[Jack smiles both at the sight and at the irony. Those clothes definitely suit Hiccup, even if the hoodie is kinda tight (which of course Jack's mind took care to notice, and not only because he favors hoodies). He wonders what his father would say about it. Meanwhile, the muggleborn is still wearing his school robes. It was weird at first, wearing wizard's clothes, but he got used to them quickly - they're more comfortable than they look. But the main reason why he likes wearing them is because they help with the feeling of forgetting about home and belonging to a new, better place.

This time he doesn't hesitate, he's telling himself again that there's nothing wrong with some friendly touching, so he gets closer and ruffles Hiccup's hair. Would he be allowed to help with the braid some day? He still remembers how to do it after his sister taught him.]

You don't look half bad in those, you know. [His turn to wink.] Thaaaat is a surprise. But I'll let you choose the how. We can sneak through a corridor I found ooooor you can fly us there. Which I think is the way it's supposed to be entered anyway.