How do I pull off a casual Fedora?

[bluefoxicy]

I like the Fedora, but it's too classy for jeans/t-shirt or vanilla bizcas. I think some black shoes (not necessarily dress shoes... the NB walking leather shoes I have should work), decent khakis (my Lands End ones have nice, defined line), a good pressed collar shirt with a button neck (not a full button, a polo)...

I think I may actually need an open jacket on top to pull this off, maybe a long one rather than just a waist-length one? Not a trench coat, but maybe just above the knee.

I guess I don't want to look like this guy:



Maybe this guy though... from this link:



Huh, is that a dark flannel jacket?

Anyway, casual Fedora?

[Muirtach]

Unless I am going for a long ride I do not leave the house without either a dress hat or my daily wear fedora. The key is to feel comfortable and having a good quality hat that fits you in both size and style. I generally wear a nice shirt (open collar, not button-down) and slacks (vintage wool when I can). My brother pulls off one with a t-shirt and cargo pants.

[leighton]

Confidence.

[bluefoxicy]

Huh interesting. The style seems to be very... dressy looking. A couple of the guys at the bar I frequent have them, but they're always a bit sharp dressed. I'd think it'd look out of place if you weren't in a certain level of style; but I prefer to avoid the full formal wear style (no suits!).

Hmm, thanks.

[Bobtrumpet]

A straw Fedora might be the better choice over felt, at least during clear weather; it looks a little more casual.

I've been planning on buying a hat or two, and the clothing you describe is what I usually wear. I'm strongly leaning to a straw Fedora for most days and a felt for inclement weather or something a little more formal.

[bluefoxicy]

A straw Fedora might be the better choice over felt, at least during clear weather; it looks a little more casual.

I've been planning on buying a hat or two, and the clothing you describe is what I usually wear. I'm strongly leaning to a straw Fedora for most days and a felt for inclement weather or something a little more formal.

Straw huh?

I know two fellows at the bar that show in Fedoras. One has several; he showed up in this sort of thing recently, but I've seen him with a white band too:



The other has something akin to this:



These are not as dressy as the dude up top on this post with the $41 hat!

[StylinLA]

Confidence.

What he said.

I'm personally not good at wearing my fedoras with casual clothes- but that's just me. I use them when I'm decked out. Sport coat at minimum.

But it all generates from you.

[Argonaut]

A huge peacock feather in the brim would make the hat itself seem casual by comparison.

[Lion71]

People tend to forget that back in the day the fedora was an everyman hat. You could wear one with overalls as easily as a suit. They aren't really dress hats, just hats. If you want a dress hat, get a homburg. If you want a hat you can wear with anything, get a fedora.

Leo

[The Mick]

Like this. Once again I'll state the importance of a light grey with a multi colored band.

[D.Irving79]

Confidence.

people are so insecure.

[heirkb]

Confidence.

Yup.
However there are different types of casual fedoras. There are the ones in your detective picture and there are the kinds that Kangol makes. I prefer the Kangol ones cause they work better with a younger guy look (dark slim denim, nice sneakers not some New Balance running shoes or something, nice sweater or shirt with a bomber style jacket). The Kangol ones are a balance between the old school ones you like and the annoying hipster fedoras that all the stores sell now.
As for your question, I'd suggest a coat that has a similar cut to that trench coat regardless of its length with some khakis like you said. As for shoes, I'd think either something that is intentionally not a dress shoe or a nice brown dress shoe. Nothing with a clunky square toe, but not one of those super pointy modern shoes either since those are really more for guys who are going out at night and wearing jeans in my opinion.
If it's cold enough, I'd suggest a solid collared shirt with a v-neck sweater over it. Perhaps a nice scarf to top it off, or not...and a spray of Blenheim Bouquet underneath it all. I think that'd be pretty classy
People will probably disagree but that's what I think.

[Cuttingboard]

no!!

[MMCCX]

the -right- fedora can be worn with anything, it's a broad term. just think of Indiana Jones, it can be anything from workwear to semi-formal depending on style and materials.

my go-to is an early '60's Saks Fifth Ave fur felt, 1.25" brim with a wide ribbon. dark taupe w/ dark brown ribbon, unbound brim. $12 at Salvation Army, but would likely go for $100-$200 on Ebay. digging around can be fun.

gets plenty of compliments, whether with a white tshirt/jeans/polished shoes or linen pants and a Cuban/guyabera shirt. kids (i'm 40) think it's cool and older people have actually thanked me for wearing a hat (and knowing when to take it off).

my only solid advice would be to stay away from the trendy 'patterns' and get a quality fur-felt (three season) and/or straw (summer).

if you want to be overwhelmed with suggestions and reviews, the B&B of hats is Fedoralounge.com .

[Bertilak]

if you want to be overwhelmed with suggestions and reviews, the B&B of hats is Fedoralounge.com .

The attached screen shot shows what I get. If I try to look in the directory I get:

Forbidden
You don't have permission to access /cgi-bin/ on this server.

[bishop]

As much as I'd like to see fedoras revived in great number, wearing them now seems a bit pretentious. It all depends on the ensemble. I'm not going to offer any advice on what to choose, only that warning. Be careful. The point of great style is not to show off.

[Muirtach]

my only solid advice would be to stay away from the trendy 'patterns' and get a quality fur-felt (three season) and/or straw (summer).

For emphasis. The newer trend to extremely short-brimmed (I wear a short brim, but not quite that short) fabric "fad"oras should be avoided if you are aiming for the classy look.

[mdunn]

Casual fedora wear is all about the jaunty angle

[galopede]

Bob, try this: thefedoralounge