What size are you what's your hair colour and what clothes do you like?
Personally...
For winter, I like a grey wool coat (had mine from ebay and charity shops, lucky finds. Tk maxx if u want a goodish one for around £40. Black jeans. Seasalt have some with side buttons and high ish waisted so good for tummies (like mine..) they are £60 but I think the price per wear will make them worth it. Also I'll get maybe a skinnier fit in black or grey.
A good scarf (grey) maybe primark if u don't want to spend.i had mine from toast ages ago.... Most expensive thing I've every bought. Lasted well and I love it. Bought it before babies when I had money!
And a selection of vests, long Sleeved tops in whatever colour. Save on these.
Also a slouchy grey or black or navy jumper.
Feet. I wear doctor martens. Have forever. Shoes or boots. Apparently they are 'in' this season so can prob get a knockoff pair from new look, or places like that. M and s have some.
I've got a charcoal pinafore dress (these were in shops everywhere recently so maybe in sale?) and will wear this with long or short Sleeved tshirts coming up. Also with thick tights and I want to get some of those thick rubbed grey socks. I don't know if anywhere will have them yet. Maybe a mens section somewhere 
Anyway, this is what I'll pretty much be wearing. I have a child under 3 too. I love summer but find winter so much easier to dress. Hth?