Wardrobe intervention needed please

[MarianneFaithful]

Please could I have some suggestions for a winter wardrobe. I am neither stylish nor beautiful.
I'm late 40s, tall, inverted triangle, slightly overweight. I need casual clothes, but have a tendency towards scruffiness, which I'm trying to avoid. I have clothes for autumn, which I'm happy with, but don't really know what to wear when it gets colder.
I have trainers and flat black knee-high boots. I have winter coats. I used to wear skinny jeans but they really don't suit me. I've bought some boot cut jeans, but I feel like a throwback to the 90s in them. I prefer trousers to skirts
Following a pretty rubbish year (ill-health, divorce) I need to feel better about myself so please could I have some suggestions.

No idea, my head is full of summer :)
But you need to start feeling better! Go to a makeup counter and get a pick me up, get to boots and start a new regime, do your hair nicely…
I imagine coats are the way to go? Beautiful warm wool coat in a colour? A thermal raincoat (rains are gorgeous), boots.
Jeans are tricky, I love wide legged, but guess not the easiest in winter. What about barrel leg? They are flattering
Have fun pampering x

Think what your favourite clothes are and more of those

Look on me+em for inspiration.

I tend towards scruffiness. I’ve realised that very casual clothes don’t suit me, eg sweatshirts, baggy things, trainers. Other people can look effortless chic/stylish/trendyq. I can wear trainers but they have to have some kind of elevated feature or be very smart. I have noticed the whole world now wears mainly trainers but that doesn’t mean I have to. Same applies to clothes, if you feel you look a bit scruffy look for elements of elevation, eg instead of a T-shirt a sharper shirt or blouse. Darker denim is smarter than pale. I’m also an extreme inverted triangle and dislike skirts, it’s a difficult figure to dress, you could try a House of Colour style day.

I'm sorry to hear you've had a tough year & it's great that you're now looking after yourself. I hope you'll feel a lot better for it.

I think I'd start with the outerwear as that's what you'll see most of when you're out & about in winter. A nice coat in a shape/fabric/ length that suits you. And a scarf & hat (if you wear hats)
Then good foot wear- I'd look at modern Chelsea boots or laced up ankle boots. Pretty much everywhere is doing them but I'd look on sites like whistles / jigsaw/ sezane/ ME+EM for inspiration & to see how things are styled & when you see something that catches your eye & you can imagine yourself wearing then you can shop around for similar at the price you're happy to pay

Maybe consider colours other than black for leather boots - I'm always drawn to rich colours like maroon or plum or chocolate or bottle green etc

A good quality bag is next to think about then once you know your coat & footwear. I favour soft leather minimalist with no logos but again browse online till you see what catches your eye

After that I think bottom half is next. At the moment I am buying Ponte/ structured jersey material tailored trousers for work from places like whistles. I'm tall & I'm enjoying either cropped wide legs which I wear with laced up ankle boots (I have the whistles Asha boots) or tapered ankle length
Jeans wise I'm wearing either straight leg with a turn up or barrel leg.
I tend towards apple shape & I find the straight leg balances me out far better than skinnies ever did.

Get your hair cut into a new style & experiment a bit with makeup / perfume

Of course I know you can't do all of these things at once but I love having a plan & a focus to things so this is how I would approach things

Thanks for all your suggestions and good wishes.
I'm happy with skincare and I've had my hair restyled, so that's all in hand.
I'm still a bit confused by clothes. For example, in autumn, I'm wearing trainers, rolled up straight jeans, oversized shirt. Or cropped combats and a smart t-shirt. How do I change that when I don't want bare ankles? I really struggle with shoes and definitely only wear flats now. I love my tall flat boots, but what do I wear with them? What about a thigh length jumper, leggings & tall boots? How does that sound? What else?

I can't buy shoes from mainstream shops. It's pretty much men's trainers or Duo (which is very £££).

And I have all the nice bags I could ever need.

@TheCategoryIs, would you mind sharing any recent outfits that you feel good in? We sound quite similar.

@MarianneFaithful Well you could never describe me as tall, my legs are ridiculously short, which only makes the triangle worse.

As I go through my forties, I feel my best looks are those which are very neat and simple, so a fine knit jumper or cardigan and straight or skinny jeans and ankle boots. The sort of outfit that can take you pretty much anywhere (apart from a club, wedding or black tie event). In the right colours and not necessarily the cheapest versions I could find. When I was younger I used to wear more colours together, and worry if I had too many clothes the same colour, but now I think it looks quite stylish to wear say a navy T-shirt with navy jeans and don’t worry if I often look like I’m wearing very similar outfits. I add interest with accessories but again quite understated.

The bare ankles thing is easy to fix. Socks. Lovely socks in interesting colours, patterns or fabrics. Men's are often best.