S&B Are You Up for a Challenge? Style Me!

[GrimDamnFanjo]

Help!
I need to finally find my style and build a new wardrobe [not literally!]
I seem to have lost my way and now at 48 I really want to start putting together some key looks to take me through the next decade or so.
But I do have a few challenges...

1. I work from home with my own business. So I don't need a work wardrobe - but I do want to be vaguely presentable. And to put some clothes on which I find fun, exciting, but comfortable.
2. I'm a size 18, 5'3" apple shaped, big boobs [but have lost 3 stones since March and intend to carry on and lose the rest of my weight.
3. I look younger than 48 with deathly pale skin, blue eyes & [dyed] copper hair. I'm a Clear Winter.
4. I prefer dresses to trousers [but like leggings/jeggings] but never wear skirts. I'm not a breton top, skinny jeans gal.
5. I like coats, wrap dresses, my supergas, handbags, unusual jewellery, 40s vintage looks [often pin curl my hair]

In my head I want to rock a quirky eclectic style during the day time - evening is much easier. I'm happy to buy second hand via Ebay.

Help me! I'm open to everyday outfit ideas, brands/shop recommendations. I think if I can just get some inspiration that would help a lot - I don't trust my own judgement to be honest!

I would go down the Lagenlook route but with quality expensive jersey bits. That tends to suit apples and the clothes still fit as you lose weight. Add accessories to give it your own retro-quirk.

Lagenlook dresses look good layered up with leggings and tops which is good if you sit around a lot as it gets colder working from home.

I would avoid the ‘Made in Italy’ stuff and go more Masai, Cabbages and Roses and Oska etc

THESE tulip shapes are a good foundation. They are flattering, keep their shape,look quirky and stretchy so don’t feel restrictive.

The styling on the Masai site can’t be off putting but there are gems on there.

THIS sort of look.....

Funnily enough I'd been quite taken by Lagenlook! I was worried that it may look a bit drowned though?

The Masai stuff is less pouffy and just on the right side of flattering to my mind.

Some of it is ridiculously oversized though and not flattering as a consequence. I think if you have something fitted underneath or some part of it is fitted then it works better.

How does including fitted clothing work?
[this is the bit I struggle with!]

If it is sleeveless then wear something clingy underneath or go for a design where it is fitted under the bust/arms otherwise it can look like it’s drowning you to my mind.