There are people that have even travelled the world packless, instead relying on cargo pants and vest/jackets with plenty of pockets.
Anyway, you are in a "wrong" forum but many things from this site can be applicable to your trip. Since you're focusing on clothes in this post, so will I. Also much of this is going to sound "radical" and these are merely suggestions for minimizing weight and excess clothing. If how you look plays a role, you may keep certain items regardless of what pure pragmatism would dictate, and since you're in civilization
1) Avoid cotton at all costs, this is includes denim/jeans. It is slow to dry, holds lots of water, and does not keep you warm when wet. Cotton is also really heavy, a pair of jeans can weigh over a pound. Instead wear synthetics, down or lightweight wool.
2) Wash your clothes daily. If you do this you won't need 5 days worth of jeans, socks, or underwear. Wash one pair in a sink and let it dry over night. You'll have fresh intimates in the morning and only need to carry two of any type of clothing (although most clothes doesn't need washing daily).
3) Ditch the leather jacket. This may be the hardest thing, I know retiring my leather jacket was a sad day. For warmth you'd be better served by a light down or synthetic insulated jacket. Leather also isn't water proof and you'll probably want either an umbrella or rain jacket anyway. Montbell and The North Face have some insulated jackets that are cut well for women and should pass the city fashion test. Alternatively many of the softshell jackets available are great for urban life. I replaced my leather with an Arc'Teryx Gamma jacket (pricey example but other softshells exist) and I have far better temperature regulation and water resistance now by adding extra shirts for warmth.
4) Your shoe choices should be fine. Unless you're going really formal the ballet flats should work as "nice" shoes.
5) Rain protection: I mentioned it before, but it's worth pointing out again. So far you have very little, and if you're backpacking you'll want the security. You can go hideous and cheap with froggtoggs or driducks ($25) or go up to around $100 for something that actually looks like it was meant to be worn by people. People do take umbrellas backpacking and some light options are made by GoLite.
Hope some of this helps. Also read the Backpacking 101 guide. A lot of the info is outdoor backpacking specific, but the concepts are just as applicable to light weight travel (and honestly most of the gear/clothing overlaps between the two pursuits). Buy a scale and start weighing your clothes. You'll be surprised at what "feels" light but really isn't. Looking at your list I wouldn't be surprised if you've already put in around 7 or more pounds in just clothing (there are people who have all their gear: clothes, sleep, shelter, cooking, toiletries and backpack weighing in at less than what you'll be carrying in just clothes). Try to minimize number of items that you carry focusing on highly versatile clothing, then bring the lightest item that fits that role.
http://www.backpackinglight.com/cgi-bin/backpackinglight/00034.html
You're enjoyment is paramount, but often you'll be surprised at how reducing what you have can raise your enjoyment levels, especially when you're feet aren't as tired and worn out as a heavy backpack will make them!
