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A guy who carries himself like he has nothing to prove can wear a $300 Seiko and look like he's worth ten million dollars

Whether its a Valentino cutout floor-length gown or an Azzedine Alaa micro mini, Aniston has consistently reworked the look over the decades, mixing it up with different textures and silhouettes to keep it fresh

Of course, if you are an expert, you could play with subtle and non-traditional shirts, as long as they're very subtle and you avoid wearing them with a printed blazer

How far you want to push the limits of the cocktail dress code (or any dress code, for that matter) is really up to you