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T nagar is one of the most busiest shopping area in Chennai. If you are looking for clothes or jewellary what local people prefer, you must visit this place once. But the first thing to keep in mind before going here is that you need to be very careful about your belongings and dress appropriately ( for foreigners) so that you are not a target for eve teasers. Jeans and a T shirt would do, but skirts... you must make sure that it is long enough. People down south are still a bit conservative and dont really appreciate short skirts and spaghetti tops in public places ( unless you are going to a night club or a dinner in a good restaurant).
Ok now that you are dressed well for this place and made sure about safegaurding your money, credit cards and other stuff, you are ready for a walk in T nagar ( never have your rug sack behind you). Usman road is a big street ( always filled with people ) with lots of south Indian gold jewellary shops and Kanchipuram silk saree shops. The saree shops are like 3 / 4 floors showrooms which have sarees to door mats in amazing prices you are looking for. If you are not so knowledged about the prices its better to go to one of these bigger shops where they are always at a reasonable price. When you opt for silk sarees.. you have them from 1000 Rs to even Rs 1 lakh in some shops.
Next interesting place is the ranganathan street. This is one of the side streets in usman road. Its a full pedestrian street and here you get everything and anything cheaper. From dress materials ( salwar kameez - traditional Indian wear) to bathroom slippers. But for a first time visitor, its good to have a local person with you if you really want to make purchases or jus do a window shopping.
Its good to take autos or taxis and not public transport ( though they are very very cheap). The buses are mostly crowded and prone to pickpockets. Autos are a good soltion if you know how to bargain. Else there is always call taxis who go by meter and never rip you off. Always while getting out of your hotel, get a few call taxi numbers from the hotel.
Next to the usman road is Pondy bazar ( 5 minutes walk). Here you get lot of tinkets and, artificial earings and chains and lots of other stuff on the shops at the pavement. But you can survive here only by bargaining. Any earing start from Rs 20. But still it is better if you have a local with you while shopping. You also have big shops like naidu hall, krishna tulsi, sri krishna stores,hayagrivas and brands like raymonds and chain shops like globus. On the usman road, you have chennai silks, nalli, Sri kumaran silks, Rmkv which are very good shops.