When I was still new to Tokyo, I had only encountered Daikanyama by name—described in passing as an oshare neighbourhood, meaning “stylish” or “fashionable.” That reputation, cultivated over decades, still endures. I wasn’t sure what I expected from such a place, but the streetscape took me by surprise the first time I visited.
Whichever of the station’s four exits you choose, complexity meets you immediately. Buildings of varied styles conform to irregular plots, creating a kaleidoscopic arrangement of shops and homes. Stairwells spiral in Escher-like confusion; walkways crisscross a serpentine mesh of lanes and roads. Beneath it all, an undulating topography subtly asserts itself through the urban fabric. For all its reputation for refinement, Daikanyama might be Tokyo at its most jumbled.
The area wasn’t an immediate favourite of mine, but with repeated visits over the years, I’ve grown used to its idiosyncrasies and developed an appreciation for its unexpected vantage points. Now, trips to Tokyo usually include an afternoon there. My curiosity turned toward the sequence of events that shaped it—there is, as it turns out, a layered architectural history behind the place.
The Shape of Daikanyama
Emerging from the station’s Central Exit gives a reasonably accurate first impression of the area. The station itself is embedded in the base of a commercial block, clad in ageing tile and concrete. It feels more like a service entrance than a gateway—an unceremonious threshold for such a celebrated neighbourhood. To the north, a glass-fronted trapezoid housing second-hand clothing shops clings to a steep slope, while a weathered wooden residence beside it continues to resist redevelopment. Directly ahead stands the stark side elevation of the Tokyu Apartment Annex, a residential building completed in 1959. Just beyond, the first of many cafés and boutiques appear.
Little in the present-day streetscape suggests that, in the Edo Period (1603–1868), Daikanyama formed part of the city’s wooded fringe. Though technically within the official boundaries, it lay beyond the reach of direct administration. The locale was shaped more by woodcutters, irrigation channels, and the occasional samurai residence than by the hand of shogunal governance. It was a quiet neighbourhood in the original sense of the term.
Daikanyama sits on the eastern edge of the Musashino Plateau, a wide expanse of volcanic loam extending west from the Imperial Palace toward the Tama region. Tokyo’s central districts such as Marunouchi, Nihonbashi, and Ginza rest on a low-lying alluvial plain shaped by the Sumida and Arakawa rivers. In contrast, Daikanyama marks a point of geological transition, where the plateau gives way to a landscape of gentle ridges and shallow ravines.
Daikanyama’s characteristic undulation stems from its position at this topographical edge. Streets and roads rise and fall unpredictably—a landscape shaped by centuries of erosion through the soft volcanic soil. These gentle variations in elevation fracture the urban layout and produce a streetscape that feels porous, frequently broken by stairways and unforeseen sightlines.
The neighbourhood of Daikanyama-chō (代官山町) forms a long, narrow strip running from the station at its southern end to the point where the Saikyō Line tracks intersect with Hachiman-dōri to the north. It’s compact enough to avoid subdivision into chōme blocks; the entire length can be walked in about ten minutes. The name combines daikan (代官), meaning “magistrate” in the Edo period, and yama (山), meaning “mountain.” No clear historical record explains the naming, but it implies a distinctive topography and a past association with authority.
For most Tokyoites, the name Daikanyama evokes a broader area than Daikanyama-chō alone. It includes Uguisudani-chō and Sarugaku-chō to the west, as well as parts of Ebisu-nishi to the east. More broadly, the name refers to the entire zone between the Shibuya and Meguro rivers, with Hachiman-dōri and Kyū-Yamate-dōri forming an off-centre axis. This extended, unofficial usage suggests that neighbourhood lines are shaped as much by sentiment as by administrative boundaries. A walking map is available in the members’ area, showing these divisions and offering a route to follow.
A Station by Circumstance
I like to begin the walk from the Central Exit, coasting north down the slope and onto Esperanza-dōri—“Hope Street” rendered in a blend of Spanish and Japanese. At the junction, a time-worn wooden house holds its ground beneath a footbridge that launches from the station toward the Daikanyama Address complex. We’ll return to the history of that development later. For now, we follow Esperanza-dōri northeast as it hugs the Tokyu Toyoko Line tracks.
We pass under the Daikanyamadai 2-Ridō bridge, another structure designed to funnel pedestrians straight from the station into Daikanyama Address. It links into a web of narrow staircases and elevated walkways, intricate and overbuilt. If you saw my Daikanyama reel on Instagram this week, the opening shot was filmed from this bridge: Toyoko Line carriages gliding into a built up cityscape, with a golf range suspended above the scene.
The name Toyoko is a portmanteau: To from Tokyo and Yoko from Yokohama, reflecting the line’s two endpoints. It was never meant to pass through Daikanyama, which partly explains the provisional quality it brings to the streetscape. It feels more like an installation than a fully integrated feature. Daikanyama Station emerged through a confluence of timing, influence, and real estate speculation—less a product of transit planning than of opportunism.
Keita Gotō, the Tokyu Corporation’s former president and a prominent industrialist, maintained ties with Denentoshi Co., a suburban land developer, during the 1920s and 1930s. Together, they aimed to adapt the “garden city” principles of the United Kingdom to Tokyo’s outer districts—a tale for another newsletter. In extending the Toyoko Line to reach these planned communities, engineers initially intended to bypass Daikanyama altogether.
Complications emerged, though. The proposed route clashed with existing developments, military holdings, and sacred grounds near Meiji Jingū. A reroute became unavoidable. Through a web of political and personal connections—particularly Gotō’s relationship with the influential Asakura family, whose role we’ll revisit later, Daikanyama was secured as the site of the alternate route. It was hardly a textbook fit for the garden city model. Yet in 1927, Daikanyama Station opened, permanently altering the trajectory of the neighbourhood.
From Dōjunkai to Address
As we follow Esperanza-dōri, the density begins to thin out, giving way to the quieter scale of a low-rise neighbourhood. At this point, Daikanyama Address “The Tower” rises abruptly to our left. This is the 36-storey residential building of the Daikanyama Address complex. Being the only skyscraper in Daikanyama makes it unavoidably prominent, yet the design remains plain and non-assertive. Functionally, it offers a convenient, modern residence, but visually, it keeps its voice down as much as a solitary skyscraper can.
The land now occupied by Daikanyama Address once supported a very different kind of residential life. In the aftermath of the 1923 Great Kantō Earthquake, substantial public funds were directed toward reconstruction housing. As part of these efforts, the Ministry of Home Affairs founded the Dōjunkai Foundation, a semi-governmental body tasked with building quasi-public housing across the Tokyo–Yokohama region. The Daikanyama Dōjunkai complex once stood on this site, the second largest of all Dōjunkai developments.
Dōjunkai apartments were marked by a bold strain of modernism. They were fireproof and functional, and carried a sense of weight uncommon in residential buildings of their time. The Daikanyama complex followed this pattern: reinforced concrete paired with restrained ornament. Unlike the postwar danchi housing model, which often involved flattening terrain to accommodate rigid layouts, the Daikanyama site was developed in response to the land's natural contours. Its design prioritised visual rhythm and spatial variation. Arches, gates, stairways, and curved lanes; terraced green spaces and small landscaped plazas.
The complex, rooted in a vision of urban life shaped by civic ideals, evolved over seventy years. It survived the Second World War and the events of Japan’s post-war history, first as a symbol of reconstruction, then as a coveted address for professionals. Later, it became a retreat for designers and intellectuals, and eventually, a subject of architectural nostalgia. By the 1990s, it was a structural liability, outdated and vulnerable to earthquakes. Demolition of the Daikanyama Dōjunkai Apartments began in 1996.
Instead of selling the land or allowing a wholly commercial redevelopment, residents of the ageing apartments formed an association and collaborated with the Tokyo Metropolitan Government. This gave them some measure of influence over how their homes and neighbourhood would take shape. The result was the creation of Daikanyama Address. At first glance, it may not appear so, but this was one of Japan’s earliest experiments in resident-led urban renewal.
On one hand, Daikanyama Address prioritised continuity with its surroundings, aligning with the area’s natural terrain and continuing to preserve its genius loci—the underlying spirit of place. On the other, it carried forward certain less favourable traits of the original Dōjunkai complex. Rather than joining existing chōkai neighbourhood associations, Dōjunkai residents had maintained their own independent body. As a result, the complex was always somewhat detached from the broader social cohesion of Daikanyama.
From my outsider’s standpoint, Address exudes a similar air. Its extensive presence in the neighbourhood is accessible only through a commercial corridor—a form of privatised permeability where pedestrian passage is predicated on consumption. This controlled access reflects a broader mood that infuses Daikanyama.
Modern Detours
There are a couple of brief detour options at the crossroads near the tower. To the east is Chacott Daikanyama. Personally, I’m more a fan of the 1959 Tokyu Apartment Annex aesthetic, but this building, with its composition of small stacked boxes, has a certain appeal at blue hour. It combines contemporary minimalism with influences from High-Tech architecture and Neo-Modernism.
Still, it feels more like a showroom than a contributing part of the street. It’s something to look at, not something to live around. I came across a review of Chacott that framed it as a textbook case of architecture as marketing. It wasn’t clear whether that was meant as praise or critique, but it is a dynamic that recurs throughout the neighbourhood.
Heading west, you climb into the shifting terrain of Ebisu Nishi, where independent businesses and private homes adapt to the irregular land. It’s a rewarding place to see how a Tokyo neighbourhood takes shape in response to difficult topography. But just before that, a narrow side path to the left leads to Log Road, a regreened tunnel running parallel to Esperanza-dōri.
Log Road is lined with trees and angular wooden buildings, home to businesses like a craft beer brewery and a sneaker shop—an inventory that reflects the priorities of a younger, modern Tokyo. It doesn’t carry the layered atmosphere of a narrow yokochō alleyway, but it succeeds as a hidden shortcut. The sudden shift into greenery offers a kind of relief, one you may not have realised you needed after the surrounding press of concrete. The path ends at a viewing deck, where a metal staircase takes you up to survey the neighbourhood from above while Esperanza-dōri babbles by below.
Castle Street
Tempting as Log Road is, I prefer to remain on Esperanza-dōri, which here begins to resemble a casual, contemporary version of the traditional shōtengai shopping street. If travel guides have praised Daikanyama for its boutiques and cafés, this is where to sample that version of the neighbourhood. A steep staircase branches off the main path, lifting you into a compact residential pocket before returning you to street level—now facing Castle Mansion Daikanyama. Chacott has its appeal, but this is the architecture I came for.
Castle Mansion Daikanyama was built in 1985. Its age is discernible in the kitschy faux-European façade, complete with balustrades, Ionic columns, and pastel stucco, paired with the density and shopfront pragmatism of a typical Tokyo walk-up. It is a collision of suburban Versailles pastiche and squeezed urban function, oddly delightful and entirely out of place on the streetscape.
Locals refer to Esperanza-dōri as Castle Street in honour of this surreal beauty. If I were to choose a building to house a Tokyothēque office, it would make the shortlist. Across the street is Café Façon Roaster Atelier, the best coffee option we've passed so far. A single seat out front offers just enough room to sip an espresso, take in the castle, and watch the neighbourhood drift past.
Industry and Agriculture
Esperanza-dōri continues to unfurl. It is lined with a chaotic mix of buildings as if someone had detonated an architectural seed bomb in the middle of the neighbourhood. Eventually, a discreet side street, marked by a red vending machine, threads upward through a tight residential network before spilling onto Hachiman-dōri, the main road. We cross at once and continue northwest, reaching a steep, narrow slope marked with graffiti. At the top, a small plaque subtly delivers a bit of history:
Tengu-zaka (Tengu Slope) Sarugaku-chō, Block 5
This slope is known as Tengu-zaka, named after Iwaya Matsudaira, who published under the pen name Tengu. Born in Kagoshima in 1849 and living until 1920, he moved to Tokyo in 1877 and soon established the Iwaya Tengu Shōkai in Ginza, a company specialising in rolled cigarettes. His products bore names like Golden Tengu and Silver Tengu and were advertised with flamboyant slogans, including: “Tobacco tax revenue: 3 million yen! The nation's best ally!”—a line that distilled the brash energy of the Meiji period.
He was known for his pioneering approach, notably the introduction of home-based labour into tobacco production. After the Tobacco Monopoly Law was enacted in 1885, he relocated his operations to this area, acquiring approximately 43,000 square metres of land. Convinced that greater meat consumption would strengthen the physical constitution of the Japanese people, he launched a large-scale pig farming enterprise—framed as a contribution to the national good.
In his later years, Iwaya Tengu lived here—thus, the slope came to bear his name.
Tengu-zaka provides a window into Daikanyama’s in-between phase. The Meiji Era (1869–1912) saw the area take on an industrial character, with ventures such as Matsudaira’s pig farming. This period bridged its pastoral Edo-era origins and its later development as a residential and then commercial district. Local records suggest Matsudaira later sold portions of his expansive estate, setting in motion the gradual fragmentation of land ownership that shaped the neighbourhood’s later form.
Daikanyama also supported green tea cultivation, with a local variety known as Shibuya-cha grown on these hills. Over time, it lost prominence as Shizuoka-cha became Japan’s dominant tea. Cotton mills, too, operated here, driven by large waterwheels—many powered by the area’s natural slopes. These gradients, once harnessed for industry, still influence the neighbourhood’s circulation. In places, former canal beds were repurposed as roads, their shapes still traceable in certain paths that carry the feel of ankyō streets¹.
The Backstreets of Sarugaku-chō
From the base of Tengu-zaka, a quiet, southwestward walk offers a welcome pause. The street traces the exact boundary between Uguisudani-chō and Sarugaku-chō—a stretch of everyday Tokyo defined by the walled grounds of Jōsenji Temple and a layering of apartment buildings. The mood remains subdued, almost deliberately so.
Soon, a few bohemian cafés begin to appear—an early sign that we’re re-entering more active territory. Watch for a narrow lane on the left, marked by a row of blue and white vending machines. It leads into a winding sequence of turns, which I’ve tried to highlight clearly on the walking map. As you proceed, a shift takes place. The building types stay the same, but their function changes: homes become shops, and private space becomes public-facing. It’s a residential neighbourhood, hollowed and reinhabited by small-scale commerce.
In the 1980s and 1990s, Daikanyama emerged as a soft-focus backdrop for Tokyo’s aspirational imagination. Its appeal hinged on comparison with nearby Shibuya and Harajuku. Where those districts grew louder and more performative, Daikanyama remained restrained: calmer, more curated, and quietly oshare. Repurposed homes welcomed a new generation of boutique retailers and design studios, many homegrown in the neighbourhood itself.
In the fashion and lifestyle magazines of the time, Daikanyama was cast less as a place to shop but as a way of living. Over time, the residential enclave became a mood board shaped by media coverage and aspirational branding. Despite being zoned residential, Daikanyama is no longer seen that way—its identity transformed by the commercial growth of the post-1980s period.
T-Site Estate
We pass Maison Kitsuné’s Daikanyama store, which was constructed with visible pillars and beams that evoke the structure of a traditional Japanese house. A branded noren² hangs at the entrance—part nod to custom, part brand signature. The store marks the rising interest among foreign brands in securing a foothold here. Maison Kitsuné sets a precedent with its thoughtful storefront design, a sensitivity I hope others will take note of.
Just past Kitsuné, a discreet black sign affixed to a stone wall signals the rear entrance to Daikanyama T-Site. I wrote at some length about this complex and the Tsutaya Bookstore at its centre in a previous newsletter on Tokyo’s bookshops³, which I’ll link at the end. What follows is a short excerpt:
Daikanyama T-Site's placemaking was executed precisely, sparing no expense in gathering the right talent. The striking white façade, a lattice-like design incorporating the letter 'T,' was designed by Klein Dytham Architecture, selected from 80 competing firms. Kenya Hara developed the communication design, while Tomoko Ikegai led the creative direction. At the centre of it all is a gleaming new branch of Tsutaya Books, which earned a spot as the sole Japanese entry in Flavorpill's 20 Most Beautiful Bookstores in the World.
The earlier newsletter covers T-Site in detail, so I’ll take a different angle here. The land now occupied by T-Site was once the residence of Tokugawa Kuniyuki, the 13th head of the Mito branch of the Tokugawa clan. This detail places Daikanyama within a long lineage of elite retreat. During the Edo period, its position on the Musashino Plateau made it suitable for samurai estates—removed from the clamour of the city but close enough to maintain proximity to power.
This legacy extended through Meiji and into the Taishō Era (1912–1926) as former samurai estates gave way to residences for industrialists, politicians, and financiers. Nearby, the Kamejima Residence later housed Ataru Kobayashi, president of the Japan Development Bank. The Murai Residence, once a symbol of zaibatsu affluence, was demolished in 2019 following its repurposing as the La Fuente Daikanyama complex. These sites chart a continuity of privilege: from samurai authority to Meiji-era retreat to a present shaped by commercial redevelopment.
Artistic Presence
From the T-Site exit, we cross Kyū Yamate-dōri into the Aobadai district and detour down a steep slope. On the corner stands a building clad in a Daikanyama-esque faux-ivory façade. The path carries us downhill to the former residence of Misora Hibari, known affectionately as the Hibari Goten, or “Hibari Palace.”
Misora Hibari is widely regarded as Japan’s most celebrated postwar singer, her career extending across enka, kayōkyoku, jazz, and film. She earned the lasting title of “Queen of Shōwa.” Her home, preserved by her children and partially open to the public, offers a rare look into her personal life. Inside, little has changed: her purple piano sits untouched, and outside, her Cadillac remains parked where she last left it. The house feels suspended in time, a window into the life of a cultural icon.
Misora was among a wave of prominent artists and entertainers who settled in Daikanyama during the 1970s and 1980s when the area stood at the cultural edge of Tokyo, prized for its affluence and quiet remove. She was joined by figures like actor Kiyoshi Atsumi, singer Akira Fuse, and designer Kansai Yamamoto, each adding to the neighbourhood’s growing identity as a creative quarter in the capital.
Hillside Terrace
Looping back to Kyū Yamate-dōri and heading southeast, we arrive in the heartland of Hillside Terrace. This development, arguably more than Dōjunkai or Daikanyama Address, defined the pattern of modern Daikanyama. Spanning just over 200 metres, the project consists of more than ten buildings, each positioned within a compact and easily walkable area.
As promised earlier, we return to the story of the Asakura family. This prominent lineage evolved from agrarian origins into influential roles in commerce, politics, and urban development. Having settled in Daikanyama during the Edo period, the Asakuras acquired substantial landholdings. Many of their properties were lost in the air raids of 1945, and from the 1960s, the family began to reorient their estate.
The clearest expression of this came in the development of Hillside Terrace, a collaboration with the late Pritzker Prize–winning architect Fumihiko Maki. The first buildings were completed in 1969, launching a seven-phase construction process that extended through to 1992. Rather than opting for conventional apartment blocks, the Asakura family asked Maki to propose something more forward-looking. While retail had not initially been part of the plan, Maki suggested integrating shops into the ground floor of each building, establishing the mixed-use model.
When the project began, Daikanyama had no boutiques and no trending restaurants. Each tenant was hand-selected to align with the vision for the development. The community took shape through personal connections, and many early tenants were friends or acquaintances. Notable fixtures included Bricks, a French pâtisserie favoured by writers and musicians; Aota Beauty Salon, known to have served Hibari Misora and Kirin Kiki; and Toms Sandwiches, a kissaten-like shop where actors and former prime ministers could eat in peace. The basement levels became studios for emerging architects and designers.
This is a case study in how architecture can shape the character of a town. A single client family, working with a visionary architect, created a distinctive sense of place through deliberate planning and long-term reinvestment. The selection of tenants, the integration of homes, shops, and offices, and the sensitivity to Daikanyama’s uneven terrain formed a durable and compelling blueprint. Indeed, the shop-lined back streets of Sarugaku-chō emerged as a spillover effect. Even the design of T-Site, completed in 2011, reads as a quiet extension of the Hillside Terrace philosophy.
At the far end of Kyū Yamate-dōri, a visit to the Kyū Asakura Residence, built in 1919, offers a look into how the Asakura family lived during the Taishō and early Shōwa periods: surrounded by landscaped greenery yet anchored to the commercial and political centre of Tokyo. The house, now designated an Important Cultural Property, is an unusually well-preserved example of Taishō Era domestic architecture. It blends traditional Japanese design with early modern influences and remains the only intact estate of its kind in Daikanyama.
The Path to Forestgate
We return to the junction where Kyū-Yamate-dōri ends and Hachiman-dōri begins. Having circled around it for much of the walk, we now head directly down Hachiman-dōri. Not far along, we arrive opposite Forestgate, a striking mixed-use complex designed by Kengo Kuma and completed in October 2023. Forestgate is a conclusion that stirs mixed feelings but a fitting one.
As the first major complex built in Daikanyama since T-Site, it brings us into the 21st-century phase of the neighbourhood’s development. Between 1990 and 1999, daily passenger numbers at Daikanyama Station more than doubled, but the growth peaked in 2000 with the opening of Daikanyama Address and has gradually declined since. The flattening suggests a shift in what ‘Daikanyama’ signifies—no longer an emerging district, but a maturing brand in slow transition.
Daikanyama Address was a structural success, but it revealed a gap between the original vision of community-oriented urbanism and the preferences of its affluent, often transient residents, who were more drawn to convenience, prestige, and insulation than to neighbourhood engagement. Taken as a symbol, it reflects both the ambitions of urban progress and the challenge of retaining communal memory amid ongoing transformation.
In Hillside Terrace and Sarugaku-chō, many of the iconic brands that defined the 1980s and 1990s eventually shuttered or faded—frequently absorbed by large apparel conglomerates. The local character in these portions began to erode as chain stores and outside brands moved in. After 2000, few new Daikanyama-grown brands emerged. Key properties were acquired by real estate investment trusts and institutional funds, where financial return took precedence over neighbourhood identity.
It is a feeling that comes to the surface when standing before Forestgate. Despite its gestures toward ecological design, the building’s true posture toward the neighbourhood is harder to romanticise. From street level, it presents a carefully composed façade, softened by timber fins and greenery. Yet above this podium sits a stack of exuberantly priced luxury apartments—homes that, despite the sustainable rhetoric, speak more to financial positioning than to local integration.
Now, it’s only a short walk back to the station—a brief return route that offers one final glimpse of Daikanyama’s enduring reputation as an oshare neighbourhood. Through a more critical lens, that image feels increasingly inherited, propped up by media repetition and speculative value rather than present-day vitality. It’s still called fashionable, but often out of habit. The cultural edge has largely moved on.
On a more generous note, I’ve never been especially concerned with whether a neighbourhood is fashionable. Beyond the commercial churn, Daikanyama’s irregular contours—its peaks and dips—preserve a form of human-scale urbanism shaped over time. Memory anchors itself in unconventional landmarks, and absurd spatial beauty reveals itself from those unexpected sightlines.
If the surface sheen of a neighbourhood outpaces its soul, then perhaps the task is to look closer. In doing so, we see that Daikanyama’s genius loci still flickers.
Until we meet on Castle Street,
AJ
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Links
¹ Ankyo Redemption
² The Noren Code
³ A Library in the Woods