Reviewed & updated: March 28, 2023 by Jamie Wilson BA
It’s safe to say we all love a style of hat that can truly stand the test of time.
As weird as it would be to see anyone walking around the streets of 2020 in a top hat, a newsboy cap still looks as cool as they have over the last 400 years. Thanks to the likes of David Beckham, we still can’t get enough of flat caps alike.
The question of how to style newsboy caps can be a tricky one to try and answer. With so much choice and so much opportunity, it can feel difficult to get the look absolutely right.
But fear not – we’ve put together a list of three easy, go-to looks for any men looking to pull off a newsboy hat.
Why Wear A Newsboy Cap?
The newsboy cap style has been noticeably popular from the early 1900s, and was something that was born out of necessity. Signifying the kind of guy who will always do whatever he wants, a newsboy cap – or a paperboy hat – can be seen on the workers of the 1920s back to the rappers of the 1990s.
Unlike a baseball cap, newsboys caps still have a visor but aren’t contained by the traditional hat brim, making it more comfortable to wear while still keeping some kind of hat structure. Traditionally made from tweed or wool, the cap has the flexibility to keep your head warm in winter but extremely cool in summer – the ultimate versatility.
Like David Beckham and his newsboy cap collection, many Hollywood stars are also known to wear one, such as Jason Statham. To get this look, try an all-neutral palette against a darker colored cap to really make it shine. Wear a rollneck, smart tailored trousers with a long camel coat and leather gloves for the full-on, old school gangster feel.
Newsboy Or Flat Cap – Is There A Difference?
Newsboy caps can be difficult to identify as they go by so many different names, including a jeff cap, driving cap and a flat cap. Technically speaking, there is a difference between the two hats which can be hard to spot.
A newsboy cap will have an overall look that is a little baggier or looser because of how it is sewn together, while a flat cap will have a slimmer and tighter fit – almost like the look of a piece of pizza. That being said, nowadays the names for the flat cap style are completely interchangeable and over time have developed a shared meaning.
Flat Cap Top Tips
Before we begin to think about ideas for your newsboy cap look, there are some basic rules on how to wear a flat cap that can be applied to any look you choose to go for.
When looking to buy pageboy hats, remember that the classic fabrics will be more comfortable and more breathable to wear. Hats in tweed, wool and cotton will serve you better for longer as well as having better insulation.
Don’t be afraid to shape the flat cap brim with your hands to make it more your own and frame your face. Keep other accessories simple to make sure your flat cap stays the star of the show, working best with bow ties and braces.
Like the classic fabric choices, be aware of the season – newsboy caps made from linen and cotton are best for spring, while caps made from tweed are perfect for winter. The cap lining is also another thing to watch as we want it to be as soft as possible – an italian flat cap will be best for this.
What About The Right Size?
To ensure you wear the right size of your cap, the brim needs to be able to sit comfortably on the forehead. We want our cap to seem as if it is baggy, but still provides a study fit underneath.
Grab the nearest tape measure and start by measuring the circumference of your head, making sure the tape measure goes around the middle of your forehead and is slightly above the ear. When recording the measurement, make sure you check the sizing charts of different brands separately, as no two hats ever fit the same.
Peaky Blinders Realness
We just can’t talk about newsboy caps without mentioning Peaky Blinders. The Victorian look is now something everyone is looking to recreate, and is also a look that works extremely well on many men.
Back in those days, hats and caps alike were built to be heavy and robust, something that now won’t work as well if you’re looking for a spring look alternative. To look like a true Peaky Blinder in your flat cap, keep things simple with a vintage touch, swapping color for more earthy tones.
Mixing and matching texture, pattern and print is at the heart of this kind of outfit, with newsboy caps completing a simple yet chic silhouette. Wear one with a plain white shirt and tailored pants instead of adding a cap to a three-piece suit so your styling looks elegant, not novelty.
Italian Summer Chic
Picture it – you’re on the Italian riviera with a cool beer in one hand and adjusting your flat cap with the other. Flat caps don’t just have to be for an overcast day in the city, but are also one for the ultimate sophisticated summer vibes.
A flat cap is no stranger to the fashion world, making many appearances at various trade shows for men around the world. Particularly in Italy, hats are a staple centrepiece of the trade show trend scene, always questioning how to make a hat ‘like new’ once again.
The real beauty of a flat is that it can work with absolutely any kind of outfit styling. If you’re not up for wearing jeans, try the baseball styling from back in the 1990s, with oversized jackets and wider fitting pants to match the bagginess of your driver hat. Keep to one color or a simple, stripped-back palette to not overpower the impact of the flat cap itself.
If you’re after a more traditional summer outfit, wear your flat cap with some tight fitting jeans and an open shirt. You can take your caps even more casual with a t-shirt and chinos with a long fitting cardigan for some extra warmth. Flat caps look at their best when they are casual, and it’s clear that this cap style is one that a lot of men love.
Wrapped Up In (News)Paper
It’s common knowledge that the flat cap is the perfect winter accessory, looking great when caps are paired with a large winter coat and thicker gloves. Flat caps really suit outfit layering, meaning there is a lot of room for experimentation when it comes to your winter flat cap look.
One thing to bear in mind when styling your flat cap for winter is that your hat will look better if you keep to a simple colour scheme of greys or browns, perhaps adding a pop of colour elsewhere in the outfit to keep things broken up. Ideal winter accessories for caps include understated scarves and leather gloves to stay in-keeping with the classic tradition of the flat cap.
It’s worth mentioning that there are some circumstances where it may not be the most appropriate to wear newsboy hats at all. In more formal settings, it’s not advised to pair it with a really fancy suit for a really fancy occasion. Striking the balance between your newsboy outfit being smart without being too formal is essential, keeping things refined while steering clear of not being able to make the two styles marry.
The How To Wear A Newsboy Cap Debrief
If you’re looking to ditch the baseball cap in favour of something more timeless, flat caps may be your perfect answer.
It’s a style of hat that suits all men but to wear it is a bit of an art form. Making sure you start with the driving hats basics – material, fabric, lining – will mean your cap can easily be paired with anything you want to.
Flat caps work for both casual and smarter outfits but it’s important to remember to keep styling simple and subtle, looking like you’ve put minimal effort in for maximum effect. Whether you opt for the Peaky Blinders feel or dressed-down chic, cab hats will always be a classic headpiece to fall back on.