Tailor-made sightseeing: East London walking tour

Her eyes may be bigger than her credit card limit, but Sophie Lam just about kept a leash on her purse during a fashion-conscious walking tour through super-hip East London

I was standing face to face with a wild boar, its hirsute face fixed in an enduring snarl. But rather than encountering it in the forests of central Europe, I was standing in the basement of A Child of the Jago, the East End's latest concept boutique. Opened last month by Joe Corre (punk progeny of Vivienne Westwood and Malcolm McLaren), the shop seems to capture the energy and creativity of this off-kilter pocket of London.

The stuffed boar is just one of the many curios collected by Corre and Simon "Barnzley" Armitage, designer of A Child of the Jago's "Terrorist" line of clothing. With a loose theme revolving around Napoleon and Velásquez, the shop is filled with anything from old military attire to luxury cashmere zip-ups and an old prosthetic leg, punched through with lettering spelling out Hells Angels. Vintage clothing doesn't mean granny's old dresses: this is all genuine coachmen's jackets, Pearly King suits and Native American Indian headdresses.

The shop was named after the novel of the same name about the slums that once demarcated this part of town. It was a fitting first port of call on my East End Hip tour.

Run by the suavely named Urban Gentry, it started at Old Street underground station, where Kevin Caruth – the company's founder and my rather desirable companion for the morning – handed over a Moleskine London City Notebook. With the aid of the book – with its maps, travel planner, clothing size conversion chart and reams of pages for notes – and Kevin's insider knowledge, we attempted to create my own personal tour of Shoreditch and Spitalfields, revealing the newest shops and hippest artistic spaces. Once notorious for poverty, dereliction and crime, the area has in the last decade become a hub of creativity and cool. It's a textbook example of urban regeneration, albeit with a slightly renegade approach.

Kevin set up Urban Gentry in late 2006 to fill a gap in the market for tours of the capital that looked beyond Big Ben and the London Eye. There are off-the-shelf tours, covering themes from markets to fashion and architecture, or bespoke outings which can be created according to clients' interests. To date, the most unusual request has been for a tour focusing on mid-century Danish furniture. Using 10 field specialists, rather than all-singing, all-dancing tour guides, Urban Gentry is able to offer the insider's view on anything from men's tailoring to 21st-century architecture. The crux is to help clients feel that they're visitors, not tourists, by opening up the little black books of the specialist guides. Yet they're not geared exclusively towards visitors; they have also become popular with Londoners who want to re-familiarise themselves with parts of this often impenetrable city.

From Old Street we ambled down the arterial Great Eastern Street – pleasingly deserted on a Friday morning – peeling off to stop at Gallery Fumi, a new high-end shop which sells vintage pieces of design furniture in a gallery environment. The centrepiece was a huge tumbling chandelier created from daintily-etched wine glasses. Unlike other "shop tours" I had been on, there is absolutely no obligation to buy anything, which, given the price tags at Fumi, was something of a relief.

After the high-end retail extravaganza of A Child of the Jago and Fumi, we dipped into the Association of Photographers gallery, where revolving exhibitions feature both professional and amateur photography. An exhibition of black-and-white images of street life in London, Paris and Havana was on display, depicting evocative imagery of kids hanging out on street corners and an old man sipping tea in a Camden café.

Across the road, in what looked like a cross between a church, junk yard and film set, was Westland. The architectural salvage emporium specialises mostly in historic fireplaces, but as we wandered around the former St Michael's Church, we came across Renaissance pieces, Victorian ornamentation, even a vast cast-iron clock tower from the Royal Ascot racecourse. Over the last two years, Kevin has built up a relationship with the retailers and gallery owners he visits, so you feel completely at ease window shopping and browsing.

Next up was Start, a boutique that I could have been tempted to dip into my purse for, despite the price tags. Tucked away down Rivington Street in three idiosyncratically restored Victorian buildings, they specialise in style-savvy men's and women's wear. Opened in 2002 by former Fall guitarist Brix Smith-Start and her husband Philip, it's the sort of place you want to linger in for hours, with its hand-drawn wallpaper, giant mirrorballs and labels running the gamut from Acne Jeans to Zoe's Tees. One dress I just couldn't stop picking up.

Purse still fastened, I exited and continued down Rivington Street, past the imposing new Rivington Place gallery – the first new build public gallery to open since the Hayward in 1968. The brooding, black building with its thorny roof and Rubik's Cube-construction sat comfortably amongst the Victorian brick buildings, and was a perfect preamble to a visit to its neighbour Cargo, a bar and music venue where some of Banksy's early work can be found in its garden (now under sheets of protective plastic). At the back of the garden terrace, housed under the railway arches was the Black Rat Press, a gallery space for street art that has exhibited the likes of Blek Le Rat, Faile and Slinkachu, who photographs minute plastic people in city settings. The gallery was preparing for a Big Issue charity show, so we got a preview of donated works from Blek Le Rat, Julian Opie and more.

Rather than take the direct route to Brick Lane via Shoreditch High Street, Kevin directed me down a side street. Redchurch Street looked on first inspection fairly unassuming – other than the major construction work on the site of the new Conran hotel and restaurant project, The Boundary, due to open later this year. But beyond the scaffolding were yet more obscure boutiques, one selling spray-painted Louis XV-style furniture. Further on, we rang the doorbell of what looked like a boarded-up house, only to be let into Museum 52. The minuscule contemporary art gallery was swathed in a headache-inducing installation of black and white lines, created with black electrical tape.

By the time we reached Brick Lane, Kevin had assessed my tastes and was directing me towards shops that I knew I'd be returning to, armed with a credit card. My favourite find was just off Brick Lane – Cheshire Street, which has been touched up with easy-on-the-eye Farrow & Ball hued-shop fronts. It has a period drama quality, but rather than old-fashioned tailors and butchers, the shops are full of designer rustic homeware (Labour and Wait), stylish womenswear (Dragana Perisic), eye-catching homeware (Ella Doran) and even an old shoe shop dedicated entirely to plimsolls (The Devil Wears Prada but the People Wear Plimsolls).

We ended the tour by heading over to the cosmetically enhanced Spitalfields, once the heart of the French Huguenot immigrant community who set up their silk weaving and textiles industry here in the late 17th century. The legacy has endured: keep your eyes peeled for Fashion Street, just off Brick Lane.

"It feels like Covent Garden did maybe 15 years ago," Kevin said, as we passed the shiny new glass additions to the 19th-century fruit and vegetable market. We made our way to Liverpool Street station via Brushfield Street, where old wooden Georgian shop fronts have been restored, providing equilibrium to the surrounding soaring glass offices. At the station, Kevin went back to his office, as I should have done. But not before I retraced my tracks and had another look at that dress...

Urban Gentry (020-8149 6253; www.urbangentry.com) offers the half-day private East End Hip walking tour for £149 for a group of up to four.

For more information visit www.enjoyengland.com