BEST CITY FLAGS
symbolism hidden within that simplicity. The four red six-pointed stars represent historic events that have occurred during Chicago's history: its establishment as Fort Dearborn; the Great Fire of 1871; the first World's Fair to be held in Chicago (1893); and the second World's Fair to be held in Chicago (1933-34). The two light blue lines above and below the stars represent the two branches of the Chicago River. Bonus points for using a lighter shade of blue than is seen on most red, white and blue flags in the U.S. While some city flags are never seen or beyond being on a flag pole outside city hall, a bank or school, you see Chicago's flag often whenever you visit the city. It's sold at gift shops and hawked by street vendors and used by Chicago natives all over the country to represent their home town. A classic, simple yet symbolic flag, Chicago's flag is also less offensive than any Cubs or Blackhawks gear. (I kid!)
10 (tie). Pittsburgh, PA (adopted 1899) - First of all, I have to be honest. I've always been a sucker for black and gold. Maybe it's because those were my high school colors or maybe it's because those are Mizzou's colors. Regardless, I've always liked the combination of black and gold. 
Pittsburgh's flag, which is black and gold, features a portion of the city's seal - which, itself features a nod to the coat of arms of the city's namesake, William Pitt - at the center. It helped established black and gold as the official color's of Pittsburgh, which has, in turn, influenced all of the city's sports teams (Pirates, Penguins and Steelers) to utilize black and gold as their color schemes. Whereas most U.S. cities rely on some combination of red, white and blue on their flags, Pittsburgh's choice of black and gold makes it stand out from the crowd and helps tie the whole city color scheme together unlike any other city in the country.
10 (tie). Baltimore, MD (adopted 1915) - Yes, another black and gold entry. The flag features 
the Battle Monument at the center on the Calvert family colors, which also make up half of the Maryland state flag. As that state flag made my list of the top 5 best, it stands to reason that a city flag that borrows from it would like rate highly as well. It's different from any other city flag and its combination of a symbol that represents the city and a pattern that pays homage to the state flag gives it high marks.
9. Orlando, FL (adopted 2017) - The newest entry on our list, Orlando's flag gets points for both its symbolism and simplicity. The prominent "O" obviously stands for Orlando, but it also doubles as the 
sun and sunlight over waves, a nice nod to the copious amounts of water in and around Orlando. The O surrounds a representation of the Lake Eola fountain, a prominent local symbol. It also gets kudos for replacing Orlando's previous hideous, too busy city flag. That flag, shown at right, was first introduced in 1980 and its designs screams early 1980s computer graphics. Seriously, it's as if some guy 
designed it on his Commodore 64. The people who decided to dump that tacky old flag in favor of something much cleaner and simple yet symbolic deserves an all-expenses paid trip to Disney World which, thankfully, is nowhere to be found on either flag.
8. Indianapolis, IN (adopted 1963) - I'll be honest. Before starting this project, I was familiar with very few of these city flags. As I did my research, I was disappointed by some of the lousy flags that some really cool cities had, while I was pleasantly surprised by others. And, in other cases, I was pleasantly surprised by both the city AND the flag. When most people think of Indiana, they likely think of the movie "Hoosiers" - small towns, corn fields and basketball. While that is certainly a big 
part of the mythology of Indiana, did you know it is also the 17th most populous state with more than 6.7 million residents? Likewise, did you know that Indianapolis - the state capital and largest city - is the 17th largest city in the country, with a population of more than 875,000? The last time I visited Indy, I was quite impressed with its downtown, which included multiple sports facilities, some cool neighborhoods and quite a bit of shopping, including a mall that spans multiple downtown buildings via skywalks. The heart of Indy is the Soldiers' and Sailors' monument and Monument Circle in the middle of downtown. And the Indianapolis flag plays tribute to that by representing the monument and the circle with the star and circle in the middle of the flag. In addition, the four white stripes leading up to the circle represent the four main thoroughfares (East and West Market Streets and North and South Meridian Streets) that radiate outward from Monument Circle. It's a simple but effective and neat tribute to a city that's a lot more cosmopolitan than many folks think or expect.
7. Portland, OR (adopted 1969) - When you think of the Pacific Northwest, what colors pop into your
head? Probably green for the lush hills and forests and blue for the numerous bodies of water and copious amounts of rain that cause the hills to be so lush. As such, it makes perfect sense for those colors to be featured so prominently on Portland's flag. Officially, the green background represents the forests of the city, the blue represents the Willamette and Columbia Rivers come together near Portland. They threw in some yellow to represent the agriculture and commerce present in the area with a white, four pointed star to represent the city itself and its location amidst all of it. All together, the green, blue, yellow and white make an appealing twist on the prototypical Nordic cross that appears on many flags. The flags are frequently featured and waved at Portland Timbers MLS games and the teams colors are a nod to the flag's colors as well.
6. Chicago, IL (initially adopted 1917; additional stars added in 1933 and 1939) - The Windy City's flag is, at first glance, very simple and straightforward. However, like all good flags, there is some
5. Corpus Christi, TX (adopted 1955) - Texas is a big state with a huge population and a lot of big cities. Whereas the state flag is one of the best in the country (as evidenced by its #3 ranking on my aforementioned state flag list), most of the city flags in Texas are lame. Some red, some white, some 
blue and a star in the middle. Seriously, Dallas, Houston, San Antonio, Lubbock, Arlington, Plano and El Paso all have at least three of the four listed items in their flags. One big Texas city, though, decided to mix it up and do something a little different: Corpus Christi. While there's some blue on the flag, it's a lighter shade of blue, representing the waters of Corpus Christi Bay. While there are stars on the flag, there are eight of them, all representing the city's eight major industries. Best of all, there's a large seagull at the center of the flag, likewise paying tribute to the local beaches and shoreline. It's a unique flag that stands out from the boring, boilerplate flags waving over most large cities in the Lone Star State.
4. St. Petersburg, FL (adopted 1983) - The Tampa Bay metropolitan area is made up of a number of cities, the two largest of which are Tampa and St. Petersburg. While those two cities are side-by-side and serve as anchors to the 18th largest metropolitan area in the U.S., they are light years apart in the 
quality of their city flags. While Tampa's flag is atrocious (more on that later), St. Pete's is terrific. Full disclosure: I'm a sucker for pelicans. When we take vacations to the beach, I love watching the pelicans glide just above the surface of the water and then fly and dive for food. St. Pete's flag prominently displays a pelican at the center of its flag. Behind the pelican are an array of horizontal color stripes, each representing different aspects of life in St. Pete: red and orange for the sunshine and sunsets, green for land, blue for the waters of Tampa Bay and the Gulf of Mexico. It's different, colorful and catchy, yet simple. And, like I said, it has a pelican on it and pelicans are awesome and a great representation of the area where pelicans are endemic and where they often congregate.
3. Denver, CO (adopted 1926) - Colorado is a beautiful state and they've smartly stayed with one of the best license plates in the country: green and white outlines of mountains. In the same vein, Denver's flag is a simple but very effective nod to the Rocky Mountains that rise just to the west of the city. The 
red and white zig zags represent the Rockies, while the blue and yellow represent the sun high in those brilliant blue Colorado skies. Is it pretty basic? Yes. It is kind of obvious? Also yes. However, the simple symbolism is what makes it so good. My only beef is the use of red and white for the mountains rather than, say, green and white. Nevertheless, Denver's flag is simple, clean and symbolic. Everybody can tell at first glance what the graphic represents, which sets it apart from most city flags.
2. Phoenix, AZ (adopted 1990) - Prior to beginning this project, I had no idea that Phoenix had such a great flag. There's not a lot to it and the flag is better for it. It is simply a white phoenix on a maroon 
background. But the use of maroon sets it apart from most flags that stick with primary colors. The stylized phoenix comes from the city's seal but rather than taking the whole seal and slapping it on the flag with the words "City of Phoenix" included, they wisely just took the graphic and reversed the colors. One more bit of trivia on the choice of maroon for the color of the flag (and the city seal): in Greek, "phoenix" means purple. So by using both the phoenix graphic and the maroon color, they are doubly playing tribute to the city's name and the legends surrounding the mythological bird.
1. St. Louis, MO (adopted 1964) - Yeah, yeah, yeah. This is a homer pick, right? Maybe a little bit. But considering that St. Louis's flag won the 2020 March Madness of Flags contest on Twitter as the best city flag in the world (beating out flags from Barbados, Stuttgart, and Yaroslavl Oblast in the Final Four), it makes sense that it tops our list of best city flags in the U.S. The blue and while squiggly lines represent the confluence of the Mississippi and Missouri Rivers that occurs at St. Louis. The yellow
bezant with the fleur-de-lis on it is a nod to St. Louis's French heritage and background of the city. Over the past decade or so, the St. Louis flag has become a more prominent part of the St. Louis area landscape, appearing on hats and shirts available at stores all across the metro area. It was also a prominent part of the symbolism used by the MLS-to-STL efforts to get St. Louis a new MLS expansion soccer team. The flag is even included on the back inside collar of the jerseys worn by the St. Louis Blues. St. Louis as a community suffers from a long and storied history of poor self esteem and self loathing, so its nice to know that we can at least boast that we have a great city flag. (On the other hand, please don't bring up our unfortunate #1 rankings in the homicides and STDs.)
So, there you have our top city flags. Now that we've seen the cities that have done a good job of developing top notch flags, now it is time to turn our attention to the cities the dropped the metaphorical ball and have lousy flags.
WORST CITY FLAGS
10. Springfield, IL (adopted 1917) - Let's face it, Springfield is about as generic of a city name as you can get. Virtually every state has one; there's a reason why "Springfield" was the city name used in The Simpsons. So, if you're going to have a boring, too common city name, you should at least have a 
unique flag. Instead, Springfield, IL has this generic flag that looks like something designed by a middle schooler in an "Intro to Computer Design" class. The stars aren't too bad, but what is up with including their generic font used for "Springfield Illinois" and why is there no comma between those two words? Seriously, Springfield is the state capital and home to the Abraham Lincoln museum and library, as well as his tomb. There are a variety of things unique to the city that COULD have been placed on their flag, instead of this rudimentary design. The best possible design, though, would have been a line of mug shots of all of the Illinois governors who have subsequently done time in prison.
9. Springfield, MO (adopted 1938) - One state over - and about 4.5 hours to the southwest - is another Springfield that has another bad city flag. Red, white and blue? Check. Stars? Check? Needlessly including the city's name? Check. And, like Springfield, Illinois, they elected to leave off the 
comma between the city and the state. Springfield has some cool nicknames ("Queen City of the Ozarks," "Birthplace of Route 66") so you'd think they could have come up with something better than this incredibly dull flag. However, there may be hope on the horizon! There has been a recent movement among Springfield residents to dump their current flag in place of something more unique. Here's hoping that more creative minds prevail and they do just that!
8. New Haven, CT - The easiest and laziest way to design a city or a state flag is to take the seal of the city or state and slap it on a solid colored flag. As discussed in my state flag blog post, a majority of states have taken that lazy - and boring - route. Many cities have done the same. But of all of the cities 
to have done so, few have been so lazy as to do that along with an absence of colors. That's right - New Haven's flag is just the city seal in black on a white flag. It's the most basic and boring thing you can do. From a distance, you probably wouldn't be able to tell if the replaced the flag with a Fruit of the Loom undershirt, label side out. Even worse, the seal has a bunch of Latin words on it that have absolutely no meaning to anyone anymore. As the home of Yale University and a city that's a stone's throw from Long Island Sound, you'd think some bright Ivy League minds could come up with something better than this.
7. Kansas City, MO (adopted 1992) - Over the past few years, I've spent a lot of time in Kansas City for work. KCMO - yes it's in Missouri, despite what President Trump apparently thought after the Chief won the Super Bowl - has some very neat areas. Country Club Plaza is a picturesque shopping and entertainment area while the Power & Light District has helped revive Kansas City's once sagging 
downtown. The city is known as the "City of Fountains" and rightly so, as it features an array of fountains all over the city. So, incorporating said fountains on the city flag makes perfect sense. And if they had just done that on some sort of colored background, they wouldn't be on this list. But instead of sticking with something simple and classy, they had to junk it up with a bunch of words and the oh so predictable inclusion of red, white and blue. Even worse, they couldn't even decide on which city slogan to use, so they threw "Heart of the Nation" on there in addition to "City of Fountains." And then, because I guess they feared that people couldn't discern the city based upon those two hints, they went ahead and added "Kansas City Missouri" to the flag as well. The result is a muddled mess instead of what could have been a great flag.
6. Boston, MA (adopted 1917) - You could make the argument that this one is not a bad at New Haven's - since it at least has SOME color - and that they should be flipped. However, I'm rating this one as WORSE than New Haven's because it's friggin' BOSTON, people! Boston is one of the neatest, 
most historic cities in the country. It played an integral part in the early years of the country. But instead of a flag that pays tribute to that legacy, we get the lazy "seal on a bedsheet" approach. Even worse, it includes a bunch of Latin words that I'm pretty sure that no one from Southie understands. I mean, you've got Paul Revere and Old North Church. You've got Bunker Hill. You've got the Boston Tea Party. The U.S.S. Constitution. The Charles River. You've got so many historic and important possibilities and this is the best they came up with? I do NOT like them apples!
5. Detroit, MI (adopted 1948; last modified 2000) - This is an example of a flag trying to do too much. It has the city seal in the center. The lower left panel (white with gold fleur-de-lis) is supposed to represent France, from where the city's original settlers hailed. The upper right panel (red with gold 
lions) is supposed to represent England, which controlled the city during the latter part of the 18th century. I'm actually okay with those. But then the other two quarter panels (upper left and lower right) and the thirteen stars and stripes representing the thirteen original colonies. Of which Detroit wasn't a part. So, that part doesn't make much sense. Throw it all together and it just seems like a jumbled mess - like they put a bunch of symbols in a blender, hit start and then removed the lid. The symbols flew out an hit the ceiling and that's what they ran with.
4. Cleveland, OH (adopted 1896) - Another rust belt city with a lousy flag. As we've already established words, dates and slogans do not belong on flags. Cleveland's flag unfortunately has all three, along with some random symbols that are supposed to represent the city's industry but the are 
largely indiscernible without an explanation. From a distance, it just looks like a red, white and blue flag with a bunch of jumbled gibberish in the middle. Similar to Kansas City's flag, it's too predictable and too cluttered. Considering this is one of the oldest flags on our list, it's a little surprising that some enterprising mind or designer hasn't tried to come up with something better. I'm not suggesting Chief Wahoo and the Cuyahoga River on fire, but pretty much anything else would be an upgrade over what they have now.
3. Tucson, AZ (adopted 1953) - Whereas Phoenix did a city flag the right way - clean and simple, using a color not usually found on flags- Tucson, the second largest city in Arizona - went the opposite way. Their flag is the oh so predictable city seal on a white flag...or the Southwest version of New Haven. However, what makes this one worse is that the city seal is very busy. On a stationary seal, it may work. But on a flag, from a distance, it just looks like a muddled mess. It's supposed to be a 
contrast between the modern city with its skyscrapers and office buildings and the historic mission that served as the original foundation of the city. But one half is black and white, while the other half is in color. The two representations of the city or contained within the outline of a sun, which - for some reason has different rays on the "modern" part of the seal than on the "historic" part of the seal. Then they throw in a random rope that I guess is supposed to tie it altogether but just serves to throw another color and additional muddling to the logo in the center of the flag. What the should have done is something simple but significant: a green Saguaro cactus next to a yellow or orange sun - a nod to nearby Saguaro National Park and the copious amounts of sun the area receives. Put that on crimson flag and you'd have one of the best city flags out there, instead of this eyesore.
2. Milwaukee, WI (adopted 1954) - Holy cow, this flag is bad. It has everything you DON'T want on a flag. Words. Check. Date. Check. A whole bunch of symbols and pictures of random things. Check. To make matters even worse, some of the items on the flag don't even exist anymore - like County 
Stadium. The designer tried to do waaaaay too much with the flag - pay tribute to Lake Michigan, the brewing industry, skyline, sports facilities, churches, and it ends up being a cluttered, muddled, mess. To illustrate how ridiculous Milwaukee's flag is, here is the description of the flag on Wikipedia: "It displays symbols of Milwaukee on a medium blue background, with the city name below all the elements in Copperplate Gothic. In the center, a gear, representing industry, bears symbols of Milwaukee's identity and history. An Indian head, resembling the Milwaukee Braves logo at the time,[1] represents Native American origins. A flag with two stars, said to be a Civil War-era flag, may also represent a service flag.[3][4] A lamp symbol in the upper right was once associated with the Milwaukee City Library.[1] Below this is Milwaukee City Hall, representing government, which is flanked by abstract outlines of a church, housing, a factory, the Milwaukee Arena, and the former County Stadium (demolished in 2001) along a straight shoreline with waves representing Lake Michigan. The golden barley stalk on the left represents Milwaukee's brewing history, and the red ship with water symbolizes Milwaukee's status as a port city, with the 1846 date of city incorporation from the merger with Byron Kilbourn's Kilbourntown and Solomon Juneau's Juneautown on the flag's right vertically." Whew. That's just a lot of mumbo jumbo explanation and when it takes that long to describe the supposed symbolism of your flag, it's easier just to admit that your flag blows. Thankfully, many Milwaukeeans have realized their flag stinks and there has been a recent push to replace it with something simpler. Here's hoping those more creative minds prevail. In the interim, might I suggest the Brewers' MB ball-in-glove logo, the Bucks' deer head logo and a beer stein? What would be a better representation of Milwaukee than that? Although, let's be honest, almost ANYTHING is better than what they have now.
1. Tampa, FL (adopted 1930) - Those of you who were paying attention to my comments on St. Petersburg's flag were probably able to deduce that the flag of their neighbor, Tampa, would be ranked as the worst city flag. This flag is so terrible, I don't know where to start. First of all, it's not a quadrilateral flag; it's almost more a pennant than a flag. But that's not the bad part. Just look at it! It is supposed to hold all kinds of symbolism when, in reality, it looks more like a subway system map 
than anything else. Or, as one website put it, "this flag would make a great beach towel or a colorful cape for a Floridian super hero." The red and gold section is supposed to represent Spain, while the green, white and red portion at the end is supposed to represent Italy. The red, white and blue sections - and there are a bunch of them - are supposed to represent some combination of France, England and the USA. It's like the vexillogical version of a DNA test that tells most of us that we're mutts that are a result of repeated crossbreeding over the centuries. And, to top it off, they took the oh-so-predictable step of slapping the city seal in the middle, which features a random boat about which there is disagreement as to whether is represents a pirate ship or a tribute to one of its early pioneers, Henry Plant. As I stated earlier, it looks more like a public transit map than anything else. Compare the flag posted above with the diagrams below: the first is a map of the Bay Area Rapid Transit (BART) system in the San Francisco Bay Area. The second is a 
map of the MBTA subway system in Boston. Tell me there aren't some similarities between these and Tampa's flag! Whereas St. Petersburg makes the Tampa Bay area proud with a great, flag symbolism a bird native to the area, Tampa's flag is just a garish, colorful mess. Going back to the earlier analysis that the flag would
make a great cape for a Floridia super hero and given the penchant for crazy, oddball internet stories to inevitably begin with "Florida Man...", just think of the possibilities! It 
could be an adult version of Captain Underpants! Given how terrible this flag is, it's not surprising that many Tampa residents don't even realize they have a flag and when they do, they hate it. A 2019 article in the Tampa Bay Times reported that many longtime Tampa residents state that they "couldn't pick our flag out of a lineup" and that a whopping 92% of people who participated in a survey about the flag said they supported changing it. When your flag is so bad that locals don't even know it exists and, once they do, they overwhelmingly want to change it, you know you have the very definition of a terrible flag. As such, it should be no surprise that Tampa's flag ranks as my worst city flag.
There you have The Golden Rules's list of the best and worst city flags. I hope you found it entertaining - and maybe even a little educational.
Thanks for reading!
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