I usually start with shoes - it doesn't matter what outfit you pick, if the shoes aren't appropriate, you'll struggle.
I'd dress the same for the pub or lunch with friends.
My basic no fail outfits are, but everyone's different, I like separates, some of my friends only wear dresses:
Leather look leggings, boots and a long hip length jumper. I've got boots in lots of colours to co-ordinate with my jumpers, black, khaki, tan, stone, grey and leopard.
Midi pleated skirt with thin roll neck, long boots and a biker jacket
Straight leg jeans in black or blue, v neck skimming T-shirt in black or white and a blazer in camel, black or navy with either loafers or boots.
I've also got a tan leather shirt dress and longer length shackets that I wear over jeans and longline cami
Knitted dress with boots and a flying jacket