There is a balance to be struck. Comfortable clothes are comfortable, natch, but dressing fancy has its place. Of course, properly fitted fancy clothes shouldn't be horribly uncomfortable; comfort is the trade-off our society has made with off-the-rack clothing.
Just take the difference in women's shapewear. Most women nowadays will wear something like Spanx to keep things tucked away. Spanx are the most horrible, uncomfortable, godsawful things I've ever had the misfortune to put on my body. I can't wear them for more than an hour or two before I start feeling slightly nauseous.
However, a well-made corset that's sized to me specifically? Don't let the popular notion of corsets fool you - those things are infinitely more comfortable than "modern" shapewear. I can wear one all day without any trouble or breathing difficulties, and I have asthma. Granted, I don't tightlace, but the waist reduction is still nice. But it doesn't squish me in all over, it just moves the layers of fluff around to give me a more pleasing shape.