What to wear with a fedora....

[GHT]

My working life was spent in conservative suits. Hats, when worn, were black, dark brown and navy. Outside of work I shed the sombre look and embraced something much more flamboyant. But wearing a sports blazer like this one I would have, worn a cream coloured straw with, perhaps a hatband matching one of the stripes, probably the dark blue. It took a leap of faith and more than a dash of courage, but I have really come to like the bright coloured hats, (I have a couple of others.) Both blazer and hat have grown on me.

 

[Who?]

View attachment 588659
My working life was spent in conservative suits. Hats, when worn, were black, dark brown and navy. Outside of work I shed the sombre look and embraced something much more flamboyant. But wearing a sports blazer like this one I would have, worn a cream coloured straw with, perhaps a hatband matching one of the stripes, probably the dark blue. It took a leap of faith and more than a dash of courage, but I have really come to like the bright coloured hats, (I have a couple of others.) Both blazer and hat have grown on me.

Well, it certainly is a striking outfit, which not everyone could wear as well as you do.

 

[Juhani]

This was an interesting thread about how to combine headgear with shoes and clothes. After 26 pages, I can't resist sharing some acute reflections.

I always go with dark jeans, and with them, I put boots or dress shoes on. They go well with a stylish brim hat.

Nowadays, things are changing a bit as the economic situation is what it is. I must consider the versatility of shoes when buying them.

So, I tried to find out what are the most casual shoes ever worn with fedoras.

Google image searches show that until the 50s, men wore wide-legged straight trousers, but with them I have not seen anything other than dress shoes. The only exception I found, was the controversial member of the British royal family, Edward VIII, but here he's seen in a summer attire without a hat:
https://www.ivy-style.com/royal-style.html

I'm sure an attire of the kind could be completed with a Panama Hat. Indeed, digging deeper the Internet, I noticed that as early as the 1930s, a summer straw hat was seen in the fashion catalogues along with shorts and sneakers:

https://putthison.com/summer-1930s-summer-today-although-im-not/#jp-carousel-17076

Apart from these summerish styles, I see just dress trousers with dress shoes or working men's boots.

It's only when James Dean comes into the picture that I see jeans, and after that, it doesn't take too long to see jeans paired with sneakers. However, that's when hats went out of fashion, and men showed off their greasy hairdos.

Nowadays, jeans, sneakers and fedoras are seen in the style of Keith Richards:
https://www.alamy.com/rocker-keith-...st-end-of-london-uk-11310-image513624911.html

I can easily imagine men under 40 wearing skinny jeans, hoodies and colorful sneakers with a pork pie hat.

I'll be 50 next year, and I can't go out like that. However, I don't even go to the local food store without a wide brim fedora.

I decided that in addition to boots and few dress shoes, dark suede sneakers might work. The thing is, when I browse the catalogues of shoe shops, all the shoes under the category of "walking shoes" look suspicious.

When I combine a hat and shoes, I've found that if the shoes have clear-cut heels, they look better than shoes with flat bottoms. A flat sole goes easily with a lightweight straw hat, but a handmade beaver brim doesn't seem to fit well with lightweight shoes.

 

[Juhani]

Esquire, May 1934, shows a combination where modest sneakers are in harmony with a fedora hat.
https://www.thefedoralounge.com/thr...-mens-fashion-1933-1948-by-flanderian.102763/

 

[Who?]

This was an interesting thread about how to combine headgear with shoes and clothes. After 26 pages, I can't resist sharing some acute reflections.

I always go with dark jeans, and with them, I put boots or dress shoes on. They go well with a stylish brim hat.

Nowadays, things are changing a bit as the economic situation is what it is. I must consider the versatility of shoes when buying them.

So, I tried to find out what are the most casual shoes ever worn with fedoras.

Google image searches show that until the 50s, men wore wide-legged straight trousers, but with them I have not seen anything other than dress shoes. The only exception I found, was the controversial member of the British royal family, Edward VIII, but here he's seen in a summer attire without a hat:
https://www.ivy-style.com/royal-style.html

I'm sure an attire of the kind could be completed with a Panama Hat. Indeed, digging deeper the Internet, I noticed that as early as the 1930s, a summer straw hat was seen in the fashion catalogues along with shorts and sneakers:

https://putthison.com/summer-1930s-summer-today-although-im-not/#jp-carousel-17076

Apart from these summerish styles, I see just dress trousers with dress shoes or working men's boots.

It's only when James Dean comes into the picture that I see jeans, and after that, it doesn't take too long to see jeans paired with sneakers. However, that's when hats went out of fashion, and men showed off their greasy hairdos.

Nowadays, jeans, sneakers and fedoras are seen in the style of Keith Richards:
https://www.alamy.com/rocker-keith-...st-end-of-london-uk-11310-image513624911.html

I can easily imagine men under 40 wearing skinny jeans, hoodies and colorful sneakers with a pork pie hat.

I'll be 50 next year, and I can't go out like that. However, I don't even go to the local food store without a wide brim fedora.

I decided that in addition to boots and few dress shoes, dark suede sneakers might work. The thing is, when I browse the catalogues of shoe shops, all the shoes under the category of "walking shoes" look suspicious.

When I combine a hat and shoes, I've found that if the shoes have clear-cut heels, they look better than shoes with flat bottoms. A flat sole goes easily with a lightweight straw hat, but a handmade beaver brim doesn't seem to fit well with lightweight shoes.

I rather doubt that folks will be whispering behind their hands ….. “Oh dear, look at that chap over there, he’s wearing flat shoes and a fedora. Perhaps someone will take the poor fellow aside and help him.“

Wear your hat with whichever shoes you wish, and wear whichever shoes you choose with your hat. I really don’t think it’s that complicated.

Enjoy being probably the only guy in sight wearing a “proper” hat, and forget about the rest.

 

[Edward]

This was an interesting thread about how to combine headgear with shoes and clothes. After 26 pages, I can't resist sharing some acute reflections.

I always go with dark jeans, and with them, I put boots or dress shoes on. They go well with a stylish brim hat.

Nowadays, things are changing a bit as the economic situation is what it is. I must consider the versatility of shoes when buying them.

So, I tried to find out what are the most casual shoes ever worn with fedoras.

Google image searches show that until the 50s, men wore wide-legged straight trousers, but with them I have not seen anything other than dress shoes. The only exception I found, was the controversial member of the British royal family, Edward VIII, but here he's seen in a summer attire without a hat:
https://www.ivy-style.com/royal-style.html

I'm sure an attire of the kind could be completed with a Panama Hat. Indeed, digging deeper the Internet, I noticed that as early as the 1930s, a summer straw hat was seen in the fashion catalogues along with shorts and sneakers:

https://putthison.com/summer-1930s-summer-today-although-im-not/#jp-carousel-17076

Apart from these summerish styles, I see just dress trousers with dress shoes or working men's boots.

It's only when James Dean comes into the picture that I see jeans, and after that, it doesn't take too long to see jeans paired with sneakers. However, that's when hats went out of fashion, and men showed off their greasy hairdos.

Nowadays, jeans, sneakers and fedoras are seen in the style of Keith Richards:
https://www.alamy.com/rocker-keith-...st-end-of-london-uk-11310-image513624911.html

I can easily imagine men under 40 wearing skinny jeans, hoodies and colorful sneakers with a pork pie hat.

I'll be 50 next year, and I can't go out like that. However, I don't even go to the local food store without a wide brim fedora.

I decided that in addition to boots and few dress shoes, dark suede sneakers might work. The thing is, when I browse the catalogues of shoe shops, all the shoes under the category of "walking shoes" look suspicious.

When I combine a hat and shoes, I've found that if the shoes have clear-cut heels, they look better than shoes with flat bottoms. A flat sole goes easily with a lightweight straw hat, but a handmade beaver brim doesn't seem to fit well with lightweight shoes.

Yeah, jeans as a default for all occasions is a much more recent thing than we often realise, even moreso here in the UK. As I'm given to understand it from my parents' generation, even in the 60s turning up laces in a pair of jeans could be remarked on. I do remember my school lifting the ban on jeans for non-uniform days (uniforms are standard in UK & Ireland state schools, the equivalent of US 'public schools') somewhere around 1987. Until well into the 90s (and still in the village place my parents attend) turning up at a Sunday church service in a pair of jeans would be remarked on.

There were the 50s rebels like Dean, though as best as I can make out it's really the 60s generation than made jeans such a default. To the point where if I wanted to flash my rebel credentials in 2024, jeans would be the very last thing I'd put on.

In terms of shoes, I think it's important to remember that what we now think of as "dress" shoes - dress anything, really - wasn't such back when. Partly, people just had smaller wardrobes in general, but a pair of shoes was a pair of shoes - for the average person, you might have had boots for work. Common in my part of the world, and my dad still does this was folks having two pairs of shoes. One that got worn daily, the other for church on Sunday. When the Monday through Saturday pair wore out, the Sunday pair became the daily, and a new pair was bought for Sunday. Always the same style, though . What we think of as formal today was typically quite casual back in the day.

Esquire, May 1934, shows a combination where modest sneakers are in harmony with a fedora hat.
https://www.thefedoralounge.com/thr...-mens-fashion-1933-1948-by-flanderian.102763/

View attachment 636183

Yes. Sneakers as daily wear, agreed, wasn't a thing, but.... something a lot like the original Vans (first released in 1966, but their take on a style that was decades old at the time) had been around since at least the 30s, and before (there's a reference to canvas tennis shoes in The Great Gatsby, set in 22, written in 25). Mostly worn as Tennis shoes - where I think they got a foothold off the court in part was when they became associated with Resort Wear, the moneyed classes holidaying on the Riviera. I know that's how I wear them - After not owning a pair of sneakers for maybe twenty years, this last Summer or two have been so unbearably hot, I picked up some Vans on sale for wearing when it's just too unbearably hot for real shoes.

I rather doubt that folks will be whispering behind their hands ….. “Oh dear, look at that chap over there, he’s wearing flat shoes and a fedora. Perhaps someone will take the poor fellow aside and help him.“

Wear your hat with whichever shoes you wish, and wear whichever shoes you choose with your hat. I really don’t think it’s that complicated.

Enjoy being probably the only guy in sight wearing a “proper” hat, and forget about the rest.

And that is very much the thing. If you just want to wear a hat, wear what you like and what you think looks good with it. If you want an accurate, period look that's anther thing - in which case old photos and general information on this website are really helpful there.

 

[Juhani]

There were the 50s rebels like Dean, though as best as I can make out it's really the 60s generation than made jeans such a default. To the point where if I wanted to flash my rebel credentials in 2024, jeans would be the very last thing I'd put on.

Such an eye-opening description of decades gone by!

A hundred years ago, people were ready to beat up those who wore a straw hat in the wrong season. And nowadays you can't really rebel with clothes, or maybe the rebellion starts with a fedora.

I wore a South American fedora as a teenager. Back then it was a part of my personal rock 'n' roll rebellion with a dose of "anti-imperialism". It was about identifying with the songs that Paul Simon performed with a group called Urubamba. As an adult, I got my first fedora as a stage costume when my musical hobby included gigging in bars. Then, it was all about feeling connected to old school Jamaican singers.

Perhaps the overall history of style and fashion also reflects how the hat as a piece of clothing and as part of social history has changed in meaning. It's now an individual choice. The reason I referred to the history of fashion was that it was really news to me that Keith Richards wasn't the first to combine a fedora with sports shoes.

As for shoes, I have never owned a pair of sneakers like Vans or Converse in my life. For years, all my shoes were ordinary mass-produced shoes, mainly ugly and cheap, and when they broke, you couldn't fix them.

 

[Edward]

As for shoes, I have never owned a pair of sneakers like Vans or Converse in my life. For years, all my shoes were ordinary mass-produced shoes, mainly ugly and cheap, and when they broke, you couldn't fix them.

Yeah, that's where I gravitated to a solid brogue some years ago. Felt more comfortable to me than a sneaker, and I like that they can be repaired. Stll bugs me with the Vans that they're effective disposable - though TBH this is the third Summer I've had out of my first pair, with a lot of wear, and the others I picked up were all on sale. I'd still rather a decent leather shoe, but some days here in London it's just too damn hot for those. Still, September on Sunday, pleasant weather to come in the next few weeks.