If I had to put together a list of Crimes By Fashion (as opposed to Crimes Of Fashion), the necktie would be in #1 place by a long way -- but a lot of other items of male formal attire would be there too. Dress shoes, for example, based on a style that seems to have become frozen around 1900 and makes no concession towards such necessities as being able to walk across a slippery pavement, never mind comfort.

Women's clothing probably has more scope for creative discomfort, but is also more varied. So I'll leave that subject to someone else.