This wins the award for best thread title! I haven't seen any glaring things with my current T (male), but he usually dresses himself fairly well with standard business casual clothes (slacks, button up collared shirt, polo shirt, solid colored sweater, etc). Usually he matches colors well, too. But last summer, he wore this crazy printed short sleeve button up shirt with khaki slacks. The shirt was a cream color and was printed with palm trees. It was just so different from what he usually wore, so I seriously wondered how he could think it was an attractive choice. I chalked it up to him being single, but now he's married so hopefully his wife will help prevent future fashion faux pas.

On another note, the sexiest thing he's ever worn was just recently when he wore a perfectly tailored dark grey slacks and a fitted black v-neck sweater with white collared shirt underneath. He works out and is very fit and toned. I never really saw him as 'sexy' until that day. I keep hoping he'll wear it again.