Great thread. I always particularly enjoy @Floisme's musings. My two penneth worth is find a look that really suits you, and that expresses who you are and then tweak it constantly. I'm tall and broad-shouldered, angular not soft, and my colouring is all contrasts. Consequently I suit very structured clothes, and clean looks. I know I would look an absolute horror in prairie dresses, frills and flounces so have steered well clear. I do suit midi-dresses that have a waist and structure, and trapeze dresses so wear those and accessorise them to the current sensibility. I don't suit trainers with dresses so don't wear them, but have fisherman's sandals, flatforms and Chloè chain flat sandals.
I never suited skinnies so never wore them, I wore narrow-legged dark selvedge denim with a turn-up. It still looked modern, but was much better for my aesthetic.
I like heels, not every day, but they do suit my style of dress, so I wear a block heel (I've also just bought some kitten mules and lowish wedge mules, both of which look very modern).
I've always liked a centre parting, a massive quiff , slicked back hair or a giant bouffant. Soft hairstyles don't really do much for me.
Above all, fashion should be fun and expressive. If you're interested in being more modern, just be considered about what you wear, I'm constantly thinking about outfits and trawling websites.
Who says what's modern anyway? The people I see out and about that look great very much have a personal style rather than an up-to-the-minute look.