A bit of background before the meat of the subject, this was one of the earliest designs of my avatar as seen in this submission https://www.weasyl.com/submission/416821/tails-likes-cucumbers . As a matter of fact, his first design and concept was just an alternate timeline of Tails who wore a scarf (and had developed a strong hatred of Sonic. Yes how Mary Sue of me :p)

That said with the new Sonic Boom character designs, I thought this harmless jab was necessary, if just for the humor of it (after all, if you can't laugh at yourself...). I'm rather indifferent towards the designs but I do think Sonic wears the ascot pretty well (although I think it could stand to be a brighter color other than the browns used)