Oh god should not have posted The List 
First things first: the golden rule is Wear What You Feel Confident In.
Also, I would never diss anyone for choosing to be comfortable/practical over being “in the fashion” so you do you!
Re the list: I have had a number of jobs here and there doing an odd range of stuff, and some of these jobs amounted to selling “feminine stuff”. Clothes, cosmetics, all that.
I worked mostly in brands that tacked to the 40 plus market. As a result we got visited All. The. Time. by ladies who were 50 plus how they could “look younger” and a lot of them were pretty upset about it.
These were NOT old ladies by any stretch of the imagination but most of them were now complaining they looked like their mums.
The List is basically a compilation of things we would (very sensitively I want to add!) suggest to those ladies to give their look a wee lift.
It wasn’t about looking older. It was about not looking modern. There is a difference between not being bang up to date in “the fashion” and looking outmoded or old fashioned. Most of these ladies just hadn’t made the wee tweaks to their look (and I mean wee; stuff like colour palette, trouser length) that would keep their look modern and in style without drastically changing their tastes/appearance.
Old is a state of presentation, not an age. The reason the screwed up face is first on the list is that everyone looks miserable and old with their face screwed up! Luckily this fix is also free 
I would also really really suggest a bra fitting. A lot of ladies think they are really piling on the weight as they older, but in reality because their bust is dangling, their waist looks thicker and their clothes sit all wrong. A good well supporting bra (and no, I don’t mean you have to haul them up to your nose!) will improve the way you carry yourself and the fit of all your clothes. So worth it.
I also forgot something. Brows. Brows thin and lighten as you get older. Many many ladies continue to get great stuff done with their hair but don’t go anywhere near a brow place. A proper shaping and a tint to help them look thicker makes an INCREDIBLE difference from about 25 onwards. Should be less than twenty quid about once every four to six weeks. Will lift your whole face and help your makeup sit and look better.