Danielle Demetriou discovers that time is running out for a district of hip shops and smoky pubs in the Japanese capital

Thick smoke and swirling jazz fill the air as a silver-haired man with melancholy eyes sitting at a nearby table removes the pipe from his mouth and looks sharply in my direction. We may be sitting in a tiny, windowless café on a sunny Tuesday afternoon but the message is clear: "You are talking too loudly for me to appreciate the music. Please be quiet."

Only in Shimokitazawa. Or Shimokita. Or Shimo. Or simply the Kitz – depending on your age, who you hang out with and how hip you are. And, for the uninitiated, it is very easy to feel unhip in Shimokitazawa, an atmospheric neighbourhood in west Tokyo only minutes by train from the heart of the Japanese capital.

Shimokitazawa is a haven for the coolest of eccentrics and music lovers, creatives and bohemians. With its network of tiny lanes, underground theatres and vintage stores, its independent spirit could not be further from the shiny skyscrapers and fashion towers synonymous with other parts of the city.

This is the Tokyo equivalent of East Village in New York or Hoxton in London: elderly residents pass by on bicycles, cutting-edge fashion-lovers peruse some of the best vintage stores in the capital, and edgy students squeeze into all-night live music venues.

But there is another reason to visit Shimokitazawa: the area is on the brink of extinction. Controversial city council plans include the extension of a highway through the heart of this much-loved neighbourhood.

Although residents have joined forces to oppose the idea, work is already underway, and as early as 2010, Route 54 is expected to have made its appearance. With the clock ticking, it makes sense to explore the area sooner rather than later.

Stepping out of the station, a tangle of quiet lanes and alleyways runs off the bustling main shopping street. There seems not to be a car in sight. My first stop is the tiny Masako jazz café. Inside, time seems to stand still. The decor is grungy retro chic, there's a wall of manga comics and a booth brimming with records. Solitary old men and hip young couples alike are smoking intensely, staring into space and drinking black coffee. It feels a little as if I've stepped into a Haruki Murakami novel.

I sit at a low table and order drinks and music (every table, it transpires, can make a request for one jazz track only). I have company: my underground guide for the day, Benjamin, a stylish design PR from the US and a long-term Shimokita resident. Sipping a mug of hot lemon water – a house speciality, apparently – he explains: "When I moved to Japan, I wanted to find Tokyo's equivalent of New York's East Village – and the first time I saw this place, I knew I wanted to live here. That was eight years ago. I love the atmosphere."

Café culture is big in Shimokitazawa, and so is shopping. Dozens of vintage stores pepper the streets and lanes. Hola! is a minuscule vintage clothing shop at the top of a wobbly metal staircase. It's filled with "All Charm Things for Girls!", as its sign proclaims. For men, there is the trend-setting Grand Global, a treasure trove of vintage suits, bags and jackets, with many items customised on a sewing machine at the back of the store.

Shimokita is not too cool to embrace kitsch, as we discover at Bubble Bubble, a quirky food outlet that churns out everything in sealed clear plastic cups – including delights such as squid eggs spaghetti in a cream sauce. An acquired taste, even if it is a credit-crunch friendly Y430 (£2.70).

Keen to showcase better cuisine than plastic pasta, Benjamin declares that it's dinner time. Numerous izakaya (Japanese-style pubs) serving good, cheap food line the streets, but we head instead to Katsuryou, a 35-year-old restaurant that is said to serve the best tonkatsu pork cutlets in Tokyo.

Large paper lanterns, colourful ikebana flower displays and rows of blue-and-white china teacups set a homely tone. After slipping off our shoes, we tuck into a hearty pork feast at a low wooden table.

It is later, after wandering the south side's alleyways and waiting at one of the old-fashioned railway level crossings, that the area seems to be at its most seductively atmospheric and charming.

We pause at what appears to be a pink kiosk attached to the front of someone's house. Brimming with an armada of fluffy Disney toys, it resembles the inside of a young girl's bedroom, but is in fact a popular local crêperie. On another quiet lane, there is a neat queue of elderly ladies and young hipsters outside a small yellow kiosk under a red lantern waiting for another culinary treat: the best takoyaki (octopus balls) in town.

As we wander, Benjamin fills me in on another of the area's attractions. Some destinations have avant-garde art galleries; others boast historic architecture. Shimokitazawa, says Benjamin, is also home to Hot Pants Man. A well-known local character, the middle-aged fancy dress aficionado never leaves home without his winning combo of tight Lycra hot pants and a navel-baring tank top.

Sadly, there is no sign of him tonight at his favourite Italian café, so instead we pop into Eat a Peach for a nightcap. Quite possibly one of the tiniest bars in the world, its four customers cheerfully stand up or step outside so we can squeeze into the corner. Testament to its diminutive size is the fact that the bartender has to go upstairs to get our drinks, then shows off his ninja skills by leaping back in through the window without spilling a drop from the glasses he is carrying in each hand. Against a soundtrack of early Seventies soul, the long-haired, black-clad barman continues to leap in and out of the window throughout the evening, bearing round after round of glasses.

Surveying the scene, it's clear that, although time is ticking for Shimokita, it remains home to the city's most colourful cast of characters. For now, at least.

Traveller's Guide

Getting there

Tokyo is served from London Heathrow by Japan Airlines (0845 7747 700; uk.jal.com), ANA (08708 378 811; anaskyweb.com), Virgin (08705 747 747; virgin-atlantic.com) and British Airways (0844 493 0787; ba.com).

To reduce the impact on the environment, you can buy an "offset" through Abta's Reduce my Footprint initiative (020-7637 2444; reducemyfootprint.travel).

Getting around

To get to Shimokitazawa in Tokyo, take the Odakyu line from Shinjuku station or the Keio Inokashira line from Shibuya station (tokyometro.jp/e).

Visiting there

Jazz Coffee Masako, 2-20-2 Kitazawa (00 81 3 3410 7994).

Hola! 2-14-18 2F Kitazawa (00 81 3 3218 2242).

Katsuryou, 2-3-12 Kitazawa (00 81 3 3412 5990).

Grand Global, 2-14-13 Kitazawa (00 81 3 5787 4550).

Eat A Peach, 2-19-18 Kitazawa (00 81 3 3460 1468).

More information: Japan National Tourist Organisation: 020-7398 5678; seejapan.co.uk