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How do you like to dress? Are you wild or more conservative? Do you prefer business formal or casual comfort? Is your current wardrobe classically elegant or fashion forward? Consider the persona you want to present to the world.
Your age. Clothing should always be age-appropriate. If you've got grandchildren and you're dressing like them, there's a problem. It's OK to want to look youthful -- just make sure your outfits suit your stage of life.
Your occupation. You wouldn't wear jeans and a cut-off T-shirt to work at a law firm, and you wouldn't wear super-high heels and a short skirt to teach kindergarteners. Use your profession as your guide when you shop. Once you've got an appropriate ensemble for your job, jazz it up with a few accessories to add your own personal flair.
Your lifestyle. Stiletto heels are just fine for the city, but they'll make you stick out like a sore thumb if you live way out in the country. Fashion should combine form and function, and it should fit well with your surroundings.
Remember that you don't need to buy designer duds to express your personal style. Even jeans and T-shirts can be stylish if you feel comfortable in them and choose the right ones.