One of the trickiest things about the art of costume design for movies and television is that it's not just about constructing fabulous garments or putting together outrageous outfits. The costume designer is also charged with putting together outfits that reflect the way real people dress and making sure they don't look like costumes.
Even for designers working in modern settings where this may seem no more complicated than a trip to the mall, the task is complex and requires making sure clothes fit the color palette of the film, look lived in and give the right subtle cues about a character -- from fit to style. Clothes that are too tight say one thing about a character; clothes that are too loose say another. And without a doubt, something perfectly tailored will help any character, and any person, project an air of success. The trick of costume design is often to figure out how to let the imperfections in a character's wardrobe shine.
For those designers working in historical contexts, the great challenge is to make clothes look authentic and not like costumes. One prime example of this was in Master and Commander, where the wool used to create military uniforms had to be distressed by exposure to seawater and salt in order to make the costumes look plausible.
Some costume designers take a different tact though, going more with what the audience expects to see more than what is historically accurate. The gowns worn by the emperor's sister in Gladiator are a prime example. Although they borrowed from ancient Roman fashion, they were very modern and looked more like Grecian-influenced casual wear and evening gowns than anything that would have been worn at the time. The audience was happy to accept this in the wake of other, more accurate costuming for other film characters. In fact, these dresses helped provide a point of access for viewers who felt they might not otherwise be interested in such a story.