How to Wear Flat Caps: An EveryMan’s Ultimate Guide

Kingston Lim
4 min readMar 5, 2018

Most of you when you think of hats probably conjure up a thought of a baseball cap.

While there is nothing wrong with supporting your alma mater (go Wolf Pack!), there is a time and place for it. One of those places is certainly not in the work setting where you’re trying to develop and further your career.

Even if you were to wear a logo-less baseball cap in a neutral color, would you wear it when going into an interview? My guess is probably not (unless you’re getting drafted by the NBA, in which case never-mind!).

For those of us that have other endeavors besides playing pro sports, an alternative is needed. And therefore learning how to wear flat caps in both casual and more professional settings is needed.

Besides flatcaps, a fedora might come to mind when thinking of an alternative to a casual baseball cap. It is indeed an excellent choice when wearing a suit. Some would go so far as to say it can be even worn with t-shirt and jeans to “dress it up.” This type of look however, is more of a trendy look that (in my opinion) looks more hipster than stylish.

Some examples of how to wear a fedora, #2 and #4 are more of a traditional look while #1 and #3 are what I call “hipster.”

Unless you are wearing at least a blazer or sport coat, it is not recommended to be wearing a fedora hat unless you want to peacock (nothing wrong with that if its your thing of course).

Today we are looking for an upgrade, not a complete makeover. Therefore to bridge the gap of ultra casual baseball cap and ultra formal fedora, we have:

The Flatcap!

A flatcap is a rounded hat with a stiff brim in the front and is also known as an ivy cap (not to be mistaken with the Newsboy). Because of its smaller shape then the newsboy, its going to have a sleeker appearance.

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The flatcap is both stylish and functional it performs the same functions of the baseball cap and it is a step up in the food chain.

  • A flatcap has the front brim to keep the sun out of your eyes.
  • It has the same usage of keeping the sun off the top of your head.
  • Therefore it keeps you cool during the summer and warm during the winter.

In addition to meeting or beating the functionality of a baseball cap, it has increased versatility by having the ability to be dressed up or dressed down.

In spectrum of hats, the flatcap is business casual piece in the modern sense. Conceptually it is similar to the blazer. Both can be worn to dress up a casual outfit (t-shirt and jeans) and dress down a formal outfit (3-piece suit) as can be seen in the images on the top left and top right respectively.

We would recommend wearing a flatcap that is in a neutral color (gray or brown) as it is the most versatile. Keep the patterns simplistic, either no pattern , herringbone or something similar:

An example of the herringbone pattern.

Flatcaps are usually associated with the Fall/Winter seasons. But there are flatcaps designed more for the Spring/Summers months as well.

As a rule of thumb, light colors are for Spring/Summer and darker colors are for Fall/Winter.

The Takeaway: A baseball cap just won’t cut it in the professional world. Instead, reach for a happy medium between the fedora and baseball cap that can be had with a flatcap. It can be dressed up and dressed down. Because it is both stylish and functional, it should be a core piece of a man looking to upgrade his wardrobe.

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