Is there a whole class of clothing which you detest wearing, but which you find it hard to avoid?
Find an alternative.
For me, it's pantyhose. They don't breathe, the tan color looks weird to me, and I hate hate hate the way the waistband slips down. For years I didn't like wearing dresses or skirts to business or formal events because of the expectation of having to endure pantyhose. Now, when I decide to give up my pinstripe slacks for something a little more girly, I wear stockings or stocking-top hose in other colors & patterns .
What about you? What piece of clothing do you loathe and how do you get around it?