How To Pull Off A Fedora/Trilby Dress Hat

Hello fellow hat lovers. This is my first post. I am not sure if this topic was ever posted...it probably was, so please forgive me if you've heard all of this before. I am 47 and have wanted to wear a fedora since I have been 20. I never really did. I always felt silly - I know, it's my own problem...haha. A lot of you gents look GREAT by the way. Kudos. I have a black Dobbs Fifth Avenue. A Grey with black ribbon Fur Felt Stetson (when I was Frank Sinatra for a Halloween party), a fawn brown Biltmore. A charcoal grey Christy's fedora...a navy blue Christy's trilby...a few straw hats. I don't really wear any of these though. I want to though. I don't collect things to just collect them. The price of some fedoras are...crazy. Lock & Co. are gorgeous...but, $400 plus...I dunno. All I know what to look for is where these are made. I use the same logic with my baseball caps, suits, shoes: made in USA, England, Italy, Canada...you're probably getting a good quality product. Just recently I learned the difference between a Trilby and Fedora. They're all Fedoras, right? Trilby's just have shorter brims??

I really don't know how to wear one. I am not certain how to pull one off either. This is my problem. I use this as an illustration.... I have a pair of spectacular Allen Edmonds' spectators in walnut and white. I think a lot of men who like spectator shoes have a refined taste, and an adoration of things vintage. I don't see many men pulling these off well though. I think the way to pull off a spectator is to tone down EVERYTHING you're wearing. Solid color grey trousers. Solid shirt. Plain-ish tie. And there you go - you rock the hell out of these shoes. When you're wearing them with a chalk stripe suit...you look like you're in a costume. Just my two cents.

Not only do I still not know how to wear a Fedora/Trilby...I am not sure how it should sit. brim up or down? I think the brims up and the hat slightly tilted looks great, especially with my mug. I tried one on when I went to my parents, and they laughed at when I flipped the brim up...my dad said, "Well, Larry from the Three Stooges pulled that look off". I think he was serious. (smile). When I see old films, almost always in black and white, these guys look INCREDIBLE. James Stewart, Cary Grant, etc. When I google "Fedora" as an imagine search, I think most of these modern guys look...ridiculous - most of the time anyway. I once bought a Stetson Stratoliner that I ultimately sent back when my secretary said, "Oh, you look like a Mountie in that". She's Canadian and was trying to be nice, but that's not the look I was going for. Johnny Depp in a Stratoliner, or maybe it's a Borsolino, looks great....then again, he's wearing it with a t shirt at some Hollywood event. Maybe this is the trick. dress hats with casual clothes? But I wear a suit and wool top coat every day in the Fall and Winter.

Maybe this is just a rant, and I don't need any responses. I am not trying to be politically incorrect, but I can't be the only one on here that LOVES a well made fur felt fedora/trilby, but afraid to wear one in public...

Welcome PT,I suspect everyone here has felt the same concerns at one time.The general consensus is that you need to wear the hat vs letting the hat wear you.Just try it and enjoy it.

Hi, and welcome. I have only been an everyday hat wearer for a very short time. I never thought I looked good in a hat, and was fairly self-conscious about it. But one day I purchased a Panama on vacation and decided I looked pretty darn good in it. So down the rabbit hole I went, and the members here gleefully pushed me along, as they are evil enablers.

My advice? Put it on your head and own it. I haven't had any of the snarky feedback you've gotten, but the heck with them, right? Wear one every day, play with them - brim up, brim down, whatever. You appear to be a better, more complete dresser than I, so maybe your fashion eye is more critical, and you want to match your outfits. I just make sure my hat generally matches what I have on (earth tones with earth tones, etc), and I wear one with suits, jeans, shorts, and sometimes just sitting around the house in sweats and a t-shirt because I feel like having a hat on.

Somewhere on this forum, I think in the How Do Folks React To Your Hat Wearing thread, one of the long-time members posted a picture of a young Japanese fellow, pre WWII. He's obviously not dressed to the nines, and is doing some kind of outdoor work. The man's wearing a fedora and he owns it. Also, go look in the Non Shorpy Web All Stars thread. Look at how men wore hats when hat wearing was common. Businessmen, field laborers, clerks, salesmen, maintenance guys - all wore hats and they wore them in all kinds of situations. They look like they belong in them because, well, they do!

Now go put on a hat. And post some pics in the What Hat Are You Wearing Today thread. And we'll tell you you look great. And we'll convince you to buy more.

And then you're doomed.

the saying goes something like....'you wear the hat, the hat doesn't wear you'.. I guess you just need to start getting used to wearing a hat, and to start feeling good about yourself doing so. The fact is, the more you wear one, the more people expect to see you wearing it... So put that hat on, and enjoy it....

Hello, Paul T.,

Yes, there is a certain . . . reluctance . . . to be got over. I bought my first decent hat one December day in the '90s, as it was bitter cold and raining, and I said, "I need a hat." And for a wool felt, it was fine. But then The Sting ran on TV, and there were Redford and Newman with their fedoras, and I went back and sprang for a real Stetson fur felt. I haven't looked back. Well, okay, occasionally I've looked back. But it's always been nostalgia. (Fur felt top-of-the-line Stetsons for $75 back then . . . wow.)

I've found hats I like with dressy clothes (generally fedoras in the Bogart mold) and with casual, sem-Western clothes (the Open Road and variants on it) -- and sometimes you can switch. You just need to experiment a little, and pay as little attention as you can to other people's opinions.

The hats you have sound like a good start. Your best bet to investigate further would be to visit a real hat shop and try various models with various brim widths and crown heights on your head, and see what you look like in angled mirrors like at your tailor. An Open Road (the LBJ style, if you're not familiar with the model name) often looks a little odd when seen head on. But look at it in profile: That's a sharp hat for sure.

Oh, and I think brim down in front + curled up a bit in back looks best for most hats/most people. YMMV. But if you're trying for the Bogart/Stewart look, that's the way to start. (Compare how Bogey looked in most of his films, brim down, with the scene in Big Sleep when he deliberately turns his hat brim up and puts on some goofy glasses to go undercover. Night and day, right?)

Welcome, sir.

"When I see old films, almost always in black and white, these guys look INCREDIBLE. James Stewart, Cary Grant, etc. When I google "Fedora" as an imagine search, I think most of these modern guys look...ridiculous - most of the time anyway."

Pre-WW2 hats look different because they were different. They were generally considerably taller.
Crown heights on new hats after WW2 decreased, but most men didn't immediately replace their "old-style" hats with new ones, so the older look was still fairly prevalent for a few more years.

Roughly pre-1940, open crown heights of less than 5.5" were quite rare.
Nowadays, it is quite the opposite situation.

I've always admired Fedoras and wanted to wear one. Tried for over 40 yrs to do so. Felt I never looked right in them. 2 years ago I simply said I'm doing this and did. It Felt right. WHY...? Simply becuz I didn't care. Didnt care what people said. Didnt care what looked "proper." Didnt care what matched with what ensemble. Didnt care how I perceived my "look." All I cared abt was what hat I liked and enjoyed wearing. Dont over think it. Just wear it. All the rest will happen by itself.

JackieMatra said:

Welcome, sir.

"When I see old films, almost always in black and white, these guys look INCREDIBLE. James Stewart, Cary Grant, etc. When I google "Fedora" as an imagine search, I think most of these modern guys look...ridiculous - most of the time anyway."

Pre-WW2 hats look different because they were different. They were generally considerably taller.
Crown heights on new hats after WW2 decreased, but most men didn't immediately replace their "old-style" hats with new ones, so the older look was still fairly prevalent for a few more years.

Roughly pre-1940, open crown heights of less than 5.5" were quite rare.
Nowadays, it is quite the opposite situation.

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Yes. This was why I could never quite get the right look with the 1990s fedoras. Vintage and custom hats are, or can be, taller and straighter in the crown -- they have more of the 1930s-1940s-1950s "look." Several modern (2015) Stetson models have much more of the old vintage styling, but they cost nearly as much as a custom from one of the hatters here at the Lounge.

Benzadmiral said:

Yes. This was why I could never quite get the right look with the 1990s fedoras. Vintage and custom hats are, or can be, taller and straighter in the crown -- they have more of the 1930s-1940s-1950s "look." Several modern (2015) Stetson models have much more of the old vintage styling, but they cost nearly as much as a custom from one of the hatters here at the Lounge.

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There are, at present, only three non-custom-made hats available with "fedora width" brims of less than 3" and open-crown heights of at least 5.75" (and with practically no taper), that I know of.
They are the Akubra Campdraft, the Christys' of London Adventurer/Poet, and the Stetson Stetsonian.

As you get comfortable, gain confidence, and begin to receive compliments, you will see which hats work better for you by that feedback. I agree with BenzAdmiral in paying little attention to the opinions of others, but you'll feel the positive vibes clearly with certain lids more than others. ENJOY!!

When I'm dressed more formally I have the brim down and pulled low closer to my eyes. When I'm in casual wear/bar clothes, I cock it back on my head for a relaxed look. But throughout the day it's everywhere in between. Just wear it, man!

You guys are great! Thank you. The current hat that looks best on me I think is the Christy's Luciano. Found this on ebay for $70 ish. Love it. It's not as soft as I thought it would be, but it fits my head (57cm) and my face perfectly. I've been debating for a couple months now to buy the Christy's Knightsbridge fedora. The USD to British Pound is at the best rates in years, if not ever. What I thought I wanted was the Kent Trilby in Light Beige with brown ribbon. I LOOOOVE that color combination. But, I found another Christy's trilby on ebay - in navy, and I think that is what I got - the Kent. The brim is VERY small and I don't think looks great. It's s shame because the wool is super soft - almost velvety. Pardon my ignorance, but do they make fedoras for women? Last night when I tried this on I feared I got a ladies fedora..just by how small the brim is. The listing on ebay said the following:
$350 CHRISTYS Mens FUR BLUE HAT Derby Bowler TRILBY CASUAL FEDORA SIZE M 7 1/8. I doubt it retailed for this...but it is super nice. Can you fellas take a look...am I wearing a girly hat? (smile). Oh, I've taken a lint brush and steamer to it - it's pristine now.

Hiya!

Well, you do need to get over the first initial hurdle so to speak of getting used to having the hat on your head. ( at least how it worked for my hubs)
It's a habit like any other, you put on your coat, and then put on your hat.

Like said before, wear it with confidence. Your hats look nice, so I'm sure people will find them stylish. I have never met someone who thinks they don't look nice!
Sure, you get looks, but in a good way!
Once you get used to all that you won't be able to stop
I don't even go outside without something on my head...

Looks like the bow is on the proper side (left) to be a man's hat. If it was a lady's lid, (it's NOT) I still say Toughen up, and wear it. It's a keeper in my eyes!

You have too many excellent options already. Bring 'em out!!

I thought your opening statement was one of the most honest and accurate descriptions of the state of mind many of us were in when we first got into this: we liked the idea of hats and thought they were cool, but just couldn't see ourselves wearing them. The more you do wear one, though, the less and less you're self-conscious of it. As Esther says above, it gets to the point where you rarely go out of the house without one, and the more you wear a hat and find ones that suit you, the more people just get used to seeing you as someone who wears a hat.

Once you've worn a hat for a few weeks, it'll feel really odd not to have it on when you are out and about.
If you want to wear a hat, go for it and don't let anyone put you off.

Love these responses...thank you everyone!

Paul Trumbull said:

Love these responses...thank you everyone!

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You're wlcm. Now put on a hat!

One from the early millennium. My first stetson fedora from when I was Frank Sinatra for Halloween - haha. My eyes have gone bad in the years since... ;-)

Paul Trumbull said:

One from the early millennium. My first stetson fedora from when I was Frank Sinatra for Halloween - haha. My eyes have gone bad in the years since... ;-)

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There you go! Ya look great in a hat.