City Flags That Outshine Their Countries: What Chicago, Amsterdam, and the City of London Got Right

Walk into any tattoo parlor in Chicago on a Saturday afternoon and flip through the flash book. Somewhere between the roses and the skulls, you'll find the city flag. Two blue stripes, four red stars, clean white field. It's one of the most-requested designs in the city, a distinction no state flag and precious few national flags will ever claim.

Now here's the paradox. Most city flags are terrible. They're clip-art disasters stuffed with illegible seals, committee-approved blandness, and color palettes that could put you to sleep. Yet a small number of municipal flags have pulled off something extraordinary. They've become more recognizable, more beloved, and more culturally embedded than the national banners flying above them.

This piece examines three cities that cracked the code: Chicago, Amsterdam, and the City of London. Their success builds a broader argument about what separates transcendent flag design from bureaucratic wallpaper. The thesis is simple. Great city flags succeed not because of top-down mandate but because they follow timeless design principles that invite grassroots adoption.

A Sea of Forgettable Seals

Let's start with the problem.

Roman Mars's 2015 TED talk, "Why city flags may be the worst-designed thing you've never noticed," pulled back the curtain on municipal flag design. It's been viewed over 7 million times, and for good reason. The examples he showed were brutal. Milwaukee's old flag looked like someone had lost a fight with a clipart folder. It crammed a gear, a ship, a Native American chief, a church, a barley sheaf, and a lake scene into a single frame, all surrounded by a circular seal. Pocatello, Idaho, earned the distinction of being voted the worst city flag in North America by the North American Vexillological Association (NAVA). Its old design featured a trademark symbol. On a flag. San Francisco, a city synonymous with visual culture, flew a seal-on-a-bedsheet for decades.

Why does this keep happening? Because flags are typically designed by committees, approved by bureaucrats, and burdened with the impulse to cram in every possible symbol of local identity. The library board wants a book. The port authority wants a ship. The historical society wants a date. The result is a design that tries to say everything and says nothing.

Ted Kaye's guide "Good Flag, Bad Flag," published by NAVA, lays out five principles for effective flag design:

Most city flags violate all five. Against this bleak landscape, though, a few cities got it spectacularly right.

Chicago: The Flag That Became a Civic Tattoo

Chicago's flag is, by any measure, one of the greatest pieces of municipal design in the world.

Two pale blue horizontal stripes represent Lake Michigan and the Chicago River. Between them, on a white field, sit four six-pointed red stars. Each star commemorates a defining event in the city's history: Fort Dearborn, the Great Chicago Fire of 1871, the 1893 World's Columbian Exposition, and the 1933 Century of Progress Exposition. That's it. Three colors, two types of elements, and a story you could tell to a stranger on the L train in thirty seconds.

The flag was created in 1917 by Wallace Rice, a poet and municipal design advocate who won a competition judged by the Municipal Flag Commission. Rice explicitly rejected the seal-on-a-bedsheet approach. He argued for simplicity and symbolism over encyclopedic inclusion, and the commission listened.

A century later, his design is everywhere. Coffee mugs, bar signs, murals, album covers, stickers on laptops, patches on jackets. And yes, tattoos. Lots and lots of tattoos. Chicago's flag is one of the most tattooed civic symbols on the planet. No other American city flag comes close to this level of organic, citizen-driven adoption.

Why does it work? Score it against the five NAVA principles and it hits a perfect five for five. A child could draw it from memory. Each element carries specific, concrete meaning. The color palette is distinctive without being garish. There's no lettering, no seal, no fine print. And you will never confuse it with another city's flag.

The adoption happened bottom-up. Nobody mandated that Chicagoans plaster their flag on everything. People claimed it because it gave them something worth claiming. During sports championships, during moments of community solidarity, during crisis, the flag became shorthand for "this is my city." That's not a branding exercise. That's genuine cultural identity.

Amsterdam: When a City Flag Becomes a Global Brand

Now fly about 4,000 miles east.

Amsterdam's flag features three white Saint Andrew's crosses arranged vertically on a black stripe, flanked by red panels. The design derives from the coat of arms of the noble Persijn family and dates to at least the 16th century, though the triple-cross motif may originate even earlier.

But here's where it gets interesting. Those three crosses, rendered as "XXX," have transcended their heraldic origins to become one of the most recognizable city brands on Earth. You'll find them on the Amsterdammertje, those iconic reddish-brown bollards that line the city's streets. They appear on the official city logo. They were featured on the giant "I amsterdam" sculptures that stood at Museumplein. They show up on everything from government letterhead to nightclub flyers.

And yes, we should address the elephant in the room. Three X's. The red-light district. The association with adult content ratings. Amsterdam hasn't run from this double entendre. It has leaned into the ambiguity, and that decision has only amplified the symbol's memorability and global reach. There's a lesson in that: a symbol with a little edge sticks in the mind far longer than one designed to offend nobody.

Compare it to the Dutch national flag.

The Netherlands' red-white-blue tricolor is respected, sure. But it's generic. Squint and you could confuse it with Luxembourg, Paraguay, or France rotated sideways. Amsterdam's flag suffers no such confusion. Those three crosses are Amsterdam and nothing else.

The design lesson here is about adaptability. A great flag becomes a brand asset that works at any scale, in any medium, and in any context. Amsterdam's crosses function on a bollard, on a website favicon, on a 50-foot banner, and on a beer coaster. That kind of versatility is rare, and it flows directly from the simplicity of the original design.

The City of London: Heraldic Authority Older Than the Nation

Time for a crucial distinction that trips up almost everyone. The City of London is not London. The City of London is the historic Square Mile, the ancient financial district at the heart of the metropolis. It has its own government (the City of London Corporation), its own police force, its own Lord Mayor, and its own ancient flag. Greater London, the sprawling city of 9 million people, is something else entirely.

The City of London's flag features a St George's Cross (red on white) with the sword of Saint Paul, a red upward-pointing dagger, in the upper-left canton. The design dates to at least the 14th century and possibly earlier.

That sword does a lot of heavy lifting, symbolically speaking. It represents Saint Paul, the patron saint of London, whose cathedral has dominated the Square Mile's skyline for centuries. But it also commemorates Sir William Walworth, the Lord Mayor who stabbed the rebel leader Wat Tyler during the Peasants' Revolt of 1381. One symbol, two stories, and both of them vivid. This is the opposite of vague corporate symbolism. This is a flag that points to a specific saint and a specific act of violence.

The City of London's arms are among the oldest continuously used civic arms in the world. They predate the formal establishment of England's own heraldic traditions. Nearly 800 years of unbroken use gives the flag a weight that no redesign committee could manufacture.

Now consider the comparison with the Union Jack.

The UK's national flag is itself a masterpiece, a layered composite of three crosses representing England, Scotland, and Ireland. But the City of London's flag arguably carries more concentrated historical weight per square inch. It represents a political entity that has maintained continuous self-governance since before the Magna Carta. That's a staggering claim, and the flag wears it well.

The Design Principles That Unite These Three

Step back and look at Chicago, Amsterdam, and the City of London side by side. Despite coming from different continents, centuries, and design traditions, they share a common DNA.

Simplicity and reproducibility. All three flags could be drawn accurately from memory by a person with no artistic training. This is the single most important factor in flag adoption. A flag that people can't reproduce informally will never be adopted organically. Think about it: when was the last time you saw someone doodle their state flag on a napkin?

Symbolism with specificity. Each flag's elements tell a concrete story. Chicago's stars mark specific historical events. Amsterdam's crosses trace to a specific noble family. London's sword points to a specific saint and a specific killing. Compare this to the vague symbolism you see on most city flags, where "the blue represents our commitment to water" or "the green symbolizes growth and opportunity." Specificity is what gives a symbol texture and staying power.

Restraint in color and element count. Chicago uses three colors and two types of elements. Amsterdam uses three colors and one repeating motif. London uses two colors and two elements. None of them tries to be everything to everyone. That restraint is the hardest design decision and the most important.

Distinctiveness. None of these flags could be confused with another city's or country's flag. They occupy unique visual territory, and that uniqueness is what allows them to function as identity markers.

Emotional resonance beyond officialdom. This is the ultimate test. Do civilians voluntarily display it? All three of these flags are worn, tattooed, merchandised, and hung from apartment windows by citizens who feel genuine ownership over the symbol. Nobody told them to do this. They wanted to.

What Other Cities Are Learning

The good news? Other cities are paying attention.

Inspired by Roman Mars and the NAVA principles, a wave of municipal flag redesigns has swept across North America in the 2010s and 2020s. Pocatello, Idaho replaced its infamous worst-in-class flag in 2017 with a clean mountain-and-compass design. Provo, Utah swapped out its outdated banner in 2015. And Milwaukee, home of that cluttered collage we mentioned earlier, adopted a dramatically improved flag in 2022 after a public design competition. The new Milwaukee flag features a single golden geometric sun over a blue field. Clean, bold, memorable.

The stakes go beyond aesthetics. A good city flag becomes a tool for civic identity and unity. It gives residents a visual shorthand for belonging, especially in diverse cities where other identity markers might be divisive. A flag is one of the few things everyone in a city shares regardless of neighborhood, background, or political leaning.

But there's a danger in the reform process itself. Even well-intentioned redesigns fail when the process prioritizes inclusion of every stakeholder's pet symbol over coherent design. The lesson from Chicago, Amsterdam, and London is clear: restraint is the whole game. The best flag is not the one that includes the most. It's the one that excludes the most and still tells a true story.

Here's a challenge. Look up your own city's flag right now. Evaluate it against those five NAVA principles. Odds are strong that you've never seen it before. And honestly? That's the most damning indictment of its design you could ask for.

The Tattoo Test

Let's go back to that tattoo parlor in Chicago.

The reason nobody is lining up to get Milwaukee's old flag or Pocatello's former design inked on their forearm isn't because those cities lack civic pride. It's because those flags failed the fundamental test of design. They were too complicated to remember, too generic to mean anything, and too cluttered to stand alone.

Chicago, Amsterdam, and the City of London prove the alternative. When a flag is simple enough to remember, specific enough to mean something, and distinctive enough to stand on its own, it stops being a piece of government-issued fabric and becomes a living symbol that citizens claim as their own.

The best city flags don't represent a place. They become the place, in the minds of the people who live there and the world that recognizes them.

That's a design achievement most nations would envy.