Well, the wings have always been something I've tried to wrap my head around but as for pants it isn't that hard to visualize. Sure, it would be difficult at first if you weren't used to wearing pants/used to having a tail but the one limb at a time rule would still apply.

Actually I got a YCH in the past and the way the artist designed my bra in it, while not without flaws, actually works out: http://www.furaffinity.net/view/14975152/

Granted my frill is still a bit of an obstacle to wear things comfortably. ^^;

The pants and tail thing I can definitely understand. Probably some kind of strap like a belt that goes over the tail or maybe room for the tail to pop through. Though in dragons the tail hole is at the base of the tail so I guess more fabric like a sock for the tail could work. Come to think of it. Tails are skinny and vulnerable to the cold more than the rest of a dragon, where are our comfy knitted tail warmers?

As for shirts and coats, maybe have the outfit slip over the head with special slits that secure under the wing membrane with zippers or buttons or snaps, its a bit of work to figure out but I'm sure that if the civilization were to exist, and if the civilization evolved to care enough about their bodies to wear human like clothing, then maybe it would be developed by some kind of textile engineer,

Easier to figure out a feral dragon, cape or robe or pancho like thing with a hole for the head and your done

lol if thats the case then I just imagine one of those car or boat winterizing covers you see. But dragon shaped.

or those things you put on horses?

that also works

Well we're just guessing because we only have our own clothing. In a hypothetical world where dragons or other anthropomorphic animals existed they would probably develop their own clothing shaped around their bodies.

In the end most of the clothed dragons around FA are less about what they could wear and more about what the person who created them would wear; for example all those loincloth dragons are mostly for visual appeal.

http://www.furaffinity.net/view/7780606/

http://www.furaffinity.net/view/7780631/

 ADF did something thinking about how it could work out, go look up on his gallery ^.=.^

Oh wow, I forgot he did these actually.