The Italians call it sprezzatura. The French call it elan. Magazine editors call it "effortless dressing." Whatever you call it, stylish dressing does not come easy, but the somewhat herculean task is to make it seem that way. Any fashionista knows that stylish dressing is a craft that one hones after extensive experimentation. So how does one accomplish this?
1. Know what works for your body type. For example, I always look good in something belted, rather than a drop waist. As a result, I invest in decorative, expensive-looking belts. Knowing your own body type helps you avoid looking ridiculous, and it saves time from trying on trends that don't work for you.
2. Invest in quality items that you will wear over and over again. A cropped, neutral leather motorcycle jacket that fits you like a glove. Those killer jeans. That stand-out piece of jewelry. Instead of saving them for a special occasion, pull those items out frequently, because you know you look fabulous in them no matter how disheveled you feel.
3. Work on creating winning combinations. Find the silhouettes that work for you. (Jeans, jacket, decorative top. Cardigan and skirt. Dress and pumps. Repeat.) Experimentation first thing in the morning is what makes you look like you tried too hard, because chances are, that look is awkward.
4. Simplify, simplify, simplify your closet. Donate items you don't wear or that look awkward. I can't tell you how many times I've held onto an item that I can't figure out. Every time I experiment with it, I come to the same conclusion: it doesn't work for me. Organize your closet by type (jackets, skirts, dresses, etc.) and by dressiness (casual, work, occasion). A complicated closet lends itself to a complicated look.
5. Pay attention to your shoes. The wrong pair of shoes can ruin your entire look. Personally, I think flats look wrong with a pencil skirt, and high heels look wrong with a very short dress. Again, know what works with the combinations you've pre-established.