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I'm no expert, but in my opinion the quality comes in the construction and materials used. I've seen some Newsboy caps that looked like they were assembled by someone who was still learning how to sew--uneven panels, seams that were "bunched up", brims that were offset (i.e., not properly centered on the front of the cap). If you read through some of the Newsboy/Flat Cap threads you'll see quite a few vendors mentioned repeatedly such as Hat People and B! Wear. I've never purchased from B! Wear myself because I don't particularly like the narrower brims they use, but they have quite a few fans here who praise their comfort and construction. I can vouch for the quality of Hat People's caps; I have two currently, and will likely purchase more from them in the future.What makes a quality new boy cap?
The crown of a traditional Newsboy cap is comprised of eight panels, usually topped with a button where the seams intersect at the top of the crown. Wool is quite common, but I've also seen linen, cotton, denim, and leather used frequently. I would imagine just about any durable material could be used as a matter of personal preference. Satin and cotton seem to be the most common for the liner material.I thought I read something about the number of panels. What about the material. It looks like wool is common.
As for the shape...well, as this thread illustrates, that's also a matter of personal preference. Some, like Marc Chevalier, prefer the more traditional "flat" look, and I think that shape suits him (and many others) very well. I prefer the more modern "floppy/saggy" look myself.
You might also consider looking at "Ivy" caps, another popular style of flat cap. Similar to Newsboy caps, they're generally a bit flatter and narrower. I suggest this only because I have a very good friend I've known for nearly 40 years now, and we both agree Ivy caps suit him better than Newsboy caps; conversely, we also agree Newsboy caps suit me better than Ivy caps.
Above all else, I would suggest you visit a hat shop to try on different styles and colors of flat caps to see which work best for you before making a "blind" purchase online. Speaking from personal experience, any cap can look good in a photo; whether or not it looks as good on your head can be a different matter.