Pulling Off the Casual Look

[ScionPI2005]

I agree with most of what has been said here. Most of my fedoras (both felt and straw) are semi-casual and I consider them hybrids that can be worn with both casual clothes and more formal attire.

I was amazed to find that my recently acquired Stetson Whippet actually looks good with casual clothes and even jeans. However, that may be due to the fact its a nice medium gray color, and has a little bit of a worn look to it.

I also have a thin-ribboned VS custom in natural felt that looks awesome with a pair of blue jeans and a button up shirt tucked in.

However, I do have one rule. If I'm going to wear any kind of t-shirt (and I rarely wear non-collared shirts) I have to go with a flat cap. I just cannot do a fedora with a t-shirt. I'd say the same for shorts, but I never wear them anyway.

 

[Ordinary Guy]

I agree with most of the above....... State of mind is a definate. The more you wear your hat (s) the more you will feel comfortable in them.

Also try match your hat with what you have on . sure you always do with your suits but do it with jeans and sweaters too.......

Real dressy Fedoras have only one place but all the rest can fit in, start doing it and you will get the knack and feel quite comfortable....

Speaking of sweaters with fedoras..

 

[avedwards]

I'd say a sweater is a very versatile piece of clothing. It can be worn with jeans or even shorts, but at the same time it can be worn with a sport coat or (a V-neck sweater) with a suit and tie. It's almost as versatile as the fedora itself.

 

[colps]

I like the hat, the sweater and the landscape,if that is were you live your a very lucky man.

 

[flylot74]

I think that it depend on the fedora. I doubt anyone can get away with a homburg, but I do just fine with my Open Road. It goes well with jeans and a henley shirt, though most of the time I'm in chinos when casual.

In fact, purely by accident I was caught with jeans with wide red braces over an unbleached cotton henley shirt, leather gloves, rough out ropers and my Open Road helping a friend at a feed store. The owner commented that I looked like "a natural"(it's a compliment in west Texas).

I doubt I could have gotten away with it wearing my dark blue or grey "work of Art", but the pale Open Road? Why it just screams working man's hat!

 

[Hatsquad]

Not really.......

Django, surely if you have a vintage coupe you should dress the part by wearing a fedora, a suit and a trenchcoat (cigarette optional )?

Django's coupe is a very cool street rod, methinks, as fitted in the 50's, and therefore his attire is perfect for the hot rod/street rod culture.

Rock on, Django!

Regards, Gerry.

 

[Ordinary Guy]

I like the hat, the sweater and the landscape,if that is were you live your a very lucky man.

It is where I live and Thank You sir..... The landscape is my doing, it is my hobby. The hat is John Penman's doing, and the sweater just seemed right with the hat.....

 

[jpbales]

Due to my lack of formal clothes and money to purchase them with, I always wear casual clothes on a day-to-day basis, the exception being church on Sundays.
I think fedoras go fine with jeans:

especially if you're carrying a huge knife lol

or

And I wear them with t-shirts a lot (though I don't have many good pictures of it)

And of course, straw goes with about anything (except perhaps winter clothes )

 

[Ephraim Tutt]

Looks perfect to me jpb. The fedora is a versatile piece of kit.

And don't you two look happy! Love those smiles.

 

[thunderw21]

I just wear a hat that goes with what I'm wearing. Thin ribbons work well for casual. Depends upon the degree of casual, too. I have several different degrees of casual in the pics below.

 

[Goose.]

I've seen a few pictures of loungers wearing casual attire with their felt hats, how do you all do it? ...[huh]

My mom dresses me funny.

.

 

[Ephraim Tutt]

I gotta say that for a group of folks who pride ourselves on bucking the fashion trend, some of us worry an awful lot about whether we conform to some other folk's ideas of what's fashionable.

Do fedora's work with casual gear? Take a look at the happy hatted folks above.

The old 60's motto applies - 'If it feels good, do it!"

 

[CRH]

I just wear a hat that goes with what I'm wearing. Thin ribbons work well for casual. ...

Excellent choice!

How I yearn for the eyes of a younger man. Peep sights have always been my favorite. I look through a telescope these days .

 

[High Pockets]

Goose buddy, you are one of those guys who can pull off a look that the rest of us only wish we could!


Ephraim Tutt,.... I don't think anyone could have said it better:
"I gotta say that for a group of folks who pride ourselves on bucking the fashion trend, some of us worry an awful lot about whether we conform to some other folk's ideas of what's fashionable."

 

[Torpedo]

Ephraim Tutt,.... I don't think anyone could have said it better:
"I gotta say that for a group of folks who pride ourselves on bucking the fashion trend, some of us worry an awful lot about whether we conform to some other folk's ideas of what's fashionable."

:arated:

This said, I believe the main reason some do not like, or find difficult to get used to, casual clothing with fedoras, is that the modern dressier ensemble (suits or jackets with odd trousers, plus ties or bowties) looks not that different (generally speaking, and note I stress generally speaking, and specially from the average viewer, not the FL viewer) from the Golden Era image; while modern casual ensemble is (generally speaking, again) more distinct as compared with that era.

Hence, a fedora with dressier clothes is taken as more coherent than a fedora with casual clothes, specially with the kind of modern casual clothes that is very different from the "classic" kind; the hat seems to "clash" more.

This is simply a matter of adjustment and adaptation, and of course, a matter of personal taste, too. Some of the casual clothes-cum-fedora I see here in the FL I like, and some I do not, some I believe works for other people, but do not for me.

On my experience, the more confident and used you grow with your hats, the more naturally you will combine them with a wider range of clothing. Or not. ; but as said, it is largely a matter of personal preferences - certainly much more that it is (or should be) a matter of other people preferences... as Ephraim most aptly has summarized.

 

[daizawaguy]

Try first Jeans and a white shirt...that should get you going...

 

[memphislawyer]

Today I wore a camel color wool polo sweater and some dress pants to work and wore my acorn-colored Akubra Stylemaster. A couple of nice hat comments and a couple of Indiana Jones comments. All positive. Because so few nice fedoras are worn, people notice them and they notice that they are not the cheap indy-rocker hats that are popping up. I have worn my Stylemaster with jeans and shorts and khakis.

But remember, you see yourself more critically than others do. they all may think you look fine, and you see yourself as looking dopey. I just wear my hat because I like to, and though I think I look 'better' in my dressy Stetson Saxon in grey, others like the Stylemaster better.

 

[Chuck Bobuck]

My mom dresses me funny.

lol She's dressing you just fine.

 

[dnjan]

Try first Jeans and a white shirt...that should get you going...

And what is wrong with jeans and a white shirt?

Though I often add a brown tweed sportcoat ...

In fact, I think that tweed sportcoats help the transition from business-dress to casual.
And given that the original question was from a lounger in Ontario, he could probably wear tweed sportcoats at least 6 months of the year.

 

[PabloElFlamenco]

I dress funny, too. This awaiting a bus at Paleochora, Kriti, Ellas, frappé within hand's reach...

And if it's not that, it's something else: a trend is ...moderately western clothes (jeans, corduroy, jeans jacket, suede jacket, western shirt, desert boots...) with thin ribbon hat (open roadie or similar).