Maybe they could improve their marketing message, but I doubt most wannabe Common Lisp developers are willing to pay for comercial tools, with enterprise prices, even if they had the best marketing of all times.
The IDE is based on their native GUI backend. Thus it picks up much of the looks of the current OS automatically (windows, buttons, dialogs, ...).
Though I'll propose it to them for the next LispWorks release...
Missing 5 Windows releases is just sloppy: Vista, 7, 8/8.1, 10.
I'm not saying it's a bad product, just that first impressions matter. There's a reason this site is full of discussions about conversions and funnels.
As a side note, Windows is also 30+ years old. Hardly new tech these days ;)
I can bet that LispWorks' customers (big companies and experienced lisp users) are largely away from the mainstream desktop world, and wouldn't care too much on how the current Windows UI looks like.
The IDE screenshots for Windows show off Windows XP.