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The best way to experience Kowloon is to willingly let the mass of humanity guide you through the main streets like Nathan Road, Jordan Road and smaller narrower streets like Mody Road or Kimberly road. The most wonderful thing about Hong Kong, to note, is that locals make up most of the population so unless you are at some expat enclave in Central, Stanley or Sai Kung, it's likely you'll always be surrounded by locals of all types. This makes it a much more real experience.
In general shopping options range from local food, tailoring, electronics (cell phones and cameras), clothes and shoes. Many tiny clothes stores sell high-end fashion abound. Side streets make for great strolling as well. Here you can find tailoring services, available ranging from $200 to 600 per shirt for the inclusive cost of fabric and tailoring. You can also take your own design to have tailors make replicas for you.
Mody Road is one of the most interesting streets, it leads into a curious little alley that has about a dozen extremely high-end restaurnats and bars serving a wide range of international cuisine. Delve deeper into the maze of alleys behind and you'll find karaoke's and pubs and of course more shoes, electronic and clothes stores.
At Chungking Mansion, there is a lot more people watching, as you enter this other world. You will see currency exchanges set behind iron grills, Bollywood dvd stores, South Asian restaurants, cheap motels and their touts trying to rent you rooms. Even immigration lawyers can be found here. The Indian food in the vendor-style restaurants is authentic even if hygiene is slightly questionable.
Farther along in Jordan, the main street intersecting Nathan and opens into Canton street. Light Vegetarian Restaurant: right beside Jordan MTR,excellent vegetarian dumplings
Temple street, which is perpendicular to Jordan is a very touristy street. Avoid the night market for shopping as the only shoppers here are tourists, the goods on sale are very mediocre and can be found anywhere in Hong Kong. But temple street offers excellent hawker food with English language menus. The outdoor ambience is very lively and exuberant. One eats in the company of locals, sometimes next to people who bring their own bottle of scotch or VSOP.
In the markets there there some things to keep in mind: 1. You can try out pants and skirts and shoes but no upper wear. 2. If you try something, you should be fairly sure you want to buy it. 3. Rates are very competititve, in general rates will be identical if stores are on one street.