In my financial counseling practice, I use the rule of thumb that a reasonable amount to spend on clothing without overspending is 4% to 6% of your take-home pay per month. Just take the number that your paychecks actually add up to in a month, and multiply that by .06 Just remember that this amount is for the entire family, not just one person unless you are single and no one else is depending upon your income.
To start with I don't think $500 is enough for what you listed but, at the same time, I think you're spending too much at once. I believe that clothes shopping should be a regular experience and not a once a year experience.
I would plan to make one purchase at a time. Once or twice a month, depending on what you can afford and your pay schedule, you should go clothes shopping. Each time you shop you should buy one outfit.
Then, I would go for the jeans and the black sweater. Jeans can cost between $25 for basic Levis to $200 for designer jeans. Try to stick to the $60 range. Take your time and search for jeans that really fit you. It's not as easy as it sounds. For the sweater I would buy cashmere. No other sweaters wear better and look great for a longer time than cashmere. If you're thrifty you can find one for under $100 but it will take some shopping. Winter is the time to buy cashmere so don't wait too long because spring clothes will be coming soon. I make a point of buying at least one, if not two, cashmere sweaters each Christmas season.
I always maintain 5 pairs of jeans and just buy a new pair when one of the 5 becomes unwearable for some reason. I always have no more than 5 pair and no less than 5 pair.
Spring - This is a big time to shop. Spring is when fashion colors change again and it's time to buy dress pants with matching or complimentary blouses. It's also time to buy a new purse in a lighter color that compliments your spring clothes.
Summer - It's time to buy play clothes for outdoor activities and be sure to buy a light summer dress. They are a must for light wearability and going out.
every woman needs 10 basic wardrobe pieces as the basis for style. They are:
1. A good fitting pair of jeans
2. A white shirt
3. A blazer
4. A trench coat
5. Dress pants
6. A skirt
7. A basic black cocktail dress
8. A sweatsuit alternative - clothes to be active in that don't look sloppy.
9. A cashmere sweater
10. A dress (I can't remember how he described this dress but it's not too formal, maybe a business dress)