While the Prahran and South Yarra chunks of Chapel Street thronged with designer attractions, the Windsor end used to be a scrabbly terrain of op shops and not a whole lot more. Now it (and the rest of the suburb) is an effervescent, energetic dining enclave with an emphasis on fun and affordability.

Sure, the chains are there – Lord of the Fries, Ben and Jerry's, Mad Mex, Grill'd, the obligatory frozen yoghurt joints – but Windsor has developed a natty gastronomic style of its own, with Asian street food and great bar dining at its forefront, and new restaurants blooming almost weekly. Windsor can be a tale of two cities - laidback and quiet during the day, exploding at night with a teeming bar scene, especially on weekends – so here's a rundown to help you find your patch.

Breakfast – with killer coffee

Fancy starting your day with beetroot and sweet potato fritters and coffee from Monk Bodhi Dharma? Then head to Two Lost Boys, tucked down next to Windsor Station. Plenty, the latest cafe from Jason Chan, the brains behind Balaclava's Batch, serves Coffee Supreme and supreme breakfasts. School of 7 Bells, with a rich, Spiegeltent-like interior, pulls excellent Artful Dodger coffee and serves brekkie tacos and red velvet pancakes, while its related cafe, Brick Lane, around on High Street, takes a tapas approach to breakfast. Windsor Deli goes super cosy with house-baked croissants and Clement Coffee, Sticky Beak do a wild coconut tapioca amid artful surrounds, and Dukes, well, for those who believe coffee is breakfast, this roasters is the bee's knees of caffeine.

Two Lost Boys, 20/2 Maddock St, 9939 9313
Plenty, 78 Chapel St, 9529 7496
School of 7 Bells, 33-35 Chapel St, 9521 5535
Brick Lane, 89 High St, 9095 6312
Windsor Deli, 33 Hornby St, 9529 3001
Sticky Beak, 40 Green St, 9533 7380
Dukes, 169 Chapel St, 9521 4884

Time for lunch?

For a super cheap eat, Lucky Coq, the southside cousin of Fitzroy's Bimbo Deluxe, offers good $4 pizzas. Tyranny of Distance, a quirky indoor/outdoor dining space in an old garage offers “stacks” of house-cured salmon on potato rostis, The Wolf and I does a cosy Sunday roast among other pub faves, and Mileto's Cafe and Deli offers lighter, Italian-leaning salads in a cute, cottagey space. Morris Jones & Co kicks it up a notch with a finessed contemporary menu that includes ridiculously good pork rillettes and kingfish tartare.

Lucky Coq, 179 Chapel St (corner High St), 9525 1288
Tyranny of Distance, 147 Union St, 9525 1005
The Wolf and I, 152 Chapel St, 9510 1819
Mileto's Cafe and Deli, 132 Chapel St, 9510 2241
Morris Jones & Co, 163 Chapel St, 9533 2055

Asian street eats

Windsor has had an explosion of alliterative Vietnamese restaurants, from the kitsch yet luxe Saigon Sally (tea-smoked duck, Saigon chilli crabs) to knockabout little sister Hanoi Hannah (budget-friendly pho, banh mi and rice paper rolls with an Express Lane takeaway shopfront two doors down). Charlie Dumpling puts an artful spin on the humble 'pling in a dumpling-sized little eatery, while Suzy Wong is a bigger, roomier and more upscale operation with innovative dishes like lily bud dumplings and pho-spiced flank.

Saigon Sally, 2 Duke St, 9939 5181
Hanoi Hannah, 180 High St, 9939 5181
Charlie Dumpling, 184 High St, 9510 4213
Suzy Wong, 12 Chapel St, 9510 1875

Burgers

Those on board the burger train will want to get off at Windsor station and start at Parlour Diner or head further down for the customised devils at Babu – choose your burger size, how you like it cooked, and the extras you want on it, like maple bacon, basil cream cheese, you name it. Alternatively, you can grab a tried, trusted and worshipped Huxtaburger at its spacious, red-and-chrome southside outpost, or take the dirty secret five-patty burger challenge at Misty's Diner, with its unashamedly zipper-straining American menu.

Parlour Diner, 64 Chapel St, 9533 2006
Babu, 156 Chapel St, 9510 6485
Huxtaburger, 203 High St, 9417 6328
Misty's Diner, 103-105 High St, 9510 1959

Dinner

Windsor really comes alive at night, so you're spoilt for dinner choices. For a rock'n'roll vibe, great tunes and a matching menu of guest beers, tacos and spicy fried tenderloins, head to Yellow Bird. For quick, fresh Mexican in a bright, casual dining hall, take a seat at Fonda Windsor. For pierogi, goulash, Polish antipasto and an encyclopaedia of vodkas in an ornate setting, go to Borsch, Vodka and Tears. For super-stylish Thai food that's not afraid to turn up the heat, the understated Ayatana is a great option, or for an intimate, rustic Italian experience, Franco Choo's swiftly changing seasonal menu is as elegant as it is flavourful. Orange, a long-time staple of the Chapel Street dining scene, is still a reliable spot for its hearty, meaty mains and pretty outside dining area, while The Woods Bar and Kitchen puts a deft spin on its US-leaning menu with spicy baked pork ribs, bourbon-laced brisket and fried okra (not to mention its swoon-worthy cocktail list).

Yellow Bird, 122 Chapel St, 9533 8983
Fonda Mexican, 144 Chapel St, 9521 2660
Borsch, Vodka and Tears, 173 Chapel St, 9530 2694
Ayatana, 97 Chapel St, 9533 8813
Franco Choo's, 179A High St, 9529 7310
Orange, 124-126 Chapel St, 9529 1644
The Woods Bar and Kitchen, 108 Chapel St, 9521 1900

Last drinks

Windsor is the polar opposite of a dry county, so you can enjoy a wee tipple at almost any establishment on the street. If you're a serious, old-school cocktail lover, Kid Boston's menu takes a classic, educated approach to its drinks menu as well as its dining options, while the newly opened Boston Sub includes a small cocktail bar at the back. The Smith has a small, perfectly crafted range of house-designed drinks, like the Toorak Princess, a gin-based cocktail with smoked hay and agave. For a velvet, loungey experience, head to the flocked and upholstered Back Bar behind Tusk, or for a more neon, pop time with Japanese snacks, the bottle slingers at Mr Miyagi can mix a mean drink. Then again, for a no-fuss, BYO-food-while-you-have-a-drink, the down-home Chapel St Cellars allow you to buy your drinks off the shelf and enjoy them at one of the laminex tables in store – with your own snacks.

Kid Boston, 44 Chapel St, 9939 5256
Boston Sub, 96 Chapel St, no phone
The Smith, 213 High St, 9514 2444
Back Bar, 67 Green St, 9529 7899
Mr Miyagi, 99 Chapel St, 9529 5999
Chapel St Cellars, 89 Chapel St, 9533 7769