Maybe it's the way it's designed or the shape of his mouth. Just doesn't look awesome.
shareI like him just fine as Matt, and the costume looks pretty good, but yeah, there's something unflattering that happens when his face meets cowl.
shareHe looked awkward in the season 1 cowl because it wasn’t a good design.
http://static.comicvine.com/uploads/original/6/60273/4735714-0214354290-scree.jpg
But he looked badass in the season 2 cowl. It was much better tailored to the shape of his face.
http://screencapped.net/tv/daredevil/albums/season2/dd209/dd209_3253.jpg
http://screencapped.net/tv/daredevil/albums/season2/dd207/dd207_1001.jpg
http://screencapped.net/tv/daredevil/albums/season2/dd207/dd207_3804.jpg
http://screencapped.net/tv/daredevil/albums/season2/dd207/dd207_3803.jpg
Looks like some things that were improved were: The seams above his eyebrows in the original suit were taken out. They made him look like he was arching his eyebrows all the time. It was a strange choice. His eyebrows are more pronounced in the second suit. The horns were enlarged. Can't put my finger on what else was improved, but it does look a lot better.
There's still room for improvement, though. Hopefully, in The Defenders, he'll have another upgrade.
"When you gaze into the abyss, the abyss gazes also into you."
Agreed, his mouth made him look like he was squinting. Second mask seems a little better for him
shareI was beyond thrilled when Matt first wore the suit at the end of season 1, thus I found nothing wrong with the mask's design. Looking back, it was a rather poor design and it looked unflattering BUT keep in mind it was, well, his first real costume.
As for the one in season 2, frankly I love how it looks. In fact, when I see Charlie in it I just can't picture another actor looking more badass as Daredevil. They could always improve things, sure, but I wouldn't mind if he didn't show up with a new one in The Defenders.
You want something corny? You got it!