I agree with Temptress that it's about finding your own consistent style, including hair and makeup. Temptress sounds like she has an amazing commitment to beautiful clothing, but dressing well doesn't have to mean such a high-level investment!
I have a very pared-back style and dress in variations of the same outfit every day. This might sound boring but actually it just look really well-put together, it means my whole wardrobe works together and people get the sense that I have a recognisable style.
My wardrobe is the opposite of Temptress's. I have six pairs of trousers, a handful of shirts/blouses, a handful of t-shirts, three great jackets, three great coats, three beautiful cardigans, two skirts (a midi and a maxi), three dresses (two smart casual and one glamorous) and some sweaters/knits. For the weekends I have a couple of pairs of jeans and shorts and some sweats. Not sure how many pairs of shoes but definitely less than a dozen. I also have a few scarves, a couple of good bags and some very strong pieces of jewellery.
Everything fits within a restricted colour palette of black, cream (I don't suit white), mustard/old gold, navy, pale grey, and olive. And everything is top quality, both in fabrics (linen, cashmere, high-quality wool) and cut. Because I really only buy a couple of items a year, I can afford to spend a lot on them. If I find a shape or style that I really like, I will often buy two or three in different colours.
I wasn't born with this, I evolved my style over years and only became really confident in it in my mid-30s. Making 'mood boards' by collecting images of what you like and looking for consistent items helps you identify good base pieces that you can build around.