For years, James T. Kirk boldly took us where no one had gone before. As captain of the Enterprise on Star Trek, he introduced us to new life, new civilizations and new adventures out in the final frontier. Kirk found himself in a lot of diverse situations during all these travels, and along the way that meant he had to wear quite a few different — and interesting — outfits.

Whether it was hosting a formal event on the Enterprise or going on an undercover mission, Kirk made some bold fashion choices as a member of Starfleet. Sometimes these choices were his to make. Others were out of his hands and forced upon him by the situation he was in. Either way though, many of them were memorable and some were definitely better choices than others.

Here are the 10 looks I think were Kirk's finest throughout the TV show and movies, counting down to the best.