Take a guided tour of Melbourne’s newly-groovy Gertude Street, with Holiday Goddess Donna Wheeler, author of Lonely Planet’s  Melbourne Encounter and Milan Encounter guides.

The Albanian social club set has moved on, but Melbourne’s most freshly fashionable neighbourhood is not entirely without remnants of its past. Spliced among the peddlers of deconstructed Belgian frocks, rare vinyl 12inches and mandarin-scented hand cream, stalwarts remain: a second-hand fridge shop, the Aboriginal gym that trained boxing great Lionel Rose, habit-clad Sisters of Charity, residents of rooming houses and public housing tower blocks.

As recently as the early ‘90s this was a street that didn’t lend itself to casual evening strolls; there were pubs where it was rumoured you could ‘get jobs done’, and we’re not talking lawn mowing or paving. The stark contrasts of affluence (even in stealth-wealth guise) and disadvantage can still unsettle, but there’s a mitigating energy and a relaxing, welcoming, community vibe.

Closest to the Exhibition Buildings one side of the road is still dominated by St Vincent’s hospital services. The other side has handmade pioneers Little Salon (no.71) and Cottage Industry (no.67). There’s also the cute café Radio (no.79) and on the corner of Brunswick Street, the former Rob Roy Hotel, made over as the Newtown Worker’s Club by city laneway pioneer himself, Jerome (RIP St. Jerome’s). Serious dining can be done behind the unprepossessing glazing at Cutler and Co. – Andrew McConnell’s cooking is arguably the city’s most thoughtful (and deliciously so), while Pascale Gomes-McNabb’s moody interior  similarly mixes smarts, glamour and comfort (no.55-57). If you’re not up for a three-course blowout, it’s an equally lovely spot for oysters and Arneis at the bar.

Across Brunswick St, there’s excellent vintage clothing and accessories at Curve (no.158;), Circa (no.102) and Moustache (no.124), as well as an always intriguing array of furniture and collectibles at Fitzroy South Antiques (no.90), Three Quarters (no.128) and Max Watt’s Industria (no. 202).

Gertrude St style tends towards the cerebral. L.E.F.T (no.161) stocks international heavyweights: think art-mama darling Yohji Yamamoto and luxuriously girl-does-boy cuts by Anne Valérie Hash.

Working in a similar vein are talented local design duo Ess. Laboratory (no. 114), worth a look for the theatrical window displays never mind the beautifully realised clothes. They’ve recently been joined by fashion forward retailer  Assin (no.126). Further east are  Nom-D (no.203), with their own edgy label as well as other cutting-edge Kiwi designers, and the less highbrow Obüs (no.226), a northside favourite that combines hipster cool and girly charm.

Spacecraft (no.225) has a collection of botanical and architecture-inspired screen-printed homewares, clothing, stools and screens. Their GPO-printed socks are a particularly fitting Melbourne memento.

With delightfully obliging staff, Artisan Books (no.159) stocks a wonderful range of decorative arts monographs, and Books for Cooks (no.233) are prime browsing destinations. Books for Cooks has an amazing collection of both new and second-hand gems, from the latest from big name chefs to lovely arcane gastronomic histories. Title (no.183) stocks covetable CDs and iconic DVD boxsets. Northside Records (no.236) is where DJs shop for classic vinyl from Curtis Mayfield to NY hard salsa to dub and hip hop.

Ladro (no.224a) epitomises Melbourne-casual dining, both in its dreamy signature Lazio pizza, smeared with artichoke and anchovy paste and sweet fior di latte, and in their Mod Italian brio and nightly buzz.

Across the road, Gertrude St Enoteca (no.229) serves up lovingly selected wines by the bottle or the glass, as well as simple, spot-on snacks sourced from Victoria’s top suppliers. It’s not all about vino either; it’s equally pleasing for morning coffee and a slice of their olive oil and marsala cake. Birdman Eating (no.238) does a cut-above big breakfasts, and Añada (no.197) opens in the evening for tapas and tastes of the Muslim Mediterranean matched with Iberian wines.

The once rough-as-guts Gertrude Hotel (no.148) and the Builder’s Arms (no.211) are now firmly in the hands of the young and the hip, but still manage to be comfortable old boozers if a beer beckons. The Builders also does great Middle Eastern inflected bar snacks and proper meals in its hysterically decorated dining room. Aesop (no.242), the luscious local skincare outfit, has an airy shop to refresh the senses before you hit the onslaught of Smith St.

Finally, no Gertrude St stroll would be complete without art. Head to Gertrude St Contemporary Art Spaces (no.200) and Seventh Gallery (no.155) for up-and-coming action. Around the corner at 89 George Street, Lamington Drive specialises in illustration and design, with affordable pieces on sale both at the gallery and online. While you’re in George Street, don’t miss Third Drawer Down at no.93, for limited edition, and often usable (eg tea towels), printed works.