I had a year, my senior year in high school '91-'92 that I looked my best. It was a very preppy time, and I fit the mold. I had great hair, I was at my ideal weight, I just looked good.
It's been all down hill from there...
I guess that you could call my current style fairly preppy. I go for good quality over obvious name brands. I tend to only wear sneakers when at work because I'm on my feet all day. Otherwise leather shoes. In the summer I wear my Birkenstocks pretty much all the time when not working. I discovered them when I first started dealing with plantar fasciitis, they are incredibly comfortable! And no I don't wear them with socks, I've been gifted with very attractive feet for a man!
Shrek says I still look like I did when he met me...I think he's crazy but, I did look good around then. And I still wear flannel shirts, t-shirts, tank tops and jeans. Tops and dress pants if I have to look nice or dress professionally. I've always worn flat shoes, even in high school.
If it fits and I like it I wear it. I don't care what is in fashion and what isn't.
I figure if people don't like the way I dress they don't have to look !
My favorite ensemble would be blue jeans and a t-shirt and no shoes.
I don't dress up often but when I do I scare the dogs LOL They have no clue who that woman is coming down the stairs .. after a quick sniff they say it smells like Mom but it sure doesn't look like her.
I loved bell bottoms when they were in style but really can't think of any other fashion fad right now that tripped my trigger.