BOSTON—Nothing sticks out quite like a new building in an old city. It can be subtle, like the difference between brick, stone, or plaster that has been weathered, exposed to air pollution—in contrast with that which is clean and new. But new architecture can also be more radical: very often neighboring new buildings are made with different materials and constructed using new methods.

Similarly, even when flawed architecture is not falling into the same old problems—for being out of scale or made out of stained, crumbling concrete, for example—the quality of urbanism is still lacking. When people notice new design, it either seems too forced and inauthentic, or completely absent, as in the case of many suburban landscapes.

“It goes back to Jane Jacobs,” says David Andreozzi, an architect and president of the New England chapter of the Institute for Classical Architecture and Art. “The importance of a house or a piece of architecture, relates to the entire community. Her argument is that a single individual streetscape in New York is like a smile and the minute you lose one tooth, that tooth needs to be replaced. What happens is that street ends up getting eroded from that one tooth if that building’s not replaced . . .”

“Rot sets in,” says Eric Daum, a fellow architect and board member of the New England ICAA chapter. Andreozzi agrees: “Then, all of a sudden that street starts to go down and that street relates to another street and so, in a way, you look at architecture as part of that urban fabric. To have organization through design on a larger level keeps a city alive, just like we’re looking at it on a more finite level.”

These issues are present in many cities, but are more apparent in older ones. In Boston, for example, the traditional neighborhoods, such as Beacon Hill or the North End, rub shoulders with the results of typical post-World War II urban renewal schemes. The West End is now a grouping of towers in a park and the brutalist Government Center, as well as the pseudo-historicism of Quincy Market.

Across the Fort Point Channel from Downtown Boston is the city’s newest neighborhood, the Seaport District. Most of its buildings were constructed in the last 20 years and as such typify contemporary modernist architecture and urban design. Glass and steel towers soar skywards from the waterfront in a variety of angles and curves made possible by computer-aided design. The Seaport’s buildings do not form a street wall, but are surrounded by “green space.” Burnished chrome and milled aluminum, bright LED lights, and the signage of international corporations reward developers with high rents—and developers can even afford to build on expensive sites, create landfill, and endure Boston’s lengthy bureaucratic delays. Still, the combined approach makes the Seaport pedestrian feel that he is akin to an ant wandering through the Apple Store.

The ants can work there; they can rent apartments or buy condos there; they can go to the movies; they can get expensive drinks in outrageously loud restaurants; they can visit a contemporary art museum or enjoy sponsored programming in assorted civic and cultural venues. However, they cannot send their children to school there and until this year they couldn’t go grocery shopping there. Getting around is also difficult, since the neighborhood largely lacks transit and the wide streets encourage fast driving.

At left, the brutalist Boston City Hall overlooking the landmark Faneuil Hall. At right, the new Seaport District (Wikimedia Commons / Raymond Forbes/Stocksy)

The Seaport presents a palpable contrast to the North End, which is perhaps the closest thing to a medieval city that exists in the United States: streets are narrow and tangled. Just about anywhere there was space to put up a building, one was put up. Now primarily residential with a lot of restaurants, in previous days the North End was part of Boston’s port, with warehouses and other industrial facilities. Nowadays the warehouses and wharves are condos. But the streets remain packed with people and the cannolis continue to be delicious.

Despite lacking amenities like grocery stores or much in the way of a mixture of uses beyond its residential and restaurant milieu, the North End is still full of vitality that is unmatched in the region. Curiously, even on streets that are empty of people or are now purely residential, the sense of place, of living, remains.

“For two thousand years the language of classicism was the common architectural language of the Western world, and it was adapted and modified as required, as building program needs determined, or as local building methodologies were adapted to classicism,” Daum says. “So these buildings all sort of worked together with a common vocabulary, but they addressed local and temporal differences.”

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For these sympathetic urbanists, an enduring mystery remains: why are modern people unable to produce humane architecture and urban environments, even when they do little but imitate the past and should benefit from today’s knowledge and technology? At least some new technologies are enabling researchers to examine how people interact with their cities empirically. One group doing this kind of work is Create Streets, based in the United Kingdom. Founding director Nicholas Boys Smith says that he started the organization because he was unsatisfied with the results of planning in London.

“Lots of urbanists in the UK, lots of architects in the UK, argue that all that matters is density,” Boys Smith says, explaining how good streets are essential. “This is an ‘and’ feature, not an ‘or’ feature.”

Create Streets’s research showed that the way a building looks matters to people. Symmetry was the most important design element, according to their research. Also important is what’s known as fine-grained urbanism, where storefronts and facades change quickly and vary as one walks by them. “The things that seem to matter are variety and vitality,” Boys Smith says. “Materials seem to matter a lot. Shiny materials are disliked.”

The ICAA’s Daum says that the work of researcher and architect Ann Sussman has shown that people need a visually stimulating environment. Sussman’s ideas are based on studying the unconscious eye movements of people looking at buildings (or pictures of buildings). Her key insight is something salespeople and advertisers have known for years: people respond to faces and smiling. Interestingly, the architectural term “facade” derives from the word “face.”

“We’re looking for fine detail, which is a projection of greater detail and I think this is all somehow tied to fractal geometry,” he explains. “People can look at a building and by the choices the designer makes in determining what was omitted, what was added and also the other kinds of ornament which can be deeply symbolic, whether they represent for instance, fertility or the harvest or death—all the things that we human beings have to deal with. That potential for symbolism exists within classical architecture and it doesn’t in modern architecture.”

Create Streets also works with Sussman, although Boys Smith says their interest is more on symmetry than faces. “Our brains do appreciate some level of complexity,” he says.

Writing in Aeon in 2015, psychologist Colin Ellard came to the same conclusion. He conducted experiments in New York City where people wore devices to monitor physiological signs of alertness and answered questions about their emotional states. Next to a blank facade, people were bored and miserable; next to a more lively one, they were happier and more stimulated.

“The real risks of bad design might lie less in unhappy streets filled with unmotivated pedestrians, and more in the amassing of a population of urban citizens with epidemic levels of boredom,” Ellard wrote. “Now the reason for the dismal recordings of happiness and arousal in participants standing in front of blank facades is clear. At a psychological level, these constructions fail us because we are biologically disposed to favor locations defined by complexity, interest, and the passing of messages of one kind or another.”

“Architecture, especially on an urban, downtown level, is for the people,” Andreozzi says. “It’s not for artistic individual expression.”

He adds that there were architects deliberately designing buildings to scare people, throw them off guard, and debate everything that’s wrong with society. “That’s a very egotistical, offensive thing,” Andreozzi says. “That’s why I think the majority of that work will be replaced within a hundred years.”

According to Daum, the deconstructivist architect Peter Eisenman decided in the 1980s that the threat of nuclear war meant there was no point to building anything rational.

“We’re destroying our world by creating spaces that no one wishes to be in,” Daum says. “If you work in traditional styles and are working in a traditional cityscape, you don’t have to be a great architect to make a building fit in and which contributes to the whole. But if you’re a mediocre architect and you do a modern building, we’re stuck looking at that thing and it’s always going to be the gap in the teeth.”

“In terms of creating a humane and habitable cityscape; a place which gives people comfort; a place in which people can feel they belong, that classicism offers a way to make people more connected to the place in which they live,” Daum says. “If you throw out tradition, you basically leave people uneasy, uncertain, anxiety-ridden—not really sure how they’re supposed to behave or what they’re supposed to do.”

The importance of vibrant places—and the technique in urbanism known as “placemaking”—is one of Boys Smith’s biggest concerns, as well.

“A lot of the high density development in London doesn’t work,” Boys Smith says. “It’s too ambitious of density, [there’s] not nearly enough of the human and sympathy in the architecture.”

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Yet perhaps more useful than arguing about architectural style or the economics of development is simply contrasting Boston neighborhoods like the North End and Seaport District. In the North End, typical buildings are only about 20 to 25 feet wide, so facades change frequently. The buildings change height, the patterns built of bricks change, and the level of detailing changes. The pattern is so established that even the occasional breaks in it—the buildings that are longer and less activated, the few parks or even the surface parking lots—end up being welcome contributors to variety. By contrast, the Seaport has no pattern to it. Every building site is an island unto itself. Although the stores within them change, the glass facades are unbroken except for roadways and strips of green space that exist purely to separate one building from another.

These considerations also help explain some of the problems New Urbanist developments experience. Just north of Boston, a 2012 Somerville development known as Assembly Row is a mixed-use assemblage of offices, apartments, and retail that included a new rapid-transit station. Aesthetically, the buildings are decent, and on nice days there can be quite a bit of activity on the main street. Unlike the North End, however, the neighborhood’s vitality drops off as soon as one turns a corner. The likely reason? The development is a kind of latter-day Potemkin village: some happy facades have been designed to disguise all the parking garages, with all the blank, boring architecture those structures have.

Assembly Row, Somerville (YouTube)

It’s an example of what Michael Huston, writing for the Congress for the New Urbanism’s Public Square, called it the “McMain Street”: “Like the McMansion that attempts to mimic the complex roof massing of an entire French village in a single building, the McMain Street attempts to mimic the fine-grained, vertically proportioned facades of the traditional American Main Street—all in a single building. And, more often than not, like the McMansion, the end result appears contrived and inauthentic.”

“We need to be respectful of what’s around us and the history around us when we design new and when we renovate,” Andreozzi said.

“I think you can do traditionally-based work with a certain kind of authenticity that is not making it a stage set,” Daum said. “It is being respectful to local traditions, to the local vernacular; it’s understanding the language of classicism and applying it in a rational way.”

There are successes out there, though. In Britain, traditional architecture and urbanism have a very influential patron in the person of Charles, the Prince of Wales. In 1987 he told a group of London planners, “You have to give this much to the Luftwaffe. When it knocked down our buildings, it didn’t replace them with anything more offensive than rubble. We did that.”

At the time, Prince Charles was putting his money where his mouth was, working with the English town of Dorchester to develop an extension called Poundbury. New Urbanist architect Leon Krier was hired to do a master plan, and construction began in 1993.

“For years derided as a feudal Disneyland…this supposed ghost town feels increasingly like a real place,” wrote The Guardian’s architecture critic, Oliver Wainwright. “Strip away the fancy dress and you find a plan that far exceeds the sophistication achieved by any modern housebuilder.”

According to Wainwright, Poundbury has “genuine mixed use.” Not only are there the usual high-end retail stores and professional offices that tend to be what’s meant by mixed use, but there is also industry, including an aircraft component factory.

“Even though [Wainwright] didn’t like it, he was forced to concede it’s worked,” says Boys Smith.

He adds that it would have been more successful with a clearer High Street (the British equivalent of a Main Street) and that Nansledan, a similar, though larger, project near Newquay in Cornwall, was being built with lessons learned from Poundbury. Greater attention is being paid to the local vernacular architecture and as many local materials are being used as possible.

Poundbury (Wikimedia Commons)

And yet one must still wonder about the role of time in allowing people to get used to architecture. Victor Hugo hated the broad, straight avenues Baron Haussmann built in 19th-century Paris, now regarded as one of the most beautiful cities in the world. Guy de Maupassant led a large group of artists and writers in decrying the Eiffel Tower in terms recognizable to contemporary architectural debates. The book The Invention of Brownstone Brooklyn is replete with contemporary accounts of how ugly everyone thought the brownstones were. In Boston, The North End was once regarded as a slum incubating criminality and disease.

Still, one can look past taste and popularity to the principles underlying architecture and design, which buildings rely on. Daum compares the elements of traditional architecture to a language: “If I understand the language and the grammar of classical architecture well enough, I can write poetry in it,” Daum says.

As no less than poet T.S. Eliot explained in a 1919 essay on “Tradition and the Individual Talent,” these related lessons of architecture and urbanism are just as relevant a century later: “No poet, no artist of any art, has his complete meaning alone. His significance, his appreciation is the appreciation of his relation to the dead poets and artists. You cannot value him alone; you must set him, for contrast and for comparison, among the dead.”

The architect, Daum, ultimately sees this common grammar as central to what makes good urban design work throughout the ages: “If all these different styles are essentially speaking the same language, they are able to relate to one another . . . We’ve lost that common language.”

Matthew Robare is a freelance journalist based in Boston. This New Urbanism series is supported by the Richard H. Driehaus Foundation.