Be (classically) adventurous
Do not fall back on the old styles simply because they are the kind of clothes you have always worn. See what is new; try them on. Find out if the new styles will work for you and the kind of life you lead. Ignore items that make a bold fashion statement but examine the new arrivals — jackets, cords, lightweight suits, cardigans, polo shirts, anything — in the better stores and boutiques.
If you have not already done so, try on soft tweed sports coats, the new-shape trousers, trenchcoats, the new sweaters and suits that cost far more than you would pay normally. And think when looking at them how, when and where you can wear them and consider if they can be worn in more than one way or up-date something you already own. Clothes should be versatile. A leather jacket, for example, probably costs a small fortune so you should make sure if you are buying one that you can wear it two ways: casually over a polo shirt or sweater and, more formally, with a shirt and tie. Try for garments that are practical as well as good-looking so that you can get reasonable mileage out of them.
It is by being far-sighted and adventurous with your clothes and by successfully mixing and matching shirts, sweaters, jackets and pants that your clothes begin to work for you. You will need less clothes and people will notice you for your stylish changes.
When revising your wardrobe select clothes knowing that they will work well with the other good clothes you already have.