Here’s a trick: if you want to design a kickass flag, start by drawing a one-by-one-and-a half inch rectangle on a piece of paper.

A design at these dimensions held 15 inches from your eye looks about the same as a three-by-five foot flag on a flagpole a hundred feet away.

From left: flags of Chicago and Washington, D.C., as rendered by 99% Invisible producer Avery Trufelman

Your design has to work within that tiny rectangle, because unlike other designed objects, a flag is usually seen at a distance. It is also often in motion and partially obscured.

Credit: hugovk

Given those limitations, it’s surprising how simple and compelling.

Vexillologists — those who study flags — tend to fall into one of two schools of thought. The first is one that focuses on history, category, and usage, and maintains that vexillologists should be scholars and historians of all flags, regardless of their designs.

The other school of vexillology, however, maintains that not all flags are created equal, and that flags can and should be redesigned, and improved.

Ted Kaye of the Portland Flag Association — the largest subnational flag organization in the country — is one such vexillologist. Kaye has a word for these activist vexillologists of his ilk who go out into the world and lobby for more beautiful flags: “vexillonaires.”

Flag of the Portland Flag Association.

You’ll remember from episode #6 that the principles of flag design, according to the North American Vexillological Association, are:

  1. Keep it simple
  2. Use meaningful symbolism
  3. Use two to three basic colors
  4. No lettering or seals of any kind.
  5. Be distinctive

For some reason, cities of the United States seem to have a lot of trouble with principle #4.

The city of Portland, Oregon, didn’t have an official flag until 1969, when a group proposed a flag to the commercial club of portland. Portland’s mayor at the time brought in the Portland Arts Commission, which brought in local graphic designer Doug Lynch to work on the flag. Lynch asked the stakeholders what was important to them in a flag, and also did his own search for powerful visual imagery for the city.

Lynch came up with an abstract flag design, with blue lines representing the Columbia and Williamette rivers, bordered by stripes of gold representing commerce or grain growing along the rivers, all flowing into a white four-pointed star representing the city. The background color, green, represents the forests.

The city council took Lynch’s flag design and plopped a city seal on it. The flag was rarely flown.

Portland’s first city flag. Courtesy of Ted Kaye.

Nearly thirty years later, Doug Lynch, then in his mid-eighties, went to a meeting of the Portland Flag Association. Lynch explained the story of his botched flag to the gathering of vexillologists. At the end of the presentation, Lynch talked all about the changes he wanted to make to the flag (including taking the seal off), and regretted that there was nothing he could do about it.

The vexillologists — nay, vexillonaires — sprang into action. This elite team of historians, manufacturers, and designers agreed to come together on behalf of fixing Portland’s flag. They went to Portland city council and testified on the flag’s behalf. The new/old flag was adopted a week later, and it’s been representing Portland ever since.

Portland’s new and improved city flag

Roman Mars spoke with vexillologist and vexillonaire Ted Kaye at his home in Portland. When Roman arrived, he found that Ted had flown the San Francisco flag in Roman’s honor, because that’s what kind of guy Ted Kaye is.

Credit: Roman Mars
  1. Kevin Winslow

    After finishing this podcast the only thing running through my mind was that 99pi need there own flag. Maybe through a design competition through a site such as 99designs?

  2. Stephanie

    I like the Hundertwasser NZ flag! Probably a little too kicky and not Union-Jack-y enough to get chosen though…

  3. SD

    That same photo (as cover image) appears on Wikipedia and is marked “(seen from back)”.

    1. AJV

      That doesn’t explain it: the green square should still be on top next to the flag pole. The flag really is upside down.

  4. JMS

    Eeww, Sam and Vera, two of the worst mayors Portland has had. I can’t say I’ve ever seen the flag, but now it will only serve as a reminder.

  5. Greg Smith

    Great episode.

    I can’t resist showing off the Scarborough flag here, because it’s awesome… even though Scarborough (a suburb of Toronto) isn’t actually a proper free-standing city anymore:,_Ontario

    The cliffs in the flag are a defining geographic feature, kind of like a scaled-down version of the white cliffs of Dover.

    It’s also neat because it has a strong cohesiveness with the Toronto flag:

    Toronto’s is clever because the white lines suggest the distinctive shape of (new) City Hall, and also form the letter “T”.

    Maybe the prominent maple leaf in both of these flags is a bit on-the-nose, but hey.

  6. I live in Durham, North Carolina, and I love our city flag. Not only is it bright and distinguishable at a distance, it’s mainly displayed in a cool vertical format:,_North_Carolina#mediaviewer/File:Flag_of_Durham,_North_Carolina.svg

    “The City Flag was created by designer Al Nichols who was the winner of a flag contest held by the City of Durham. The simple, yet bold flag communicates the “New Spirit” of Durham.

    “The flag’s colors represent the following:

    Royal Blue – courage
    Red – action and progress
    Gold – high quality in all growth
    White – high ideals

    “The Seven Stars on Durham’s city flag are symbolic of the New Spirit of Durham in seven areas:
    the arts, commerce and industry; education; medicine, human relations; sports and recreation, and the preservation of Durham’s rich heritage. Also Durham’s birthday, April 26th, is under the constellation of Taurus, The Bull. A cluster of seven stars is located on the shoulder of the bull and is called the “Seven Sisters” or the Pleiades in Taurus.”

    1. Vatnos

      I love Durham’s flag too! One of my favorite flags in the country. Sadly, Chapel Hill and especially Raleigh have pretty bad flags (not a fan of NC’s either but I doubt it will ever change… it never has). I hope to see these cities put some effort into their flags in the future. Having a good flag can be a source of civic pride, for cities like Chicago and Washington DC.

    1. Brian

      Oh, you’re in Boise as well? I agree, the flag for the City of Trees isn’t all that great.

  7. Janey Skinner

    The South African flag is, to my eye, exceptionally beautiful – and it uses more than 3 colors.

    1. I agree with regard to South Africa’s flag. I would call these sensible guidelines rather than rules. And aside from having six colors, it follows the other guidelines in being simple yet distinctive.

  8. Roman, while Maryland’s flag doesn’t follow many of the basic rules for good flag design, it’s incredibly captivating and easily recognizable. What are your thoughts?

  9. Katrina

    City of Toronto flag… Follows the rules and looking good! If you’re not familiar with Toronto the shapes represent both the shape of New City Hall and the letter T.

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