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Packing for a vacation to the city can be tricky.  Here's some questions to keep in mind when packing for your next trip to a big city:

1. What season is it?  If it's cold out there, you're going to need to pack some good looking warm clothing.  For example: a few nice pairs of jeans, a pair of slacks, a few nice sweaters and/or long sleeve shirts with undershirts, a hoodie or sweatshirt, and a waterproof jacket just in case it rains.
2. What activities will you be partaking in?  If you plan on seeing some shows or going to nice restaurants while you're in the city, I recommend bringing some nice jeans or slacks and nice shirts/sweaters. 
3. How much do I need to pack?  In terms of underwear, always pack 1 for each day you'll be there with 2 extra just in case.  Otherwise, pack a full outfit for every day you'll be on vacation, with the exception of sweatshirts and jackets (you only need one for all outfits). 
4. How should I pack my suitcase?  Usually, when traveling to a large city you'll be staying in a hotel.  So, pack however you'd like, as long as everything fits.  I recommend situating your suitcase for easy unpacking: underwear and socks on top with belts, shirts next, then sweaters, then pants.
5. What about shoes?  Depending on how long your vacation is, and if you're attending a nice venue, I recommend packing a pair of comfortable walking shoes along with a pair of nice shoes to wear to a show or nice restaurant.  Flip flops aren't good city shoes, so if you need a pair of sandals or flip flops then check the closet, some hotels offer slippers.
6. What toiletries should I bring?  Most hotels offer soap, shampoo and conditioner, as well as lotion.  So, to save room I suggest packing these simple bathroom necessities: toothpaste, toothbrush, face wash, cologne (optional), moisturizer (optional), Qtips (optional), razor, shaving cream, and deodorant.