squiiiiiiirrel boooooooy
1. Okay, first up is the tail. Dean's tail is massive and fluffy. Ignore the fact that squirrel tails are normally bushy and wiry; Dean's is like a fluffy, cuddly blanket and looks almost cartoonish with how much it evokes "squirrel" - kind of like if his heart was shaped like ♥ instead of what an actual heart looks like. But with his tail. :D
Also, he now has squirrel ears instead of human ones! They sit higher on his head, like a squirrel's would (semi-accurate visual reference, though Dean's are bigger). His hair grew in to fill the space where his ears were. Not that it's come up, but he's pretty much only going to be able to wear ear buds from now on, instead of traditional headphones.
When it comes to facial hair, he's usually got a little scruff and stubble going on, but not overly much. He doesn't like the way he looks with a full beard (he's enough of his father's son that it didn't take him very long to experiment with that). As for build, he's on the short side of tall (5'10"), and is best described as lean and fit. He's too soft to be wiry, but he's not the muscular man so many others around NA are. Also, he matches his PB pretty well in terms of body fuzz: pretty much none. A very light dusting on his legs and forearms that isn't terribly noticeable, and no happy trail to speak of. It's like all his dad's hairiness got concentrated in his tail.
No tattoos, and his healing factor takes care of scars, too.
2. Dean's style is super simple, wearing almost exclusively jeans, t-shirts, and hoodies. He wears a lot of nerdy shirts, especially ones that feature or reference video games, but he tones it down when at work. When it gets cold, he just layers on more hoodies until it gets really cold, at which point he busts out the big, fluffy jackets. He's a vegetarian and, though he likes the look of leather, he obviously won't wear it. He likes scarves, though, so those are a common accessory in the colder months - and in summer, when he's flying. He wears a flying scarf and aviator goggles in the squirrel-a-gig, even though it has a closed-in cockpit, because reasons. (Also, though those are obviously made of leather in real life, Dean's are not.)
Dean never wears underwear, though he doesn't usually sleep naked. He has a big collection of pajama bottoms, which he wears almost exclusively with plain white tee shirts. Lately, he's developed a fondness for wearing kilts, so he may look into getting some when he gets back to the present. Also, he has a new accessory: Gale gave him a handkerchief that changes colors between gray, scarlet, and yellow when you flick it. He wears it tied around his wrist and usually leaves it gray.
Because his tail is high enough, he can wear it above his pants without them riding scandalously low (and the tail covers any embarrassing plumber's crack when he squats or sits down).