It's a difficult argument to make, we realize, but there's something to be said for owning your own tuxedo. It's the type of guy we should all aspire to be—prepared for any situation—who shows up looking dapper yet comfortable. "There's a certain ease and confidence that comes with wearing your own tuxedo," says Jack O'Connor, Men's Style Director for J.Crew. "You have the freedom to take it to your own tailor so it can truly fit your body. After all, you want it to feel as great as your best suit." Here, the man who styled this black tie look (along with the inspiring looks in the company's catalogs), offers some tips to avoid the dated accessories and details that usually come with a rental.