The Athletic asked its NHL writers to name every NHL team’s best and worst jerseys, and I can’t complain with Max Bultman’s choice for the Red Wings’ best one (though I think that the Wings’ “regular jerseys” are the best)…

Best: 2014 Winter Classic
The Red Wings’ main uniforms are iconic, likely why they don’t have many alternates (and rather bland ones when they do). But the 2014 Winter Classic jerseys were sublime, incorporating history and legacy with a distinct look that jumps off the sweater. We’ll see what Detroit has planned for its centennial season, but these will be hard to top.
And Bultman’s “worst” Red Wings jersey is actually, well, this:

Worst: 2021 Reverse Retro
It’s not the most offensive-looking jersey in the world, but it’s so boring. It’s hard to go wrong with a logo as good as the winged wheel, but this jersey puts that to the test by doing basically nothing else. Frankly, it looks like a practice jersey. — Max Bultman
I can’t discuss any Red Wings jersey without pointing out that the Red Wings’ “Detroit Falcons” jerseys worn again in the 1991-1992 season are in fact the best alternate jersey:

Why mess with perfection?
Anyway, The Athletic’s story continues at significant length (paywall)
Best for me was the 2002 CCM white jersey. Those thing were thick and well made feeling like a hockey sweater unlike the Fanatics crap which are so flimsy now a days. Also, there was no stupid NHL logo on the front collar (which is one negative for me when it comes to the 2014 WC jersey) or the unnecessary laces. Once Reebok took over they had to add stupid things like the V shaped neck collar and of course the tacky NHL logo right in the middle.
As far as the worst, the 2022 red/black barber pole jersey is up there for me. The 2021 was boring and bland, but at least it didn’t look like a Blackhawks jersey. I hope to never see black on our jersey ever again.
Underrated jersey for me is the Centennial Classic with the silver stripe that had the Cup winning years on it. Plus I really liked the silver outline on the winged wheel.