A lot of incidents of crossdressing in order to reach a secondary goal are also not permanent lifestyle choices. I remember a story about a girl that did so to serve in the civil war and then went back to dresses after and went west to find a husband lmao. Such things were disguises for other means and likely not even desirable for the individual aesthetically, like many people view fashion today.
Until relatively recently in history, "fashion" as a purely aesthetic pursuit was really only for a small subset of the well to do. For everyone else it was entirely utilitarian, dictated by class, means, and often your role/job. Even a lot of the nobility of yesteryear likely scoffed at dandies/fashionistas for being gaudy and flippant about spending on clothing. The idea that fashion and clothing are personal expressions of your individuality and must be expressed for utmost happiness is marketing for an industry. It's no more silly to think you have to dress a certain way than it is to think you have to drive a certain car or have the "right" phone in order to be fulfilled.