What to Wear
Choosing clothes for your anthropomorphic character is perhaps one of the oddest choices you're going to make. Society's rules of modesty don't apply. In the first place, anthro characters are seldom drawn anatomically correct. Furthermore, many of the body parts that would usually be covered by clothing are now covered in fur, feathers, or scales.
The costuming decisions you'll make — if any — will be primarily based on projecting a personality for the character. This explains the plethora of furry characters that wear only half of a standard outfit — shirts and no pants, for example. Generally speaking, anthro characters tend to have just enough clothing to project a personality trait, and not a single thread more.
If you're using clothing to indicate the gender of an anthropomorphic character, try to avoid some of the visual clichés. Too often, a bow is placed atop a character's head as a sign of her femininity. Likewise, neckties — usually tied around shirtless collars — have become overdone. Find some other ways to express gender.
Of course, there are no hard-and-fast rules here. But it can be observed that the level of clothing on a furry character rises and falls with the number of human traits bestowed on the character. The more a character walks, talks, and acts like a human, the greater the tendency to wear at least some clothing. The more a character identifies with its animal side (Snoopy, Garfield, and Calvin's friend Hobbes, to name a few), the less apt it is to wear clothing.
