Definitions lie in both the eye of the beholder and the mind of the beheld. To one, wearing a bra for gynecomastia is crossdressing while most here would starkly refute that. To another, upon viewing someone AMAB in a dress, might consider that person as crossdressing but the person in the dress is presenting themselves as they see themselves. At the root of the word, it's not problematic, but the word carries strong social stigmas.
Per the simplest definition (socially identified male wears clothing socially assigned to the female population), I have crossdressed. I have worn clothing marketed to women and undergarments designed for women (though I have breasts). Do I consider myself a crossdresser? Outside the base definition, I do not. However, society will perceive me ultimately as they do. Do I care if they considered me, on my trip to the coffee shop in leggings and a t-shirt with strap adjusters likely noticeable, as a crossdresser? Ultimately, no. Did anyone? I cannot say.