While many would like to deny or ignore the fact, appearance is a primary way humans communicate with one another (1 Sam 16:7). Fashion is a fast-changing dialect. The problem with being stuck in a time-warp is that, although you may be comfortable and perfectly happy, many of the people you meet no longer speak “1985”. Nevertheless, I know several women who still wear their clothes from high school but do not look dated. How? Their style is timeless.
Understand, I am not advocating timeless, or traditional as I normally refer to it, as the only way to avoid misunderstanding. Contemporary works, as well. My point is, and it has happened to me, your appearance may not be accurately reflecting who you are on the inside. Especially if people don’t understand what you are saying.