First as for time to go- it will be less crowded if you go in the winter but while it will be less crowded but it will be so much more depressing (think darkness at 4pm). It does not get 'warm' and I use that word loosely until May so if you want to have nice strolls May through September I think is your best time to go.
Now for my spew of knowledge....
First for the ladies, shopping!
-I am American and therefore will always have a love for pretty malls. London did not have any fantastic malls (in my opinion) until recently, Westfields (yes they are all over America). The reason I think it is great is because it has all the cute little UK stores in one undercover location (good for rainy days). This way if you are looking to pick up some clothes or shoes that you cannot get in the USA, you can find them all under one roof. (Although now that Asos.com is in America you can get a lot of it on line!). Take the Central line to Shephards Bush and you cannot miss it.
The other reason that Westfields is a must is simply that Oxford and Regent St (while massive tourist locations) are horrible to actually do any proper shopping on. You are walking on super crowded streets with the stores spread down many many blocks with crappy little stores in between. You are held up by street crossings, bombarded with people passing out fliers, and if it is raining it is even worse. Of course Selfridges is on Oxford St so you will most likely have to brave a bit of crowds regardless!
Oxford Street at Christmas
-For more unique shopping you have many many options in London. Notoriously there is Camden (worth seeing for people watching but unless you are into pleather you wont be buying much). The other big tourist shopping street is Portobello Road. It becomes absolutely slammed by noon so the earlier the better. It requires serious hunting to find a good deal but they are there. Particularly portobello green (if you are coming from nottinghill it is at the other end of the market and under the underpass) has loads of good places to get fascinators or hand made jewelry. Take Central Line to Nottinghill Highgate.
Meanwhile Kingly Court (off Carnaby street which is in turn off Regent St) has loads of kitschy shops as well as some good boutiques. It also has a nice little cafe which serves candy cakes (giant cupcakes with very bright icing). Traffic people (http://www.trafficpeople.co.uk/shop/?gclid=CJ2O5efu5asCFWJn5QodKSUdJQ) is a particularly good store for getting a little something for going out in.
Finally for clothing and accessories there is Spitalfield's market near Liverpool street. Go on a Sunday as the things displayed in the market change daily. Things I have bought at this market include a hand made coat (when I tried one on and thought I might need to go a size up the man actually said 'o no I made a few smalls smaller than the others', proof he made them, a dress made out of men's suit jackets and ties, and a rather cute t-shirt. Other days it is an antique market, art market etc. To get a full schedule go to :http://www.spitalfields.co.uk/
As for food you must go to Borough market (from London Bridge tube station), Thursday is the best day to go (and avoid lunch time to avoid the lunch crowd unless you are also looking for lunch). You are unlikely to buy something (although there is an excellent beer shop) but it is a worth looking around and sampling some of the fares. If you are keen to eat there for a meal it is a great idea, you can get a super cheap and amazing meal in the market itself if you are on a budget or you can go to one of the many restaurants surrounding it (they pretty much all use fresh, local, food). I have eaten at (and loved) fish!, roast, feng sushi, and the oyster bar and not been disappointed. There is also a tapas place at the head of the market (http://www.brindisa.com/), it is legit tapas (has special catalan dishes) but it does not take reservations and is always packed. (It too is amazing but if you want to plan in advance might not be worth it).
That is it for shopping up next will be my second favorite activity - eating.
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