Maybe if it ever sells I can get some more data.

I don’t think he’s actively trying to s crew anybody, just looking at big dollar signs on the Optimo website and assuming he got the deal of a lifetime when he bought it second hand. On the other hand, he said he has a bunch of Optimo hats, so he should hopefully have enough common sense to learn what he has.

Either that or that is how he is presenting intentionally.
 
Messages
19,435
Indeed. I had a good conversation with this guy. I ended up sending him pics of my Optimo Montecristi. Mine is a stingy-brim pork pie, so less marketable shape, but the weave is just as even and the color is just as good, and my WPI is 160% of his WPI. And oddly enough, both hats are the same size.

I’ll keep an eye on this one. Maybe if it ever sells I can get some more data.

I don’t think he’s actively trying to s crew anybody, just looking at big dollar signs on the Optimo website and assuming he got the deal of a lifetime when he bought it second hand. On the other hand, he said he has a bunch of Optimo hats, so he should hopefully have enough common sense to learn what he has.

Either that or that is how he is presenting intentionally.
If you’re not a buyer for his item why are you so interested? Sounds like the hat police.
 

Judgmentalist

A-List Customer
Messages
492
If you’re not a buyer for his item why are you so interested? Sounds like the hat police.
lol - “better data” sounds like the hat police?

You are reading me incorrectly, my friend. :) I’m a nerd. A researcher. Also a little obsessive. I find this interesting.

Half the fun of this hat stuff for me is learning about them. Not being able to get closing price data on sold hats drives me nuts.

And I am a buyer. I like Optimo. I like Montecristis. The hat fits me. If the price ever comes down to my price point I’d probably buy it.
 
Messages
19,435
And I am a buyer. I like Optimo. I like Montecristis. The hat fits me. If the price ever comes down to my price point I’d probably buy it.
That’s fine but why is that any business of anyone’s here whether you pay $3K or $5K? What you would have no way of knowing is there has been a history here of ebay Sellers being contacted by someone claiming to be an “expert from Fedora Lounge”. Don’t be another one of those.
 

Judgmentalist

A-List Customer
Messages
492
That’s fine but why is that any business of anyone’s here whether you pay $3K or $5K? What you would have no way of knowing is there has been a history here of ebay Sellers being contacted by someone claiming to be an “expert from Fedora Lounge”. Don’t be another one of those.
Okay, starting from the beginning:

1.) I take no offense at the direction this thread has taken. I hope no one else does either.

2.) You are correct; I was not aware there had ever been an issue with people pretending to be experts from TFL. That is interesting and useful information. Thank you.

3.) I would never claim to be an expert. In fact, the first thing out of my mouth is usually, "I'm not an expert," when people ask my opinion—which, for some reason, happens from time to time—so no worries there.

4.) I'm not sure I understand your question about whose business it is what I pay. The reason opening and closing market data is valuable to me is that I am actively and continuously updating my database on what any given hat is worth, both on the secondary market and to me personally. The more pricing data I can gather, the better my valuation skills become over time.
 
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Messages
19,435
2.) You are correct; I was not aware there had ever been an issue with people pretending to be experts from TFL. That is interesting and useful information. Thank you.
A prime example. A nephew listed a hat for sale he had inherited from his uncle. His mom seemed to recall that her brother bought the hat new around 1950 so the Seller dated the hat from that info. The hat had an OPS tag inside. The “expert” contacted the seller to tell him the hat could not be a 1950 because during the Korean War OPS tags were not used until Jan 1951. What was the point of that? Ego. Anyone serious collector interested in buying a hat at that level would know that & it wouldn’t bother him.
4.) I'm not sure I understand your question about whose business it is what I pay. The reason opening and closing market data is valuable to me is that I am actively and continuously updating my database on what any given hat is worth, both on the secondary market and to me personally. The more pricing data I can gather, the better my valuation skills become over time.
What difference should it make to anyone else except between buyer & seller if the seller lists the hat as an Ultra fino fino & it’s a basket weave? Priced at $500 or $3,000 or $5,000. The final transaction is a private transaction between buyer & seller. Caveat emptor.
 
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Judgmentalist

A-List Customer
Messages
492
A prime example. A nephew listed a hat for sale he had inherited from his uncle. His mom seemed to recall that her brother bought the hat new around 1950 so the Seller dated the hat from that info. The hat had an OPS tag inside. The “expert” contacted the seller to tell him the hat could not be a 1950 because during the Korean War OPS tags were not used until Jan 1951. What was the point of that? Ego.

A prime example. A nephew listed a hat for sale he had inherited from his uncle. His mom seemed to recall that her brother bought the hat new around 1950 so the Seller dated the hat from that info. The hat had an OPS tag inside. The “expert” contacted the seller to tell him the hat could not be a 1950 because during the Korean War OPS tags were not used until Jan 1951. What was the point of that? Ego. Anyone serious collector interested in buying a hat at that level would know that & it wouldn’t bother him.
I see what you are saying. I always hope you guys that know what you are looking at will jump in with that information. :) I’m still very shallow on dating vintage hats.
 

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