What to wear with a fedora....

[Socrets]

During the winter, I usually wear a collared shirt of some sort, belt, dark colored jeans or khakis and shoes that match my belt or at least doesn't clash too badly with the belt. Unless you have no regard for dressing for the weather, matching the rest of your clothing shouldn't be too hard. In fact, I think the late fall and winter are seasons where a fedora looks really nice...

 

[Roninjedi]

Hi! New guy in town here. I disagree with the suggestion that a t-shirt is never appropriate with a fedora. I think a clean, solid color, t-shirt paired with nice looking jeans or slacks and decent sneakers can be a stylish yet casual look. You can also pair the t-shirt with a vest or overshirt (Hawaiian, Cuban, or bowling shirt, for example). Now flip flops, raggedy shorts, and an old Budweiser t-shirt probably wouldn't work with any lid other than a baseball cap or a beat-up straw cowboy hat.

Just my opinion. That and .75 cents gets you a Coke.

 

[raven_retro]

If you're trying to revolve your outfit around the hat, just go with the "style" of the hat. It's dressy, so that means you should have a semi-casual feel to the ensemble. Crisp shirts would automatically look great, remember that a lot of classic items are still used today. If you don't have a nice ironed shirt, t-shirts are definitely ok. However, the t-shirt should be a quality one. Heavy weight, cotton or a soft cotton blend with a v-neck in a neutral color (no writing on it or anything!). Denim for the trousers with either shirt option. Try for a medium to dark wash (dark always looks put together) with no rips, tears, or super white whiskers. If the jean is medium wash, a light whisker dresses it up a bit. I think medium wash plain jeans look too casual. You want a boot cut or classic trouser style if possible. Khaki trousers are nice too, but you have to be willing to iron it. For the shoes, a leather dress shoe or leather walking shoe will work. If you want to wear converse make sure they're clean and not grungy looking. Optional accessories could be a loose tie, scarf, or even a vest.

It's all about adding dressy hints (like nice shoes or a smart shirt) to the overall look. T-shirts are ok, just make sure it's not your favorite band shirt or an undershirt. Personally, I find Cubano shirts as a nice compromise between modern and classic.

 

[Not-Bogart13]

I get called on my insistence about a collared shirt often. It's a personal hang-up of mine, and I know it. Adding a vest or overshirt to a t-shirt makes me happy, though.

I do find that smaller brims make for more casual hats, especially straws. But if anyone ever thinks that an outfit is too casual for a fedora, think back to all those old black and white photos from the depression. You know, the ones with five guys in tank top undershirts and old trousers standing around having a smoke next to a pickup truck.

 

[tonyb]

Some guys can pull of unexpected style using clothes that you would not think could look good. Style is a very individual thing. There are safe bets to get one started, but don't be afraid to experiment. Follow your personality and consider the specific hat.
...

What hat wearing can do is help you find an outward mode of self expression, so don't over-think.

NB13 has it right, as usual.

If there's any one universally applicable (almost so, anyway, to be equivocal about it) maxim, it's the old "wear your clothes, don't let your clothes wear you" line.

If you suspect you're looking a tad affected in your hat (or whatever), you probably are. But, you know, it isn't necessarily the attire itself. Once you grow accustomed to wearing a hat, chances are you'll get to feeling a bit odd and out of place without one.

 

[Mulceber]

I like to wear baggy 'repro' levi's and a leather jacket, or a ricky jacket and it really matches a fedora. Even a Dickies Bip-overall with a nice jacket and a striped jailhouse-type T-SHIRTworks for me.. there has to be some colour-coordination in your ensemble matching with the hat. Oh, and for shoes.. workmans-shoes or converse allstars are my favourites..

I agree - I can usually pull off a t-shirt with a fedora as well. It's really more about how you coordinate the colors and how you pull off the look than anything else. -M

 

[memphislawyer]

I say go for it. Tonight, I had on the pants to a blue pin striped suit, no coat, white shirt, red tie, black shoes and in 85 degree weather at 6:45, took out my Stetson Saxon Caribou grey felt hat for its first spin. Immediately upon walking into the restaraunt with my wife, the greeter, a man of about 20 to 22 years, commented favorably on my hat and smiled. Upon leaving, a waitress of about 35 did and the young man made sure to welcome me back. I can not imagine that if you wore a button up shirt and leather shoes with a fedora, someone would not say that looks snazzy. Now with chinos and tennis shoes, it might pass for along the lines of a baseball cap, just another choice of hat, but with dress clothes, or even say chinos and a nice sweater, given the look you try to bring off, someone will comment on it. My wife thinks it is an affectation I have now, trying to find reasons why to wear my hat, but given what happened tonight, well, I am so glad I hit the submit button on my Akubra Stylemaster Acorn today

 

[elvisroe]

For my money it all depends on the hat and what you feel comfortable in. The most important thing is to make sure you don't look like you're playing dress-ups.

Don't let your clothes wear you!

I'm 30(ish) and while I wear a suit to work, I tend to go pretty casual elsewhere.

I agree that a T-Shirt with a tall hat can make you look like a bit of a pencil-neck but a more casual stingy-brim looks fine.

I tend to live in jeans and collared shirts which work well with a hat. When it's cooler I'll match that with a more casual suit/sports jacket or a woolen overcoat when it gets cold. If I'm wearing a sweater or my short trenchcoat I tend to reach for a flat cap.

As Avedwards suggests you don't want to look like you're on your way to a costume party!

 

[Spats McGee]

I get called on my insistence about a collared shirt often. It's a personal hang-up of mine, and I know it. Adding a vest or overshirt to a t-shirt makes me happy, though.

I do find that smaller brims make for more casual hats, especially straws. But if anyone ever thinks that an outfit is too casual for a fedora, think back to all those old black and white photos from the depression. You know, the ones with five guys in tank top undershirts and old trousers standing around having a smoke next to a pickup truck.

NB has pretty squarely hit some of my own thoughts on this. For me, T-shirts are for mowing the yard. I almost never leave the house in a shirt with no collar. Part of that is my job, which already requires me to be in a collared shirt 5 days a week, so that's what I'm used to.

All that really means is that I don't pull off the T-shirt & fedora look. I've been looking at some of the old photos on here recently and it's very interesting to see so many depression-era farmers wearing fedoras. While I tend to think of fedoras as "dress hats," used to be that they were just "hats."

 

[Spats McGee]

I say go for it. Tonight, I had on the pants to a blue pin striped suit, no coat, white shirt, red tie, black shoes and in 85 degree weather at 6:45, took out my Stetson Saxon Caribou grey felt hat for its first spin. Immediately upon walking into the restaraunt with my wife, the greeter, a man of about 20 to 22 years, commented favorably on my hat and smiled. Upon leaving, a waitress of about 35 did and the young man made sure to welcome me back. . . .

:eusa_clap I'm betting that you'll get more favorable comments that unfavorable ones. I know that I do. We do all get the odd stupid comment occasionally, though. That's why we have a "Dumbest Comment I Ever Heard" thread. Glad you didn't get one on the Saxon's first outing.

My wife thinks it is an affectation I have now, trying to find reasons why to wear my hat, but given what happened tonight, well, I am so glad I hit the submit button on my Akubra Stylemaster Acorn today

It may seem like an affectation for a little while, but that will wear off once you feel more accustomed to wearing a fedora regularly. Pretty soon, if you go to meet someone who doesn't know what you look like, you'll be telling them: "You can't miss me. I'll be the guy in the hat."

Oh, and let me help you out. Here are some good reasons to wear a hat:
1) It's raining.
2) It's sunny.
3) It's chilly.
4) It's Tuesday.

 

[jcw122]

Thanks so much everyone for your responses! I've been working on my wardrobe and have found a few looks that I enjoy a lot! I'll have to post photos sometime

 

[The Lark]

I consider a vest over a t-shirt or short sleeve collar to be kind of silly.

That said, I wear my vest with jeans... but they're both dark charcoal colored!

Anyway, that's my basic attire to go with my hat.

 

[suitedcboy]

If you want to see for yourself one great example of casual clothes paired with a fedora see The Lark's avatar. The lark, you look great, fantastic way to pair that fedora with something other than suit n tie.

 

[jpbales]

i'm a college boy too

usually in the cooler months I wear jeans with a t-shirt or polo (I've been wearing Golf shirts lately and they're amazing).
I try to never wear athletic shoes unless I'm actually doing something athletic, so usually I go with leather such as loafers (I have Sperries myself), boots, or some other kind of leather shoe that doesn't look too dressy nor too athletic. Tennis shoes just really destroy your look if you're wearing a fedora, in my opinion, but some people can/do pull it off and it looks fine.
I usually wear a brown/black leather coat, which naturally just looks great with just about any fedora. Plus, if you wear t-shirts, it covers up the t-shirt. I wouldn't be too afraid of wearing t-shirts as long as they don't have giant, cheesy logos or goofy colors or anything. I try to wear t-shirts that fit (aren't oversized) and have solid colors and simple designs.
Don't forget to match your belt to your shoes and don't wear white socks with black shoes, etc. While a hat doesn't necessarily have to match what you wear, I try to keep in mind what the color of the hat matches/contrasts well with and the color of what I'm wearing. If I wear black shoes/belt I may try to wear a black hat or a hat with a black band. Or If I wear a gray shirt I may wear a gray hat. My fiancee taught me to never wear two different patterns, so don't wear camo shorts with a stripped polo shirt lol I always try to go for the solid color polos anyway.
Just be creative and be yourself.
Jimmy

 

[The Lark]

Hey thanks suitedcboy! You look like something out of a film yourself. I want to get hold of a hat like the one in your avatar as well.

Anyway, I guess it ultimately comes down to giving your casuals a sharp cut to match the hat and a bit of color coordination.

Here's what I'm wearing today.

 

[Classified00]

My $.02

Back in the golden era of hat wearing, men didn't dress a certain way because of their hat. They wore whatever clothes were socially popular at the time and topped their outfit off with a nice hat. In other words, a man in 1946 didn't wear a suit because he was wearing a hat. He wore a suit because it was the style at the time for men his age and in his social circle and the hat was an accessory.

I think the same is true today. I wear the clothes that are common for someone my age in my social circle and I top my outfit off with a hat. For me in the summer that means; a polo / short sleeve button down / tee, khaki shorts and athletic shoes. I top that off with a hat (the past few months have been a Dobbs Milan Straw Fedora). In my case, if I removed my hat I would look like everyone else around me. When I don my hat, I still look like everyone else around me but I'm wearing a hat

That being said, I totally understand that someone may dress around their hat because they want to create a certain look (adventurer, wiseguy, traveler, man of means, etc...) but I see that as personal preference not a requirement to wear a hat.

In short, my advice would be "dress the way you normally would, then add a hat".

 

[Gilgamark]

I agree with the advice to remember that fedoras weren't considered dress items during the time they were worn regularly. I wear my hats with whatever I'm wearing.

I remember reading that the advice used to be that a gentleman needed a brown fedora and a gray fedora. That covered him for whatever he was wearing.

 

[Rick Blaine]

Why not...

Diggin' in the garden, I'll wear a panama w/ a wife beater , chinos & work boots, whatever works f/ you.... as has been said; YOU wear the hat, the hat doesn't wear you.

 

[Spats McGee]

. . . . I remember reading that the advice used to be that a gentleman needed a brown fedora and a gray fedora. That covered him for whatever he was wearing.

If you look at the "newbie needs advice" threads here, I think you'll find that it's still the advice given, at least here at the Lounge. I know that I've advised people new to hats to go get a couple of staple hats, a brown and a gray, before venturing off into more exotic colors.

 

[T Rick]

My usual dress is pretty casual. Jeans and T Shirt much of the time, jeans most of the time. Wondering if the "typical" Fedora hat is too dressy for jeans? I often do move to a silk shirt (Nat Nast typically) for evenings out, would the shirt, jeans and a hat work in most folk's opinion?

Any suggestions/recommendations for a good hat to start with (price range under $100, better yet if around $50 so I could get two colors, one for black or blue shirts and one for earth tones). Suggestions?

I did actually just buy my first "Fedora" style hat, but it's not really thought of as one I think. It's a Filson Tin Cloth Packer hat (oil cloth). It's more for inclement weather, and I think may go well with my goatskin A2 (current issue) flight jacket, and be okay for wearing outside in Michigan's Winter.