Flat Cap Guide – How To Pick A Newsboy Cap – Gentleman’s Gazette

Learn to pull off the newspaper boy cap here: https://gentl.mn/flat-cap-guide

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So first of all, what is a flat cap or a newsboy cap?
Obviously, I’m wearing one here right now and it’s made out of a woven fabric. It’s not knitted, there’s no felt, like in typical menswear hats, overall, it has a very level and trim silhouette based on the one-piece construction, meaning, the top is made out of one piece of fabric and then you have seams on the side to get the distinct shape.

Another characteristic is that the body off the top part of the hat is pulled over the brim. Generally, it’s either sewn on or snapped on, that way, you get a triangular side profile that gives the hat its characteristic shape.

Over the years, the flat cap has gotten many monikers so it’s known as newsboy cap, cabbie, gatsby, IV, Jeff, duffer, duckbill, driving, you name it. If you want to learn all about the monikers, please check out the guide on our website here.

So how do you wear a flat cap? First of all, if you get something made out of tweed just the way I’m wearing it here right now, you always will make sure you have a certain amount of contrast between the fabric on your hat and the rest of your outfit.

Definitely, avoid flat caps that are very similar in color but not the same because that just looks off; it’s like pairing a navy suit with a black pair of pants. Second of all, do shape the brim to your taste; that means you can actually move it like this and to curve it a little bit, you can tilt your hat and get the exact look you want.

Don’t wear your flat cap backwards because it just looks awkward. This is not a baseball hat, after all, it is more stylish brother.

Four, don’t worry a flat cap in the summer because it simply makes you overheat and sweat and it’s unnecessary.

Five, don’t wear a flat cap unsnapped. Sometimes, you’ll find flat caps that can be unflapped, however, that’s a style that’s usually associated with women in the 70s.

So how should you buy a flat cap? First of all, it’s important that it fits comfortably on your head.

The flat cap was originally made from tweed by the wool fabrics or sometimes even cotton and that reason you should stick with those materials. In my opinion, tweed is really the best material because it has the depth of color, it keeps you warm, it’s hard wearing, and it’s just a wonderful fabric. To learn more about tweed, please check out our in-depth tweed guide, here.

Sometimes, I’ve also seen denim caps or maybe leather caps or faux leather ones. I personally don’t think it’s a very advantageous look and I’d rather stick with the classic stuff. For that same reason, I stay away from patchwork flat hats or multi-pattern caps because they’re simply too loud. Just like a bold red or really loud blue and green hat. The good thing about tweed is usually it comes in more subdued colors that suit the fall-winter season. At the same time, the color composition of the fabric is comprised of a range of different ones so it’s very easy to combine it with other items in your wardrobe even though they don’t match and contrast. So whenever you find flat caps that are either too bold or come in small, medium, and large, I suggest you skip them unless you know that they will fit you and that you’ll like to wear them and they won’t just be a fashion item that you have to throw away after a season. if you want to learn more about flat caps and what brands you might want to buy please check out our full guide on the website here.

Last but not least, if you think a flat cap makes you look dated just browse the Internet and look for pictures of David Beckham or people like Brad Pitt which are obviously mainstream media celebrities and they can still pull it off and do so on a regular basis.
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RJ Stug says:

can some one please tell me the reasoning behind the design if any? why the droopy front part? i cant find an answer.

Ishraq Haider says:

4:07 your pants look rather baggy. yes i know you don’t wear slim fit, but just compare it to your jacket. your jacket is a decent fit (not slim) but your pants are more on the relaxed side

Kohlio says:

I always liked the look of these caps, I just never thought I would look good in one.

William Lucas says:

The red gloves are ridiculous like some sort of priest.

MaximusPayne says:

These definitely are not fit for summer, but what stylish option is there for hot weather? Baseball caps are not an option…

thisislen says:

He looks a bit like paul mccartney in the thumbnail

Scott Phillips says:

It’s not 1935 you can’t wear these anymore

silversurfer12371 says:

Good job once again. Thank you for this video.

colomblanco says:

It’s a nice hat if you’re a European farmer

Rafael Corujo says:

Thank You…

Jay Jackson says:

I agree that these are classic and dapper but for some reason I have never liked the look of them. Nice video though.

Jake Boss says:

is there a video you can direct me to on how to dress it down while wearing the ivy flat cap? like a tshirt, jeans or shorts? or could you do a video on this in the future?

Alex says:

specks = neps

Chintamani Helekar says:

By the order of peaky fukken blinders!

Hayden Huynh says:

What’s the song that you use for your intro? 🙂

Joseph Steele says:

Fuck me what am i watching

Michael Ossmann says:

First of all, thank you for your helpful and instructive videos. However, how to avoid messy hair when taking the hat / flat cap off your head? E.g. when you do a pompadour or a side parting with Pomade.

Thank you.

cava1962 says:

HI, Like always GREAT…..Hermosas Chaquetas & Lovely Boinas………..

jbird Perez says:

what’s up my koOl brother…

adamscott says:

You can’t beat a good flat cap

Paul Rivera says:

If these are hats that can be worn in the cold season, show hats that are good for summer, and spring.

Brad Dumon says:

I bought my “flat cap” last year in Edinburgh, Scotland.  I love it.

Waldemar says:

Both my grandfather and great grandfather wore these hats, though they weren’t as taught/sleek looking as yours.

Crash Bandicoot says:

My dad is a janitor about to retire, came to America in 1972 and he has always worn flat caps.

Shotbytim says:

You said not to wear a flat cap in the summer and for wool, that absolutely makes sense, but what about linen or poplin?

MitchelMestrini says:

Recently bought my own gatsby flat cap, and I’m in my twenties. Some friends are saying I look much older and other people are complimenting my new style. I personally love the cap!

KAC3 says:

What do you think of the motorcycle caps?

Jax Wins says:


Gijs Oomkes says:

First of all thanks for another informative video. Lately you have been speaking faster and faster (especially in the intro’s) and sometimes it’s really hard to follow everything you say. Since you are trying to get information across to an (international) audience, this might be something to pay more attention to while filming. Thanks!

Jamesthacoolcat99 says:

Nice video. I dont wear hats very often i think when i start it will be a fedora. Your chukkas were awesome. Also the double breasted windowpane suit at the end was very sharp.

Bushcraft on Horseback says:

Also my favorite cap! I think everyone looks better in a newspaper boy cap.

Deadly Duddly says:

None of the caps this guy wears in the video are Newsboys ? They are flat caps but not Newsboys , a Newsboy must have a eight panel construction and a button on top .

zaco21 says:

I don’t like this particular flat cap that you’re wearing but I’ve seen others that I like. You could mix them with a jeans jacket, blouse of jumper to make it more casual. Smart look. How about a video about hat maintenance?

Henry V of England Heir of France says:

I wear flat cap with crew neck shirt and zipped hoody…looks really casual but honourable.

C.S.H says:

im just here because of blinders

Future says:

I’m glad these are coming back in style. It’s the only style of hat I’ve ever had.

Cyc0Dud3 says:

while a lined tweed cap would indeed be too warm for summer, an unlined linen flat cap is great for warmer weather. it keeps the sun off of my balding head and out of my eyes!

also, two manufacturers i’ll vouch for: herman headwear from italy and lawrence & foster from england! custom tailored; check them out: https://www.youtube.com/watch?v=V_uq4n5dLxk

Chris Norton says:

How to wear a flat cap. Step 1 don’t

saleem waheed says:

Been wearing these hats my whole life. We called them Cool caps and Jeffs back in the day. I have some madras ones from King Ralph that are really nice, and compliment my summer outfits. I have a denim one that I think looks good with work wear. But my favorite might be the waxed canvas model from Barbour. Wow I could go on and on.

Cap't Jack says:

How do I install the razor blades?

spoofmisters says:

I really want a Newsboy Cap, with pannels. However I live in Australia and rarely ever gets cold enough for that Winter Style. Anyway you think this cap could work in warmer weather, or simply too hot?

Phy Hendyranathoth says:

Would have been easier to watch if it didn’t have that annoying drum beat going on in the background.

Rubin Begeja says:

I’m curious which is the right kind of cap for men with long hair?

Benjamin Harrison Gray says:

That’s my usual. 8 panel, chocolate suede leather. Mine’s passed down from my Welsh great grandfather.

Steven Ward says:

I have a couple of Hanna Hats and absolutely love them

Waltski says:

Great video.  Very informative.  I like the caps as they do not hit the ceiling of my car as I am driving.  They also make a distinct fashion statement.

Cool One says:

Completely disagree with the video’s advice to never wear a flat cap backwards. Flatcaps worn backwards are casual, sporty, hip, and commonly worn by everyone from Samuel L Jackson to Jonny Depp to Brad Pitt. It’s a legit way to sport a flat cap.

양승현 says:


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