A sloppily cuffed jean. An ill-fitting blazer. A dress that shows just a little too much to be referred to as “tastefully sheer.” These are the things that fashion editors and stylists can spot from a million miles away. To those in the biz, the proper proportions of a crop top may be obvious, but for those seeing the trends in a magazine or online, it can be a little trickier to know exactly how to wear everything.
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“How can I tell if my jeans fit properly?” “What’s the most flattering shoe?” Both totally reasonable questions. With. Answers.
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Ahead, you’ll find advice from celebrity stylists who have been solving fashion conundrums for years. And we’ve taken notes from a few of our favorite iconic style stars—Jackie O, Bianca Jagger—and made some inferences ourselves. Here, 50 fashion tips that have withstood the test of time.