Beauty is such a subjective thing that everyone is going to disagree with everyone else's choices. One persons ugly is another persons hometown, and will be defended to the death it seems. Even so, some cities are prettier than others. Here is what my eye beholds:
Ugliest City: Newcastle, New South Wales.
Newcastle is an industrial city about 2 hours drive north of Sydney on the New South Wales mid-north to central coast. Looking north across its port from the city are the ugly remains of refineries and other former industrial glories from years past. The last time I visited, residents of the city abandoned their own city centre in favour of suburban malls and outer city entertainment venues. Its like a ghost town at midday. What buildings that are there are pretty typical of an industrial city, with more thought given to function than form. Despite Newcastle being the ugly duckling of the nation, its residents are also its rough diamonds - weathering storms and supporting their local community in many ways that would leave prettier cities to shame in their wake.
Prettiest City: Perth, Western Australia.
Perth is pretty is so many different ways and places. The 640 hectares of the enormous Kings Park in the most prized real estate in the city provides the most scenic views of the Swan river and the most beautiful natural parkland (much of if open space since colonial times). The vast majority of the worlds most beautiful orchid flowers can be found represented in Kings Park's botanical gardens and throughout the city. The city lays claim to being the Art Deco capital of the world. Should you look above the shop awnings, every where you will see examples of beautiful Art Deco facades and architecture (Hay and Murray street malls particularly). Elsewhere you will find mixes of the ancient and the new. Fremantle is a treasure trove of beautiful colonial buildings and rejuvenated woolstores and port buildings. From afar the Bankwest tower is a glass curtain reflecting the city surrounds. At street level it is the facade of an old worlde pub with the most beautiful restoration work both inside and out, all of which complete hides the modern structure towering behind into the stratosphere. Even on the wrong side of the railway tracks in Northbridge, you will find beautiful open spaces, Art Galleries, nightclubs and lazy manicured tree lined streets. It doesn't seem to matter where you go, Perth has both a modern and an historical beauty that in my eye is the prettiest in the country.