Sometimes a company can impress you despite your first impression.
I buy shoes at this place. They have nice staff. They know what they are doing. They are considered experts locally. Their service is super.
But their website is like a flashback to 1994. Or rather, they built the website in '94 and have never done a redesign to bring it up to modern technological or aesthetic standards.
While a business that still rings up sales on an old cash register (Cha-Ching!) can appear quaint and nostalgic, an outdated website suggests cluelessness.
It lowered my expectations as a first time customer.
While the 'retro' website may be an in-joke for regular shoppers, how many potential sales are chased away?