i always think women who worry about clothes being dated smack of middle aged insecurity. It's the adoption of what suits you and what you love that makes something current, imo.
Unless what you wear is tired and unloved, dated is a state of mind. A giant F YOU! to capitalist trend cycles is relevant here, and a mindful approach towards not creating waste.
And to my knowledge,. Fly were always niche. and niche doesn't go in or out of style. Many people hate them, so they will tell you they are dated. It's the mumsnet favourite put down isnt it? Who even thinks like this in real life, lol?
It's all about the terror of mortality, like social climbing, in a way. You know, how people on here are often afraid of buying the wrong kind of scented candle, in case they are perceived as working class. When in reality, if we work for a living and have a mortgage, we are ALL definitely working class economically, no matter how many Le Creuset crock pots we own or how often we go to the opera.
Someone will tell you, no doubt, that Fly boots are dated, which loosely translates to 'lower class' on here.
You need to content yourself with the knowledge that being free from concerns about adding to landfill and class insecurity are wonderfully progressive and fucking liberating!