Where the hell do I start? Complete overhaul needed!

[SunChaser]

Every single day of my life I wear:

Really cheap bootcut jeans.
A cheap jumper.
Converse.

Where does one even begin to be stylish? Am I a lost cause?

Figure is an acceptable, albeit unremarkable size 12. Height 5'6''.

Any help gratefully accepted!

You sound like me!

Watching with interest (while dressed in cheap ill-fitting bootcut jeans, cheap (Tesco) jumper bought between children while of indeterminate size and spotty socks bought for me by my MIL. Sigh)

Been there, done that... I was overweight too. I started by loosing weight so you are already ahead of the game

Then this is what I did:
Got a haircut.
Got some nice tops and jackets/coats etc. and ear rings.
Didn't break the bank - just a few tops from tk maxx (sale area) and some coats/jackets from the charity shops, earrings from a shop selling cheap stuff but pretty. Got some jeans from m&s

Next, I need to get a makeup routine (very quick, maybe just mascara and lipstick)

And I need to make sure my wardrobe doesn't get stale again. So a new top/jeans/skirt every month. I have made friends with my local charity shops again...

Not that I am particularly stylish - but I have some clothes to choose from when I am standing in front of the wardrobe. And am happier with the way I look

in order
great haircut
eyebrows done
get people at various beauty counters (bobbi brown, mac, benefit) to do your makeup and choose a couple of nice bits
get a great coat
and a pair of really good jeans that flatter
work from there

Agree with mazzystartled, but would insert "get teeth sorted" in between hair and eyebrows, and "get nails sorted" after that.

All the above,
There are loads of knitted dresses/ tunic tops that look great over thick tights or skinny jeans at the mo. That should be within you comfort zone and is a nice way to get a wee bit more dressy.
So I'd start with finding some good skinny jeans- don't worry about the brand- just go somewhere with a lot of choice, try loads on until you get the right ones.
Get a couple of pairs of thick tights (one black and one coloured- eg plum)
Find some knitted dress/ tunicy things. Uniqlo has an ever-evolving selection that won't break the bank. Then go from there.

It sounds like you already have your style, but you're obviously bored of it.
How about exchanging the converse for a nice pair of boots. preferably a pair that can either be worn under your bootlegs, over a new pair of skinny jeans or beneath a skirt with a nice pair of tights how about these.

Eyebrows, hair, makeup.
Jeans that really fit and flatter.
Footwear with a heel.
Work on your posture.
Nice perfume.

Forgot most important bit:
A great bra that fits (get fitted by a professional.)

go to peakocks and buy something colourful.