On Location: Sydney

At first glance, the city looks like a slice of London haphazardly spooned into Southern California, as palm trees and bronzed shoulders share space with fish-and-chip shops on streets named Oxford and Liverpool. But a closer look reveals that Sydney-siders are unfazed by such a duality and navigate easily between the casual and the cutting-edge.

Playing host to such events as the annual Gay and Lesbian Mardis Gras and the 2000 Summer Olympics, Sydney has shown that it can easily move from the universal to the ultra-specific. And lately the ultra-specific has become universal, as more and more local designers are gaining worldwide nods. Names like Akira Isogawa, Lover, and Ksubi (formerly Tsubi) have all helped to put Sydney on the fashion map. But while high style rules the picturesque streets of Paddington, vintage and as-of-yet unknown designers monopolize the artsier Surry Hills area.

Centered around the bustling Crown Street, just off of Oxford, Surry Hills is brimming with activity and buzz. The sidewalk cafés are always crowded, and every block is home to a handful of stores worth a peek. Here, we've rounded up a few that are not to be missed.

• Cream on Crown, 277 Crown Street, +61 (2) 9331 5228

Cream on Crown's window display features decked-out male and female mannequins wearing blue and black striped duds, red suspenders, and matching Wayfarers, all in front of a huge backdrop depicting the cover of Joy Division's Unknown Pleasures. The '70s/'80s vibe continues inside where the owner Jonathan stocks his racks with bright, patterned vintage for both men and women from the U.S. and Japan. The colorful shirts and dresses are off-set by the rack-tops crammed with hand-picked vintage boots brought back from the UK—from slouchy to ankle to sleek knee-highs. Topping it off is a selection of deadstock sunnies—a stylish accessory necessary for stepping out in the southern hemisphere.

• Grandma Takes a Trip, 263 Crown Street, +61 (2) 9356 3322; www.grandmatakesatrip.com.au

Walking into Grandma Takes a Trip is like entering the organized-by-color closet of the most stylish and sophisticated grandma ever. Opened by Nicola Sault, who has a vintage collection comprised of over 8,000 pieces, the store reflects its founder's affection for the timeless fashions of decades past. The clothing here has a more polished feel, focusing on classic cocktail dresses complemented by proper hats and purses. Besides vintage, the store also offers Handcrafted by Grandma, a precise line of dresses, onesies, and shorts—as well as limited edition, one of a kind pieces—that are fashioned from vintage fabrics.

• Dobry Den, 326 Crown Street, +61 (2) 741 123; www.dobryden.com.au

If you're curious about what's of-the-moment in young Sydney, this is the place to go. Owners Keira and Nicole have created the ultimate den of hip, showcasing the wares of about 20 up-and-coming designers from Australia and New Zealand such as Friedrich Gray, Katou, Cybele and My Pet Square. From cute, kicky dresses by Kate Hurst and slouchy tunics by Alpha 60 to a wide array of men's T-shirts plastered with skulls and/or stripes, this is a shop that completely captures the spirit and style of the kids of Surry Hills.

• Kawa, 348a Crown Street, +61 (2) 9331 6811
A relaxed and friendly atmosphere with great people-watching tables outside on Crown Street are what make Kawa the perfect café to stop in for a bite or a coffee with friends. Most of the food is organic and put together in inspired ways (like the granola with poached fruit or the scrambled eggs with avocado). Be sure to try a Flat White, which is similar to a latté, but the milk is folded into the lower layers so there is only a thin foam on top.

• China Heights Gallery, L3 16-28 Foster Street; www.chinaheights.com

Switching from an opening a week to three a month in 2007, this DIY art space boasts shows from undiscovered local talent to international art scene darlings. Openings are Fridays 6-9 and there are always free drinks (to amp up your purchasing power, of course).

Further up from Surry Hills, Oxford Street leads into the village of Paddington. The shops here start to take on a little bit less of an edge and a little bit more refinement, as do the people roaming the streets. While there are some places on Oxford to check out, a real treat is a walk down the small William Street, which is packed with small boutiques, offering an impressive education in Australian and International style.

• Incu, 256 Oxford Street, +61 (2) 9331 6070; www.incuclothing.com

Twin brothers Vincent and Brian Wu debuted the first Incu in 2002 and the second in Paddington soon followed. "My dream was to open a little shop stocking clothes that I would wear," Vincent says. "I know I always hated wearing a suit in the office...I mean, what's with the tie?" There are definitely no ties in Incu, which is anything but a "little shop" and specializes in the best street-wear, much of it from Australia and New Zealand. From the more well-known like Marc by Marc Jacobs and A.P.C. to the edgier Raf by Raf Simons and Umbro by Kim Jones, as well as local labels such as Lover, Karen Walker, and Ksubi, the Wu brothers have covered all the bases when it comes to fashion-forward street style.

• Shag, 34 Oxford Street, +61 (2) 9357 2475

Situated close to the border between Surry Hills and Paddington, Shag is a unique merging of the two neighborhoods in one engaging shop. Every rack is packed with vintage wares as well as pieces from independent designers in Hong Kong. The owners regularly make trips around the world to fill up on angelic, '70s party dresses and bat-winged tops (all sans tags). Shoes are crammed in everywhere, spilling over from the top of the racks onto the floor.

• Pelle Recycled Designer Footwear, 90 William Street, +61 (2) 9331 8100; www.pelleshoes.com.au

Seriously a shoe-freak's dream come true. Owner Monica Schnieper has collected only the best vintage and designer specimens (very lightly worn) for consignment. From electric '80s pumps to timeless snakeskin Dolce & Gabbana stilettos, there is a perfect pair here for everyone. Despite its tiny quarters, the shop's rows of shoes are seemingly endless and impeccably merchandised.

• Belinda, Belinda Menswear, The Corner Shop, 39 William Street, +61 (2) 9380 8728; 29 William Street, +61 (2) 9380 8873; 43 William Street, +61 (2) 9380 9828; www.belinda.com.au

Belinda Seper is something of a local fashion-world celebrity in Sydney. This one-time model opened her first boutique in 1992 and nine more have followed, three of which are in close proximity to one another on William Street. Her eponymous accessories store carries an enviable mix of purses and shoes from labels like Marc Jacobs, Miu Miu, and Costume National. Over at The Corner Shop you'll find fresh brands for the rest of your outfit from lines such as Mint and A. F. Vandevorst, which are housed alongside Australian up-and-comers Lover and Willow. There's also denim from Imitation and Superfine. And though they're not represented here, men will find offerings from the likes of Martin Margiela and Ann Demeulemeester at Belinda Menswear where even the décor takes on a more masculine feel.

• Sloanes Café, 312 Oxford Street, +61 (2) 9331 1070

Stop in at Sloanes for the café-style food (including all-day breakfast) and take a break from the crowds on Oxford Street. There's also a back garden for kicking back and enjoying hearty soups and salads, or just a cup of their extremely good coffee.

• A Fish Called Paddo Seafood Emporium, 239 Glenmore Road, +61 (2) 9326 9500
Located in the Five Ways, a convergence of five roads in Paddington, this restaurant has taken fish and chips to a more refined level. Fresh fish is offered in every way from sashimi to grilled to the traditional fried (served with chips). Though the fish can't be faulted, it is the chips—cut thick and fried to a perfectly crisp finish—that really stand out.

Refinery29 checks out the neighborhoods of Surry Hills and Paddington.