Winter wardrobe advice please - fashion dyspraxic here!

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I have no fashion sense whatsoever and a whole load of clothes in my wardrobe which don't fit and/or if I keep for another 2 years will probably come back into fashion again!
I have spent the last 7 years looking like the opposite of an alpha mummy and would just like to look acceptable in public.
Needless to say I have a limited budget but I need to have some clothes to wear so am prepared to spend some money.
I am scared of going into shops as I feel overwhelmed at all the choice and feel so frumpy I can't bear to look round for long, so online shopping would be good, but I am happy to brave the cheap shops like Primark if I have guidance!
I really need everything as none of my existing clothes really fit at all well, I have come to terms with the fact I am a large size 14 rather than the 10/12 I used to be. If i wait to lose the weight I'll freeze to death this winter!
TIA all advice gratefully received.

A basic list of essentials would help i.e. jeans and er....um....
that's my problem I don't know what to wear with them!

ok
what height?
do you mean a 16?
what is your basic style?
what are your priorities?
colours you love?
basic body shape?
norkage?

Once youve answered above questions I can be more specific but heres my winter essentials -

black boots (i had slouch ones and they got too worn so now i have one pair of ugg style ones and one pair of longer leather looking ones, but one pair would do)

Good fitting jeans (can wear then normally or rolled up a bit with boots under)

A chunky long cardi, I have a black one.

Denim skirt

Lots of plain tops, I tend to buy black but any colour that fits with your wardrobe. (Primark do them for aboyt £3, if I find a style I like I buy a few)

Scarfs - I have a pink one and a black one. The kind you keep on indoors I mean, crinkly ones - do you know what I mean?

So you can do -

jeans, top, cardi

same but jeans rolled up

skirt, boots, top

Then mix and match in the scarves depending on colouring of top etc.

Sorry - couldn't get to computer this week as DH has monopolised it!!
Thanks for the replies.
Answers :
Height : 5ft 5
Size : 14 but depends on the shop can be on the tight side, 16 a bit too big.
Basic style : that's my problem I have no idea...I wear jeans and tops, normally the same ones till they're mucky. I guess I'd likle to have a style, perhaps a bit more feminine, not too height of fashion otherwise I'll feel conspicuous, probably classic without being too frumpy. I'll be 40 next year.
Priorities : erm..I guess easy to wash, low maintenence and little time, always rushing in the morning so end up grabbing nearest clothes. Work from home so same clothes all the time, go out very casually so a bit to dress up but nothing formal.
Colours : pale pink, black and I look good in turquiose blue as DH always comments on my eyes if I wear that colour although rarely find the right things to go with it.
Basic body shape : average I suppose - before DD1 I was an absolutely classic standard size 12 all over- notmuch of a waist these days and bigger hips and norks - actually would say they have all blended into one Legs alright I suppose but not very long.
Norks : 36C/D.
Thanks , just answering these questions has helped me think.
Like Denim skirt and boots idea...any suggestions as to where to get them ...and shape?