I think that
@plainjaneFJC was possibly onto something with the comment re the desirability of retro inspired vehicles. Some have been great, some not so good.
I think there are some things that make a difference however in the desirability of them:
1) Consistent design cues, or at least evolutionary: Porsche are the masters of this with the 911 - similar proportions, same (rough) glasshouse shapes etc. VW on the other hand didn't get it as right with the New Beetle 1.0 or 2.0. Both Ford and GM have got this with the current Mustang and the Camaro, even the Corvette falls into the evolutionary on the whole.
2) Scalable design cues: BMW got this right with the MINI - the original was woefully out of date, but the new MINI was a great nod to the past, and has spawned some variants (some more successful than others) in the same way as point 1 below.
3) Audience: Knowing your audience and getting it right; BMW kept the MINI light and good handling, no matter what engine was in it. They also made it stupidly quick as a John Cooper Works. Chrysler with the PT Cruiser used a FWD, 2.0 4 cylinder engine... now imagine if it had had 4 litre + V8 in it and RWD - would it have been as criticised?
Things that don't work are:
1) Compromises to the base platform: the VW Beetle was spun off the Golf(Bora/Jetta)/A3/Skoda Octavia platform - all of which had 5 doors or a saloon version, and some a wagon
2) Performance mismatch to what is expected. Chrysler using the 2.0 4 cylinder and FWD in the PT Cruiser for example
3) Mismatch between target customer profile and actual customer. Manufacturers are great at this, they do it with all sorts of things; market them to 20 or 30 somethings, but the actual customer ends up being your 60 or 70 yo MiL.... Honda did this in the UK with the Jazz (US market I think they're the Fit) - quickest way to know that you're behind an old person is to find one of those...
Ultimately it's easy to get wrong when they're more style than substance; they need to live up to expectations and be suitably aspirational as well. It's why the 2.3 Mustangs never take off... and why the LR Defender may struggle. As an outsider, the Bronco ticks 1, 2 and 3 from the good list; the good news is that the American market doesn't get the Ford Everest (which is the Australian wagon version of the Ranger) as that might expose them to the risk of 1) from the 2nd list.