Interesting thread mostly because to me, it has always seemed that men get off easily, wardrobe wise. The same suit jacket will be in style and look great for...decades and can be freshened up by changing out shirt and tie. Or if you're more the jeans/shirt kind of guy--in my experience, most men wear very similar shirts for...decades, if not the very same shirt. Until the past maybe 5-10 years, my biggest problem was trying to convince my husband he needed to retire some very threadbare shirts---especially when he wanted to replace the 10+ year old shirt with an exact replica....
BUT somehow, that's changed and he is much more likely to wear different colors, different patterns, different types of shirts. Still mostly docker style pants, of various neutral colors and shorts in warm weather. Last year when he worked mostly from home, I don't think I saw him in anything other than sweats for....months.
I think women have it rougher. If we do not change (somewhat) with trends, we risk looking frumpy and old. If we try to follow trends too closely, we look silly and old. I have now reached the stage of my life where I need to always stick with 'classic' and to aim for 'elegant' which is mostly a miss, and to throw in an occasional fashionable piece such as a ruana, which is fabulously one size fits all and I loved it....until my son asked if I was giving up and wearing shaws now....