I'm 41, I've always been pretty happy with my looks and my body, though I've never been conventionally attractive or had a perfectly proportioned bod (though basically slim). I've always dressed in an fairly unconventional way, with a lot of colour and patterns and am too lazy to be 'chic'. I admire the look on other people, but IMO unless you are very 'polished' with simple, classic clothes, it you just look a bit anonymous and dull rather than sophisticated.
I was always makeup free except for going out (and then it was usually weird clubby/gothy makeup), but started wearing normal makeup to work when I was about 38 because I'm in a smart-dress office and I just decided that I'd got to an age where smart clothes and no makeup just made me look a bit severe and like I didn't care about myself enough to make an effort. I mean, I still only take about 2 minutes to put a face on, never been able to do eyeliner, and fuck contouring or anything like that.
In my late 30s I started looking at certain things (like that trend for leggings and super short denim shorts a few years back) and thinking it was cute but it's really a look for The Kids. I don't subscribe too much to any 'dressing your age' shit though, I still have short dresses and wear big boots and stuff.
My overall look has been toned down by 6 years of working in a smart office rather than ageing because I have to own stuff I can wear to work, and also I don't go out partying as much so there's no need for wackier stuff that I would previously have mixed into my casual wardrobe.
I do feel a bit sad that, now and then, I dress in more my 'old' punkier way at the weekend and I feel I look a bit like I'm dressing up! But overall I'm cool with ageing - I have my husband, I have my kids, I genuinely feel no need for other people to find me attractive, and I'm finding getting a bit older interesting and quite exciting. Aside from the chin hairs!!! 