I don't see the flat shoes as a major problem. Look at some of the upmarket advertising for comfortable shoes - they have obviously chosen attractive models and dressed them nicely and you don't even notice the shoes. I would definitely give toe rings and ankle chains a miss as being just tacky.
Dressing in a monochrome cream palette can look very glamorous though unfortunately I am so pale as to look corpse-like. I look much better in a navy blue or black monochrome look. Things that look glamorous are a limited colour palette - two or three colours at the most. Some garments are just more glamorous than others - an anorak versus a beautifully cut and dramatic longer length coat or a cardigan versus a jacket. (Almost nobody can make a cardigan look glamorous and as for one of those long droopy cardigans that end at your widest point, I just ask myself why.) Think silk, satin, good quality fake fur or the real thing. It takes youth and good genes, to make linen look other than a creased mess. On the other hand, I think there is a black or brown leather jacket for everybody. I am fairly sure though that there is not a white shirt for everybody - I know it's a wardrobe basic but they just don't suit me though at a pinch they are passable with a black suit.
A good tailor who does alterations can make ready to wear look like couture. They can suggest things to make a garment flatter that I would never have realised needed to be done. The cost of alterations is a good investment (but never buy something where you need to do something with the shoulders as this is the hardest thing to alter).
I personally like pearls - not graduated and a decent size - for dressed up outfits because they add a lot of light to your face. You can do the same with other jewellery if that's not your thing. Or pearl earrings? Simple symmetrical jewellery in real gold or silver is best.
Do not clutch an old handbag. Update with something modern and structured that does not look like you have or could have your lunch stowed in there.
I am now blonde and have dyed my hair for nearly 40 years. It is not brittle or dry and people are actually puzzled why I don't have blonde children. The secret is professional colour and NEVER combing through or doing all the hair - just the roots and the odd deep conditioning treatment. A visit to a dermatologist can do wonders in removing skin tags, keratoses and who knows what else. I finally have the beautiful well cared for porcelain skin that was out of reach in my acned impoverished teenage days. A dermatologist is cheap compared to all the useless face creams beauty therapists or department stores will try to sell you and what dermatologists prescribe actually gives results.
If you have a hairy face, then if you can see it so can others. If that is not your desired image, get electrolysis or laser removal.
Try to work out whether you have warm or cool undertones in your skin. Most foundation falls into those two schools. I am a blue eyed, light skinned Celt and I look peculiarly orange in anything with warm undertones regardless of how light the shade is. This carries through to clothes. Try to be realistic about this - if you're a redhead you're going to look beautiful in chartreuse and not so much in powder blue.