Why? More like Why Not? He's Jeff Bridges, so he can wear the same shirt in three different films if he wants to. In fact, you can too. Here's the shirt; get yourself one. In fact, if you want an easy way to be Jeff Bridges for Halloween, may we suggest this shirt paired with a White Russian? Cheers.
What's impressive is the shirt's longevity (assuming it's the same one, which is unlikely). Its film career spans nine years: Cold Feet (1989), The Fisher King (1991) and The Big Lebowski (1998).