Oh goodness, yes, the blue and white check - that one was frightening. And his 'wino who lives in a dumpster' jacket in Loyalty. Some of his clothes were definitely a cry for help. (I was so excited the first time I saw Loyalty and Wesley's in the hospital with Angel, thinking 'ah hah, there are all these trained medical professionals around, they are bound to see that this man is having a nervous breakdown'. And then I realised that as he appeared to be co-parenting a baby with the disgustingly healthy-looking guy they would just assume that he was the one who'd been stuck with doing the nightfeeds...) He clearly goes through a period of very bad clothes decision while mid-breakdown and then snaps out of it once he's into the truly dark self-loathing and bitterness place.

Wesley must be the only guy in the world who coped with PTSD by becoming even more unfeasibly hot and suddenly learning how to dress well and be amazingly good in bed.