Honestly the average user should probably go wireless. The convenience factor is huge, and most of these new headphones come with active noise cancelling.
The average pair of wireless headphones is also good enough for casual listening (depending on codec) and can come pretty close to wired solutions.
That said, I would never go for wireless on ear/over ear headphones again. The more features something has, the harder it is to fix when something breaks.
My wireless solution is a set of mmcx in ear monitors connected via Bluetooth adapter. Even without active noise cancellation, they block out sound well. For desktop my job requires critical listening, and I like neutral signatures, so I'd rather stick to desktop monitors and wired solutions.