Need some feedback on wearing fedoras

[RedReddingtonFan]

Good day gents,

Some of you may be familiar with the show, The Blacklist. If not and you enjoy crime, I highly suggest it. Well, the main character (Raymond Reddington) wears fedoras and the first time I saw one I immediately fell in love.

I actually managed to find the man who made the hats for the show, Mr. John Penman (penmanhats.com) and would love to purchase one for myself one day, once I have a little more money set aside

My predicament however, is I'm not the best dressed man out there and, I'm not really a man yet either. Firstly, I'm only 20 and a lot of what I've seen/read makes me think fedoras are more of an older man thing. Is 20 too young to be able to enjoy these fantastic hats?

Secondly, I tend to dress pretty casually. Some clean jeans and a nice t-shirt or button down. Again, a lot of what I have seen/read indicates that fedoras are more of a "fancy" piece of head wear. Would wearing one in a more casual way be acceptable or do I need to try and find another type of hat to fit my style?

Thanks!

 

[Boomerang]

Welcome to the Lounge!

I had many of the same questions, some years back. A casual stroll around this site will show you folks of all ages, genders and fashion styles looking positively stunning in their various hats. In my opinion, whether a person looks "good" in their hat or not is largely dependent upon the level of comfort that person experiences while wearing the hat in question. If you're confident that you look good in your hat, you probably do. If you're self-conscious, you might draw some sidelong glances.

That said, much has been written on this site for those new to wearing hats. I found a lot of it very applicable.

I say good luck to you on your hat journey, and again: welcome!

 

[RedReddingtonFan]

Welcome to the Lounge!

I had many of the same questions, some years back. A casual stroll around this site will show you folks of all ages, genders and fashion styles looking positively stunning in their various hats. In my opinion, whether a person looks "good" in their hat or not is largely dependent upon the level of comfort that person experiences while wearing the hat in question. If you're confident that you look good in your hat, you probably do. If you're self-conscious, you might draw some sidelong glances.

That said, much has been written on this site for those new to wearing hats. I found a lot of it very applicable.

I say good luck to you on your hat journey, and again: welcome!

Thank you, I really appreciate the feedback and encouragement. I will look around the site and look forward to hopefully sharing my hat you everyone someday soon

 

[Olumin]

I could just say: "dont care what others think"; and while that would be ideal, it doesn't help you much, because you do care. So for now, just accept it and move on. The goal is not to look "good" to others, but to start looking "good" to yourself.
What I suggest is to start with a slightly more casual hat, and from that move onto a more traditional dress hat. That way you will build up the confidence to wear whatever you want.

You can get a fedora-type hat with a narrow ribbon, like a Stetson Stratoliner or Akubra Campdraft (or anything similar), which will go well with casual outfits. Maybe wear the button-up instead of the t-shirt, and people around you will eventually get used to it. At some point you will be comfortable enough to wear whatever hat with any outfit you want. That's the goal.

If you feel too young to "pull off" more traditional clothing, look up "The report of the week" on YT. I believe he uploaded some videos on how he first got used to wearing what he does. I know it inspired me when I first watched it.

You could of course just get the hat you like straight away, but if you're to embarrassed to put it on in public it wont get you anywhere.

 

[Monte]

Welcome. Everybody wears hats. Trucker caps, baseball, beanies, felt and straw westerns. Not many wear fedoras, but I have, and used to have a modest collection myself. It's a piece of clothing, not unlike a good suit, that takes a little getting used to. People often comment on them, mostly positive. I'm glad you're saving money. May you wear yours well, no matter how casually or dressy you choose. By the way, enjoy your youth from this older guy.

 

[ILB Frank]

I could just say: "dont care what others think"; and while that would be ideal, it doesn't help you much, because you do care. So for now, just accept it and move on. The goal is not to look "good" to others, but to start looking "good" to yourself.
What I suggest is to start with a slightly more casual hat, and from that move onto a more traditional dress hat. That way you will build up the confidence to wear whatever you want.

You can get a fedora-type hat with a narrow ribbon, like a Stetson Stratoliner or Akubra Campdraft (or anything similar), which will go well with casual outfits. Maybe wear the button-up instead of the t-shirt, and people around you will eventually get used to it. At some point you will be comfortable enough to wear whatever hat with any outfit you want. That's the goal.

If you feel too young to "pull off" more traditional clothing, look up "The report of the week" on YT. I believe he uploaded some videos on how he first got used to wearing what he does. I know it inspired me when I first watched it.

You could of course just get the hat you like straight away, but if you're to embarrassed to put it on in public it wont get you anywhere.

This advice isn't bad... It's pretty much how I started wearing hats (again - after many years). But I quickly found that the "starter hat wasn't going to cut it for me and quickly moved on to the hat(s) I really wanted to wear.
I would encourage you to wear the hat you want. Fedoras aren't really that formal. Besides, have you seen what people are wearing on a daily basis these days? It's anything goes (literally). You won't stick out as much as you think (or are worried) that you will.
I've been known to wear western hats with shorts and tennis shoes and still get a compliment about the hat. As a matter of fact, the only thing I don't wear with a western hat is the one thing you're supposed to wear... Cowboy boots. (I do have a pair, but I only wear them if I go to a rodeo.)
It might be easier said than done but get "Redington" style hat, get dressed so that it looks comfortable and decent to you, and convince yourself to go about your day as if you were wearing the same thing you've always had on. For better or worse, people just aren't going to notice.

 

[Olumin]

This advice isn't bad... It's pretty much how I started wearing hats (again - after many years). But I quickly found that the "starter hat wasn't going to cut it for me and quickly moved on to the hat(s) I really wanted to wear.
I would encourage you to wear the hat you want. Fedoras aren't really that formal. Besides, have you seen what people are wearing on a daily basis these days? It's anything goes (literally). You won't stick out as much as you think (or are worried) that you will.
I've been known to wear western hats with shorts and tennis shoes and still get a compliment about the hat. As a matter of fact, the only thing I don't wear with a western hat is the one thing you're supposed to wear... Cowboy boots. (I do have a pair, but I only wear them if I go to a rodeo.)
It might be easier said than done but get "Redington" style hat, get dressed so that it looks comfortable and decent to you, and convince yourself to go about your day as if you were wearing the same thing you've always had on. For better or worse, people just aren't going to notice.

I believe Ive written on this forum before:

"You're damned if you do and damned if you don't."
Other people will think what they want anyway, so you might aswell just do what you want to start with.

So my own position is quite clear. But considering the OP is self conscious enough to ask this question, I assume he isn't yet comfortable with wearing such a hat in public yet. So I looked at it from a more realistic angle.

Getting the "starter" second hand is always an option if the OP wants to get it on the cheap. But by all means, I support going for the one he really wants right away, if he thinks he will wear it.

 

[Monte]

It just struck me while removing my timepiece, not many people notice it, but I do, and enjoy winding it every evening. Kind of like wearing a nice lid like the all the cool fellows did back in the good old days. Never left the house without one, in fact.

 

[Rmccamey]

Formal...or not...be yourself. Welcome to the Lounge. After a time or two out, it will become "old hat" to wear a hat. You will be surprised at the complements you receive.

Good day gents,

Some of you may be familiar with the show, The Blacklist. If not and you enjoy crime, I highly suggest it. Well, the main character (Raymond Reddington) wears fedoras and the first time I saw one I immediately fell in love.

I actually managed to find the man who made the hats for the show, Mr. John Penman (penmanhats.com) and would love to purchase one for myself one day, once I have a little more money set aside

My predicament however, is I'm not the best dressed man out there and, I'm not really a man yet either. Firstly, I'm only 20 and a lot of what I've seen/read makes me think fedoras are more of an older man thing. Is 20 too young to be able to enjoy these fantastic hats?

Secondly, I tend to dress pretty casually. Some clean jeans and a nice t-shirt or button down. Again, a lot of what I have seen/read indicates that fedoras are more of a "fancy" piece of head wear. Would wearing one in a more casual way be acceptable or do I need to try and find another type of hat to fit my style?

Thanks!

 

[RBH]

Welcome!!!
As stated just start wearing a hat and it will become 2nd nature.
As to Reds fedoras, most if not all were Borsalino hats.
I am not sure any Penman hats made it on screen.

As seen in this shot you can see the Borsalino on the bow keeper.

Check out this thread.

Again welcome and I hope you enjoy wearing your hats!!!

 

[RedReddingtonFan]

Welcome!!!
As stated just start wearing a hat and it will become 2nd nature.
As to Reds fedoras, most if not all were Borsalino hats.
I am not sure any Penman hats made it on screen.

As seen in this shot you can see the Borsalino on the bow keeper.

Check out this thread.

Again welcome and I hope you enjoy wearing your hats!!!

If they really were Borsalino, then why did Penman make them, just to not be used?

 

[hatsRme]

If they really were Borsalino, then why did Penman make them, just to not be used?

The production company paid him, that’s why! Once purchased, they can do as they wish with the hat. It’s possible Mr. Spader simply preferred the Borsas.
Penman, the insufferable self-promoter, may have made them for free, just for bragging rights, but then not to the taste of Spader. Just my speculation…

 

[The Lost Cowboy]

Good day gents,

Some of you may be familiar with the show, The Blacklist. If not and you enjoy crime, I highly suggest it. Well, the main character (Raymond Reddington) wears fedoras and the first time I saw one I immediately fell in love.

I actually managed to find the man who made the hats for the show, Mr. John Penman (penmanhats.com) and would love to purchase one for myself one day, once I have a little more money set aside

My predicament however, is I'm not the best dressed man out there and, I'm not really a man yet either. Firstly, I'm only 20 and a lot of what I've seen/read makes me think fedoras are more of an older man thing. Is 20 too young to be able to enjoy these fantastic hats?

Secondly, I tend to dress pretty casually. Some clean jeans and a nice t-shirt or button down. Again, a lot of what I have seen/read indicates that fedoras are more of a "fancy" piece of head wear. Would wearing one in a more casual way be acceptable or do I need to try and find another type of hat to fit my style?

Thanks!

If you haven’t already discovered it, I can recommend you spend time browsing/following the thread “What Hat Are You Wearing Today.” Here is a link:

What Hat Are You Wearing Today ?

Greetings All: Well....today i was planning on pulling out one of my most special, Stetson did it friggin alright, wear only for something special hat, just to brighten up my day. I was brushing it and noticed a thingy place, then a kinda unrecognized area and immediately went into “Panic...

www.thefedoralounge.com

On that thread, you will see all kinds of people wearing all types of fashion with all different sorts of hats. You’ll see the super well-dressed all the way down to dingy white t-shirts and even shorts (scandalous!). Great place to get some ideas for how folks today wear hats but also to see what styles of hats might suit your fancy.

And of course, feel free to post some photos of yourself in a hat or two (or 20… or 40… or…)

Welcome to the Lounge.

 

[RedReddingtonFan]

The production company paid him, that’s why! Once purchased, they can do as they wish with the hat. It’s possible Mr. Spader simply preferred the Borsas.
Penman, the insufferable self-promoter, may have made them for free, just for bragging rights, but then not to the taste of Spader. Just my speculation…

It sounds as though you don't like John?

Do you know which specific model of Borsa Reddington wore?

 

[T Rick]

It sounds as though you don't like John?

Do you know which specific model of Borsa Reddington wore?

Raymond wore a large number of hats in the 10 seasons of the show (my favorite show of the last decade). The vast majority of his hats were in fact Borsalinos. Even some of the Straws.

As for Penman, I don't know of any used in the show, but that may have happened. Any manufacturer so used (especially a small custom hatter) would I'd think use that in their promotions. But if you watch the series closely, you'll see a preponderance of Borsalinos, even I think from season one.

I'm enough of a fan that I've bought the Oliver Peoples Clifton sunglasses he wore. And I have a Browning Hi Power with wood grips, and a similar holster.

I don't yet have the Rolex GMT Pepsi he wore (maybe someday), but I do have a modded Seiko GMT that has a similar appearance. And oddly, I don't own any Borsalinos, despite a large hat collection with a lot of vintage. Mostly a Stetson man. But I do want to get a Borso similar to what Red wore. I need to get on that!

 

[RedReddingtonFan]

Raymond wore a large number of hats in the 10 seasons of the show (my favorite show of the last decade). The vast majority of his hats were in fact Borsalinos. Even some of the Straws.

As for Penman, I don't know of any used in the show, but that may have happened. Any manufacturer so used (especially a small custom hatter) would I'd think use that in their promotions. But if you watch the series closely, you'll see a preponderance of Borsalinos, even I think from season one.

I'm enough of a fan that I've bought the Oliver Peoples Clifton sunglasses he wore. And I have a Browning Hi Power with wood grips, and a similar holster.

I don't yet have the Rolex GMT Pepsi he wore (maybe someday), but I do have a modded Seiko GMT that has a similar appearance. And oddly, I don't own any Borsalinos, despite a large hat collection with a lot of vintage. Mostly a Stetson man. But I do want to get a Borso similar to what Red wore. I need to get on that!

I agree, probably one of my top 3 shows ever. Great character writing for Reddington and Spader played it so incredibility well

I do quite like his sunglasses as well. Personally I think the style could fit me decently and, of course, they go with fedoras nicely. That being said, $500 for some sunglasses is crazy... Ray Ban makes a model that is quite similar for $200, but even then I think $200 for some sun glasses is a bit absurd. For even cheaper, around $70, Shady Rays has some that are decently similar as well and are of course a much more reasonable price

I don't ever plan to get a Rolex. I think it's absolutely insane that they can charge what they do for simple device to tell time, but maybe a replica like you mentioned.

As for the hat, that's my biggest priority. I'm not sure what to buy, now that I know the Penmans weren't even used, at least much, but with how many different Borsos there are, I don't know which one to go for that would be closest to his, "typical" style

 

[T Rick]

I agree, probably one of my top 3 shows ever. Great character writing for Reddington and Spader played it so incredibility well

I do quite like his sunglasses as well. Personally I think the style could fit me decently and, of course, they go with fedoras nicely. That being said, $500 for some sunglasses is crazy... Ray Ban makes a model that is quite similar for $200, but even then I think $200 for some sun glasses is a bit absurd. For even cheaper, around $70, Shady Rays has some that are decently similar as well and are of course a much more reasonable price

I don't ever plan to get a Rolex. I think it's absolutely insane that they can charge what they do for simple device to tell time, but maybe a replica like you mentioned.

As for the hat, that's my biggest priority. I'm not sure what to buy, now that I know the Penmans weren't even used, at least much, but with how many different Borsos there are, I don't know which one to go for that would be closest to his, "typical" style

I found the glasses online for just over $300 (huge discount). There is a company that sells what look to be a credible Raymond Reddington sunglasses for about $80.

Point of clarification, my watch isn't a "replica", I'd never buy or wear one. It says Seiko on the dial, it does however copy much of the look of the Rolex. Difference between a "Replica" and an "Homage".

Best of luck in your search. I'll be picking up my 1st Borsalino this fall, not wearing felt in Summer months. Currently have 2 Stetson Straws and one Akubra felt on order. I should probably buy a Borsalino Straw too, maybe next Summer.

 

[RedReddingtonFan]

I found the glasses online for just over $300 (huge discount). There is a company that sells what look to be a credible Raymond Reddington sunglasses for about $80.

Point of clarification, my watch isn't a "replica", I'd never buy or wear one. It says Seiko on the dial, it does however copy much of the look of the Rolex. Difference between a "Replica" and an "Homage".

Best of luck in your search. I'll be picking up my 1st Borsalino this fall, not wearing felt in Summer months. Currently have 2 Stetson Straws and one Akubra felt on order. I should probably buy a Borsalino Straw too, maybe next Summer.

Still, mine are likely to get lost/damaged so I could never bring myself to pay that much. The $50 I pay every couple months for the ones I use now hurts me enough as it is

Oh my bad, I've never heard of that brand so I just assumed it was a replica

Yeah, summer probably isn't the best time for a felt hat, I'll likely get mine in the winter/fall as well when the time comes

 

[T Rick]

Still, mine are likely to get lost/damaged so I could never bring myself to pay that much. The $50 I pay every couple months for the ones I use now hurts me enough as it is

Oh my bad, I've never heard of that brand so I just assumed it was a replica

Yeah, summer probably isn't the best time for a felt hat, I'll likely get mine in the winter/fall as well when the time comes

Well this is ironic timing. It appears one year ago today was the final 2 episodes of The Blacklist. Found this Facebook post in my memories, thought I'd share it here. (The hat is a real, but generic Panama, bought here on the forum many years ago from a Seller who imported them from Ecuador and ran an annual sale). The glasses are the Oliver Peoples Clifton's. The Browning is older, Belgian and pretty much the same as Reddingtons. The candy is something he mentioned from Philly earlier in the season ("The Man With The Hat"). The holster is very close to one he wore.

"The Blacklist, Season 1 Episode 1. Since tonight is the series finale (2 episodes back to back beginning at 8:00), thought it fitting to go back to where it all started 10 years ago. And I've put together a few of Raymond's favorite things just for a lark."

 

[RedReddingtonFan]

Well this is ironic timing. It appears one year ago today was the final 2 episodes of The Blacklist. Found this Facebook post in my memories, thought I'd share it here. (The hat is a real, but generic Panama, bought here on the forum many years ago from a Seller who imported them from Ecuador and ran an annual sale). The glasses are the Oliver Peoples Clifton's. The Browning is older, Belgian and pretty much the same as Reddingtons. The candy is something he mentioned from Philly earlier in the season ("The Man With The Hat"). The holster is very close to one he wore.

"The Blacklist, Season 1 Episode 1. Since tonight is the series finale (2 episodes back to back beginning at 8:00), thought it fitting to go back to where it all started 10 years ago. And I've put together a few of Raymond's favorite things just for a lark."
View attachment 626809

That is a beautiful pistol, love the dark wood.

You really got his whole attire haha

Are Peanut Chews an east coast thing? I've been wanting to try them since I saw it in the show, but I can't find them anywhere over here on the west coast