For a big city, Boston is kind of short.

Yes, we’ve got our elegant blue-glass John Hancock Tower — or 200 Clarendon, since the insurance giant moved out — which soars 790 feet above Copley Square. When it was built 40 years ago, the Hancock became the tallest building in New England.

It still is.

Close by, there’s the blocky Prudential Center, which was the tallest US building outside New York City when it opened in 1964.

Beyond that, the crop of towers in the Financial District wouldn’t stand out on most big-city skylines, never mind something to rival Dubai’s Burj Khalifa — the tallest structure in the world at a dizzying 2,716 feet. Indeed, Boston is even bested by places like Cleveland, Indianapolis, and Oklahoma City. Yes, Oklahoma City, where the Devon Energy Center has 50 feet on the Hancock.

In all, there are 67 buildings in the United States that are taller than anything in Boston. Several impressive towers are in the works, but none will come close to topping the Hancock. Los Angeles, Chicago, and San Francisco will all build towers far taller than ours this decade.

So why is Boston so height-challenged? Here’s the tall and short of it:

In many ways, Boston’s current — and future — skyline is governed by its past. When the 125-foot Haddon Hall went up on Berkeley Street in 1894, appalled neighbors responded by pushing for a cap of 70 feet on new buildings in the Back Bay. And for most of the first half of the 20th century, while New York and Chicago built skyscrapers, zoning rules downtown prevented anything above 125 feet. That kept Boston’s skyline dominated by church steeples, just as it was during Colonial times. The lone exception was the 496-foot Custom House Tower, exempt from local zoning because it was a federal building.

Those rules really shaped the city from the 1890s until the 1950s,” said Brendan Carroll, director of intelligence at real estate firm Perry Brokerage Associates.

Then came the era of master planning in the 1960s — when the Prudential Center rose to far overshadow the Custom House Tower. The concept of a “high spine” in the Back Bay was born and office towers began to sprout downtown. Still, many Bostonians have come to love the relatively modest scale of the city’s neighborhoods. That affection surfaces every time someone proposes a building of substantial height. Invariably, issues like shadows and wind are raised.

“Our neighborhoods, from the North End to the Back Bay to the South End, are full of people who love living in what appears to be a 19th-century community,” said Robert Brown, managing director at architecture firm Perkins+Will. “To them, tall buildings mean more density, more parking, more shadow.”

There also are higher powers at work. Like the Federal Aviation Administration. Logan Airport’s proximity to downtown has capped the height of buildings in the economic heart of the city.

In 2008, Massport — which operates Logan — and the FAA outlined height limits of 600 t0 800 feet in the Financial District, to keep clear takeoff paths from runways that sit just 2 miles across Boston Harbor. While the airport’s proximity to downtown has helped boost job growth in downtown Boston, it has put a lid on what can be built in that part of town.

The FAA restrictions quashed the 1,000-foot Winthrop Square skyscraper that then-mayor Thomas Menino called for in 2006, and forced Millennium Partners to scale back the tower it’s now planning for the site, from 775 to 690 feet. A hard cap of 275 feet in the Seaport — just across the harbor from the airport — is one reason everything in Boston’s newest neighborhood is so squat, and why Boston’s tallest buildings sit further afield, in the Back Bay.

“There are only certain places in the city where you can actually build very tall,” said architect Gary Johnson, a principal at Cambridge Seven Associates, who keeps the Massport height map on his desk. “You have to navigate around all these flight paths.”

Throw in state laws governing shadows cast on Boston Common and the Public Garden, and environmental regulations that have long precluded building towers along the downtown waterfront, and potential sites for something like Menino’s dream building become even scarcer.

Once a building tops 600 or 700 feet in height, construction costs begin to rapidly rise, making the economics tricky, even in a booming real estate market. The materials and engineering expertise needed to build safely at that height don’t come cheap, and extra elevator shafts are needed to efficiently transport tenants up to all those floors, consuming rentable square footage.

“It just all gets more expensive,” Perkin+Will’s Brown said. “So the rent you need to command is equally high.”

In addition, the demand for an office in the sky isn’t what it used to be. Big banks, law firms, and other traditional skyscraper tenants have been squeezing into less square footage in recent years, while the tech companies driving Boston’s market often prefer to be closer to the street. That has kept rents at the very top of office towers relatively flat.

“The original Boston skyscrapers were office buildings, and many still are,” said Johnson, the Cambridge Seven architect. “Today it seems the demand for tall office buildings is not quite so strong, at least locally.”

But it’s stronger for condominiums. Johnson co-designed One Dalton, which when complete will be Boston’s third-tallest building, and entirely residential, with luxury condos atop a Four Seasons Hotel. Millennium Tower, too, is fully residential, while mixed-use towers at South Station and Winthrop Square will devote their top floors — the real moneymakers — to condos and stick office space below.

That makes sense, said Perry Brokerage’s Carroll. If a company wants to pay extra for primo space, it has to justify that decision to its board. But if a CEO wants to drop millions for a condo with an expensive view? That’s a personal choice.

“It’s passion,” he said. “It’s not a business decision.”

Maybe. Architects and developers generally agree that many parts of the city have become more open to the prospect of added height in recent years. There’s intense demand to live and work in the core of Boston, and that means building up, not out. The current generation of 600-foot towers could inspire a new generation of 800-foot towers in the next real estate cycle.

The trick to building high is finding the right spot on the ground, said Tom O’Brien, a veteran developer who’s starting construction on a pair of towers atop the Government Center Garage — the taller of which will hit 528 feet, the maximum allowed by zoning along the Rose Fitzgerald Kennedy Greenway. O’Brien points to the Back Bay — already home to Boston’s three tallest buildings — as the most likely location for something taller than the Hancock, though there would be pricey complications.

“The most obvious scenarios are building over the Mass. Pike,” said O’Brien, noting the opportunity — but also the cost — of constructing a deck over the busy highway. “Of course, there you’d need height to generate the economics to make it work.”

Even there, on the city’s so-called High Spine, height can be a challenge.

It was the expense and complication of building above the Pike that finally scuttled a long-planned 625-foot tower planned above Copley Place in 2016. And when developer Weiner Ventures proposed a 586-foot-tall condo a few blocks west on Boylston Street near Massachusetts Avenue, neighbors pushed back, concerned about shadows it would cast. So Weiner proposed a shorter building of 544 feet that last month was approved by the Boston Planning & Development Agency, almost without objection. One agency board member, Ted Landsmark, even had second thoughts as he looked at a model of the building incorporated into the existing skyline.

“Now that I see it in context,” Landsmark said, “I wish it was taller.”