10 Best Irish Leather Flat Caps for Driving [Newsboy Cabbie Hats]


There are a wide variety of leather flat caps on the market today. Although all of these hats share similarities, leather newsboy caps sit taller on the head and have a more distinguishable bill than flatter, more traditional leather ivy hats. The type and amount of panels can affect the shape of the cap and can affect whether the cap fits loose or snug against your head.

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These are my choices for the best leather flat caps:

I like the Stetson Oily Timber Hat Leather Ivy Cap because the leather is incredibly soft. In my opinion, it is softer to the touch than most other types of leather. It sits comfortably against my head and isn’t stiff like some types of leather can be. Here’s what mine looks like:

leather-flat-cap
leather-flat-cap-stetson-material

Two other brands that I really like a lot are Sterkowski and Bailey of Hollywood. The cool thing about the Sterkowski brand is they have been in business since the early 1900’s, but still to this day they operate as a smaller brand and don’t mass scale their hats. They value handmade, small batch production.

Leather newsboy caps, although often referred to as “flat caps”, have design differences when compared to traditional flat caps. A newsboy cap often has a six or eight-panel design that has a more rounded shape than a flat cap, and sits a bit taller on the head.

Most leather flat caps are designed for fall and winter use. Leather itself is pretty good at insulating warmth, but most of these caps also have a lining to help trap heat. You can also find flat caps that have tuck-away earflaps (like the Sterkowski hat on the list above).

In this article let’s take a closer look at these leather caps so you can find one that fits your specific needs. Let’s also discuss several things to consider when buying flat caps.

My Favorite Leather Flat Cap

Stetson Men’s Oily Timber Leather Ivy Cap

Stetson is a well-known name for hats and caps, and they have a wide variety of leather flat caps to choose from, including leather ivy caps, leather newsboy caps, and leather Irish caps. Stetson was founded in 1865, and has a long-rooted history in making dependable headwear.

I like the Stetson Oily Timber Leather Ivy Cap because the leather is very supple. It sits soft and comfortable against my head and isn’t stiff like some types of leather can be.

I also like the five panel design that accents the three center panels. This specific design allows the cap to sit a bit flatter than other types of six panel hats that have a rounder, taller shape.

Here is what my Stetson Oily Timber Leather Ivy Cap looks like:

leather-flat-cap

This is the current price of this Stetson flat leather driving cap available at Amazon (paid affiliate link takes you to Amazon.com). Here’s what you need to know about this cap:

  • Made with Leather – Yes, this is a leather flat cap. As I mentioned above, mine has a very comfortable feel and isn’t stiff like some types of leather can be. If it very easy to wear.
leather-flat-cap-stetson-material
  • Design – This flat cap has a contoured design made with five panels, with three of the panels being the central focus. Those three middle panels flow from front to back, and help give the cap a flatter shape than other types of 6-panel leather newsboy caps, which have a rounder design.
leather-flat-cap-stetson-front
  • Bill – Yes, this leather driving cap has a small 2 inch bill that is only visible from the front. It is tucked under the paneling, but does provide some weather protection and makes it easier to adjust the cap. The bill is stitched to the upper portion of the cap.
leather-flat-cap-stetson-measure
leather-flat-cap-stetson-lining
  • Lining & Fit – This leather ivy cap has a satin lining. To me, this is a sort of all seasons hat. It’s probably best for spring and fall, but I also wear it on occasion during both the summer and winter months. There is a Stetson accent pin attached to the right side of the cap. This cap has an elastic closure and, in my experience, fits true to size.

Click here to buy this Stetson Oil Timber leather flat cap available at Amazon (paid affiliate link takes you to Amazon.com). In my experience, this cap fit true to size. It is available in S/M sizing, and L/XL sizing.


Other Leather Flap Caps to Consider

Leather Newsboy Caps

Leather newsboy caps, although often referred to as flat caps, are designed a bit different than traditional flat caps. Newsboy caps have a more rounded design, and sit a bit taller on the head than a flat cap. The bill of a newsboy hat usually sticks out a bit more than a flat cap.

If you prefer leather newsboy caps, these are my favorite options:

  • Stetson Weathered Leather Edison Newsboy Cap – This Stetson newsboy cap has an eight-panel design and is made with a weathered leather which gives this cap more of a rugged look. The telescoping back section allows for it to be worn shallow, or pulled down deep onto the head. This cap has snap buttons on the bill which allows you to adjust the way the cap sits. Click here to view this Stetson weathered leather newsboy cap available at Amazon (paid affiliate link takes you to Amazon.com).
  • Bailey of Hollywood Noclin Leather Newsboy Cap – If you don’t like the weathered leather look of the Stetson cap above, this Bailey Noclin cap might be a better option for you. It uses smoother traditional leather, and has a classic rounded eight-panel design. It is fully lined and is best for fall and winter months. It has a deep snug fit that can be pulled down deep onto the head. Click here to view this Bailey of Hollywood Noclin leather cap (paid affiliate link takes you to BaileyHats.com).

Leather Ivy Caps

A leather ivy cap is just another name for a leather flat cap. If you don’t like the Stetson Oily Timber Leather Ivy Cap that I own, here are other nice options for you to consider:

  • Stetson Galway Weathered Leather Ivy CapThis Stetson ivy cap has a classic three-panel design which creates the single-panel look across the top of the head. It is made using weathered leather to give it more of a rugged, rustic look. This cap does have a lining so it is best for fall and winter months. It has a stitched-down 1.5 inch brim that is slightly visible from the front. Click here to view this Stetson weathered leather newsboy cap available at Amazon (paid affiliate link takes you to Amazon.com).
  • Bailey of Hollywood Glasby Leather Ivy CapThis Bailey Taxten ivy cap has a different design than the Stetson cap from above. This cap has a five-panel design, with the large front panel dominating the top of the cap. This cap is made with antiqued lambskin leather. This cap does have a lining so it is best for fall and winter weather. and it has a stitched-down 1.5 inch brim that is slightly visible from the front. Click here to view this Bailey of Hollywood Glasby 5-panel cap (paid affiliate link takes you to BaileyHats.com).

Leather Flat Cap with Earflaps

Perhaps you need a leather ivy cap for cooler weather. It is quite common to find flat caps that have hidden earflaps that tuck into the cap and can be folded down when needed.

Now, these types of earflap hats don’t usually have a lining, and probably won’t be the best optino for extreme cold weather. But these leather earflap hats can help keep your ears warm in mild winter conditions:

  • Sterkowski Leather Ivy Earflap Cap – This Sterkowski leather cap features tuck-away earflaps that can be folded down for cold weather. Yes, this cap is made with genuine leather. Sterkowski has been around since 1926, but has remained as a smaller brand that doesn’t mass scale their products so that they can prioritize care. This cap has a warm cotton lining and features side buckle detailing. Click here to view this Sterkowski leather ivy cap available at Amazon (paid affiliate link takes you to Amazon.com).

5 Things to Consider When Buying Leather Flat Caps

How Should a Flat Cap Fit?

Flat caps should fit snug, but not too tight around the side of the head. The actual fit of the cap itself will vary depending on the paneling and design of the flat cap you choose.

For example, leather newsboy caps have a rounder design that fits a bit looser on the top of the head than traditional flat caps. Some leather flat caps will have a deeper back section that allows the cap to fit deep on the head (for example, Stetson Edison Cap on the list at the top of the page).

If you want to read more about how to size your flat cap, visit this flat cap sizing guide. The main takeaway is that the actual fit of your flat cap will vary and depends greatly on the type of paneling the cap uses. These leather driving caps often fit low on the head.

Why do Flat Caps Have Snap Buttons?

Certain types of flat caps have a button on the bill. Other types of flat caps will just sew the bill to the top of the cap, and this leaves some people wondering, why not sew all flat caps? What role does the button play?

A snap button on top of the bill allows you to adjust the fit of the cap. Some people appreciate the ability to dictate how flat the cap fits across the head, and a snap button helps provide that flexibility and allows the cap to be pulled deeper on the head if needed. To read more, visit my article that explains the purpose of snap buttons on flat caps.

Lined vs Unlined Leather Ivy Caps

Many leather flat caps and leather newsboy caps will have an inner lining, which can help protect the cap from sweat, but also can help trap in extra heat during cold weather. Because leather isn’t very breathable compared to other materials, most people wearing a leather cap are wearing it during the fall and winter months. For hot weather, there will be better options (summer hats).

If you will be wearing your flat cap during cold weather, buying a cap that has an inner lining is a way to add extra warmth. Tuck away earflaps are also a nice addition for winter weather.

Leather Flat Cap Alternatives

Leather is durable and warm, and provides nice weather protection. But what are your other options and how do they compare to leather?

  • Cotton Twill – Cotton twill flat caps are often worn in the warmer summer months. This type of material is usually more breathable than leather, although some types of cotton twill caps may be lined and used for winter.
  • Polyester – Many summer flat caps will be made with breathable polyester material, and may even have ventilation throughout the cap.
  • Linen – Linen is very lightweight and breathable and popular to wear in the hot summer months. To see options, visit our article about the best linen flat caps.
  • Corduroy – Corduroy flat caps are less common, but do exist. This is another nice winter option and might be a nice alternative to leather if you prefer a softer cap. To see options, visit our article about corduroy newsboy caps.
  • Waxed CanvasWaxed Canvas hats are popular because they offer durability and water-resistance. Although there are some types of flat waxed canvas hats, this type of material is more common in bucket hats.

Types of Flat Caps

  • Leather Flat Cap – Leather ivy caps, leather Irish caps, leather cabbie caps, leather Gatsby caps, and leather Scally caps are all essentially the same thing (there may be some minor design differences regarding the shape and number of panels). All of these caps are designed to sit flat on the head and are basically one in the same.
leather-flat-cap
  • Leather Newsboy Cap – Most newsboy hats are designed slightly different than traditional flat caps. Newsboy hats often have a rounded six-panel design that sits a bit taller on the head than a flat cap. The brim is usually more noticeable on a newsboy cap than a flat cap. It’s important to note that flat caps will occasionally be referred to as newsboy caps, so this term can be used loosely at times.
  • Leather Peaky Blinders Cap – Due to the rise in popularity of the show Peaky Blinders, many people often ask what type of hat does the character Thomas Shelby wear in Peaky Blinders? Although many people often refer to it as a flat cap, the cap that the character Thomas Shelby wears in Peaky Blinders is a newsboy cap, not a traditional flat cap.
  • Leather Driving Cap – A leather driving cap can refer to the entire range of leather flat caps, leather ivy caps, and leather newsboy caps (and even other types of hats). Most driving hats have a low-profile design that can fit comfortably in the cab of a car.

Paul Johnson

Paul is a lead content creator for Workwear Command. He has had several blue-collar jobs which have provided him a wide range of experience with tools and gear. He also has a business degree and has spent time in business casual office settings.

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