How To Wear A Driving Cap – 3 Style Rules Every Guy Should Know

by Welcome to Outsons
Wear A Driving Capss

A classic of English history, the Driving cap remains a warm and comfortable choice for men across the globe today.

Depending on where you are it might be known as a flat cap, Scally cap, Bunnet, Dai cap, Paddy cap or even as a Cheese-cutter. Stateside of the atlantic ocean however, it is known as a driving cap – a much more sensible name if you ask us. 

Whatever you choose to call them, driving caps are the perfect accessory for chilly winter days to keep you warm and well-dressed. Compared to many hat choices, a flat cap is softer and less intrusive to incorporate into your look throughout autumn, winter and spring. Not just reserved for driving, the flat cap is perfectly suited for the golf course or a walk through the woods to keep your head warm and dry. They go really well with muted and dark colors, so try pairing them with some brown chukka boots and a navy hunting jacket for a timeless and well-kept aesthetic. If you’re into driving vintage cars, then wear a flat cap with some suitable leather driving gloves for a really classy appearance. 

Flat caps are unstructured, soft, rounded caps with short brims. Flat caps essentially come in two different construction types, one that is made with a single piece of fabric on the top of the hat, and another (commonly referred to as a newsboy cap) that consists of eight triangular panels that meet together at the top underneath a cloth button, similar to a baseball cap in terms of concept. 

The newsboy cap has more volume in the body of the hat, which allows it to sit overlapping around the edges and make the brim appear even slimmer. The name flat cap sometimes only refers to the former style, and newsboy cap to the latter, but the names flat cap and driving cap are now interchangeable and cover a whole base of slightly different constructions. 

Wear A Driving Cap
Image Credit: Film Stories

As the successor to the bonnet, the flat cap came into popular use during the 17th century before aristocracy adopted the style for use in outdoor sports such as shooting and hunting. The name newsboy cap comes from the hats association with newspaper delivery boys, something which has stuck and anchored an historic relationship with the working class. There was even a legal stipulation back in 1571 that any boy over the age of six had to wear one on Sundays and public holidays, or be faced with a fine. This was brought in to help encourage the wool industry and helped cement the flat cap into mens fashion long after the act was repealed 26 years later. 

During the late Nineteenth century, the flat cap made its way into US culture and was worn by school boys and with formalwear before a slight decline in the middle of the century. Interestingly, when the fez was banned in Turkey in 1925, the flat cap saw a spike in popularity which has led to them being the headwear of choice for many men in the region.

In recent years, they’ve been taken up by the likes of David Beckham, Guy Ritchie and Brad Pitt, while the resounding success of Peaky Blinders has increased the popularity of the flat cap even further into a genuine mens hat choice for much of the year. There’s even an official Peaky Blinders brand called Garrison Tailors which is part owned by Steven Knight, the creator of the show and partially by David Beckham too, providing accurately reproduced luxury menswear including suits, coats and plenty of hats. 

Wear A Driving Caps
Image Credit: Cheatsheet

1. Material Matters

Material Matters
Image Credit: Aran Sweater Market

While driver caps come in lots of different fabrics, patterns and colors, you need to be careful when considering your choice of hat. For one, you need to make sure it doesn’t clash with the rest of your outfit. This is especially important if you’re going for a traditional tweed, houndstooth or herringbone. The last thing you want is to have two slightly similar fabrics that end up with your hat throwing your whole outfit off. In this case, we recommend pairing any pattern with a solid block color in the rest of your look in order to avoid this. 

With the changes in trends in modern fashion, there has been a rise in flat caps with patchwork, color-blocking and other kinds of wild looks. While we don’t outright dislike these, we think they’re much better suited to other more eccentric types of hat, and when you’re going for something as classical as a flat cap you should stick to heritage. 

The functional properties of the fabric construction are also a key thing to consider, especially if you’re planning to wear one in cold weather. Wool and cotton are the original choices, helping to give the driver cap some breathability and insulation when needed. We would strongly suggest sticking with natural fabrication over anything synthetic like polyester, or airtight like leather. Flat caps are particularly warm because they essentially create a warm air cushion between the hat and the wearer, but choosing a synthetic material will mean that any sweat from the crown of your head won’t be able to escape. No one wants a sweaty hat. 

2. Keep It In Context 

Keep It In Context
Image Credit: Lacoste

What we mean when we say keep it in context is save your flat cap occasions to those that they were meant for. Save them for the outdoors in the colder months, and don’t try to squeeze it into a summer outfit because it simply won’t suit. Even though there has been a rise in flat cap hats being made from lightweight cottons and linens, we would recommend staying clear of these and saving them for the cold weather, rather than donning one with a T-Shirt and shorts. There are plenty of other hats you can wear in the heat from baseball caps  to beach hats, so opt for one of these instead.  

Aside from the time of year, you also need to keep things straightforward in terms of wear. Don’t wear your flat cap backwards or sideways. You’ll look like you’re a 15-year-old at a school disco, it’s an adult hat style and it deserves to be treated as one. Some versions of the flat cap can be snapped, but this gives off a more feminine appearance and wasn’t part of the original design so again, we’d recommend staying with what we all know works and not trying to change too much.  

3. Use Your Head

Use Your Head
Image Credit: NME

Yes, use your head. Figuratively and literally.

The softness of flat caps is something you can use to your advantage to suit your face and head no matter what shape it is. Play around with the brim a little, but not too much, in order to find out what works best for you. While most flat cap hats come with quite a straight brim, you’re well within your right to give it a bit of a curve. Not as much as you’d expect to find on a baseball cap, but a little bit can go a long way in helping your cap to fit more comfortably on your head and help to shape your face as well. 

It’s mostly common sense when it comes to shopping for newsboy caps. Most big manufacturers of mid-to-low end choices of flat cap will have regular sizing structures such as small, medium and large with diameter ranges for head size so you can get the best fit. Like we said before, the fact that your flat cap is soft structured will help with this and you might get a little stretch, but be sure to follow the brand’s sizing closely. If you’ve got the financial freedom to get a flat cap custom made then you can get it to fit your head size perfectly, and are likely to get great service if you go to a traditional milliner. Too big and you risk looking like a chef who’s lost his kitchen, too small and you’ll look like a weird cartoon character. It should fit pretty similar to a baseball cap, just with some extra fabric on top. 

In terms of brand and branding, you’ll likely want to stick to something from a longstanding company with a minimal look. It all depends on the rest of your wardrobe of course, so consider whether it needs to go with your favourite jacket, golfing outfit or color-match your t-shirt that’s just visible beneath a sweater. The hats themselves can be varying degrees of sporty to smart, so when you wear a flat cap just keep in mind what kind of thing you’re going for. Top brands to look out for when buying a flat cap are Christy’s, Wigens, James Lock & Co. and Bailey Hats. On the sporty side Kangol is the one, thanks LL Cool J.

How To Wear A Driving Cap – 3 Style Rules

To remember how to wear a flat cap, just follow these three simple rules:

  1. Material Matters – choose your fabric, color and pattern carefully 
  2. Keep It In Context – stay within the guidelines of tradition, trust us
  3. Use Your Head – get the right hat size, shape it to suit your face

Feature image: Alpha Coders

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