Thanks Bonsoir, I'll check out those socks and trews.
On the subject of the OP, I second the haircut. Haircut and nice shoes and the rest in between follows ... sort of.
Makeup doesn't need to be made-up looking. Tinted foundation, filled in brows, concealer, blush (Bobbi Brown do cream blushes that double as lipstain)), 'tightlined' eyeliner and a boggo mascara and a 'your-lips-but-better' lipstick (can recommend Lipstick Queen Saint) will make you look groomed, younger and more glowing, but not clownish.
Other things to consider.
Dresses. I love them as I'm on the short side and they make you look finished and longer. Get the length right, though, knee, just above the knee is good. Calf length can sometimes look frumpy.
Decent trousers. I like either thin fit (60s style, not the modern skinny so much, doesn't suit me) or palazzo in a heavy crepe. I think Banana Republic do a range of trousers in different styles.
Decent outerwear, cashmere cardigan (uniqlo is cheap but eBay good, trench. Thin gauge T-shirts in off whites/greys/oatmeals.
I also mix all this up with lots of vintage - YSL silk shirts, I love vintage pattern sweaters, vintage hermes scarves (those are not cheap but you can pick up old silk scarves for peanuts)
Shoes. Boots, flats and one pair of walkable-in mid height heels with a not-too-thin heel (they just fall in cracks and scrape up)
Consider going for a few weeks to various shops you like the styling of -- for example Whistles, or APC, or Issa (I'm a nutter for dresses) whatever. Get a sense of the sizing. Whistles, for example, is super generous.
Then get busy on eBay. I buy loads on eBay and sell the mistakes on (I either tend to buy high end as the resell is easier but also hunt out the 99p shit)
Good luck