Known as a city of great natural beauty with its beaches and sporty, sun-drenched way of life, Sydney surprised me with the level of chic style to be found in the bars, restaurants, and shops lining its famous harbor. Likewise, there's a level of luxury available that’s unexpected, given the laid-back seaside vibe. You'll encounter more people in good moods than anywhere else in the world.

THE SARTORIALIST, Scott Schuman.

Sydney's signature surfer style tends to spawn expectations of laid-back dishevelment. So it can be surprising to see how chic people in the city are—heels, burnished shoes, the whole nine. Don't let the perception lure you into a lowered state of Sartorialism.

If you choose to rent a car, try to plot your routes before you buckle in. The streets in Sydney can be confusing—and not just because of the drive-on-the-left-side custom. At least the motorists are usually courteous on the roadways.

While proper beach attire generally reflects what you’d expect to see in the States, it’s not uncommon to stumble upon a topless—or totally nude—beach. Want to let it all hang out? Just follow the lead of more daring beachgoers.