When it comes to myriad issues I have with the Band as a product, comfort and looks are not one of them. When it's on my wrist, I don't notice it - never did. Maybe it's because I always wore watch my whole life and therefore the Band does not really bother me. I do have issue with the design that is too rigid, resulting in having three sizes (which is ridiculous thing if you think about it) and some wrists just not conforming to the band at all. Specifically women with small bony wrists can't wear band even in the small size.
As for the looks, besides display that is easier to scratch then even $20 cheapo Chinese electronic watches, the rest of the package, if it sits on the wrist properly is actually quite nice. I wear my Band face down (the only way to comfortably read the text on that long horizontal display) and so others mostly see one continuous matte black band on my wrist that is not too thick and clasp that blends very well and adds some design detail on the otherwise unnoticeable product.
I can easily see why many would not find Band comfortable or good looking. It all really depends on the person's wrist. If it works, it works, and if it doesn't, folks would not like both comfort and look.
Though I understand why MS chose the design they dd (to add battery capacity on two sides of the wrist and to place HRM opposite of the watch to reduce overall thickness) Microsoft should rethink the design for the second iteration to get rid of size-specific bands and rigidity. Hopefully, better technology would allow them to do what they just could not do at first.
I think Apple would lead the way for now with the design and we should see other companies quickly falling in line and copycatting what works (Samsung, I am looking at you ;-))