Winter dresses and boots - what style?

[Bettysbooks]

I'd like to try wearing dresses and boots (long or short) this autumn and winter instead of my usual trousers, but have no idea where to start or what styles of dress and boots work together.
Can anyone give me some ideas please? Budget - am happy to pay for decent boots which will last. I Dresses - I'm petite, mid 50s, not keen on anything too fitted (my summer dresses are Seasalt and White Stuff).
Thanks all

For dresses I'd suggest you stick with what you like but get long sleeves if available and darker colours. Seasalt and White Stuff will do winter dresses. You can wear a cotton or tencel dress in winter as long as it's not a summery colour.

Add layers underneath - a full slip and a long sleeved thermal vest /top. M&S do great ones. But get them smaller by at least one size, maybe even 2. They'll still be comfortable to wear but won't add bulk under the dress. Cardigans, fleece, jacket, whatever on top. Minimum of 40 denier opaque tights - you can get 100 denier and even higher which are fabulous in winter.

Boots - I have these. Love them both.

Lanx
Joseph Cheaney

This is one of my winter dresses. It's a very thick flanlette cotton with a lining. I wear it with the Lanx boots.
Cabbages and Roses Winter dress

This is another. It's a very thick soft cotton. I wear it with a long sleeved thermal vest underneath and a thick cardigan, again with ankle boots.

Palava Edinburgh Castle Dress

Two wonderfully different examples@NatashaDancing! (I always forget how breathtakingly pretty the Cabbages dresses are. And I’d never noticed Edinburgh Castle on the Palava dress.)

I was going to leave this on another thread (fabric mix ) but the new season Christian Wijnants boot wearing is so very fine. Also very much my style of dressing, though I’m more likely to opt for a wool / cashmere mix going into Autumn.

I would start by trying on what you already have and seeing what goes and what doesn’t.

‘Dresses and boots’ is honestly such a broad category - you could wear anything from a fitted mini dress to a slouchy knitted maxi dress with anything from chunky boots to slim heeled boots.

So maybe start with what you already have and either look at layering up (eg t shirt under a dress, or a jumper over a dress) for winter or think about getting versions of your summer dresses in more wintery fabrics or colours - you could buy a similar shape or style to what you already have and feel comfortable in.

Adding some photos of what I’d wear - very different from what PPs would wear.

I’m 56, and petite. I have two pairs of block heeled ankle boots; black and brown suede and the same in knee length. The knee length are from Clarks and v good value. I wear them with a variety of wrap dresses, tunic dresses and pinafores.

That's quite different from my 2. It's a very, strong, take no nonsense look. I like it. (Although you could still fit a thermal vest under it)

Always, @NatashaDancing! (Spoken as one who put the heating on for a few hours last night.)

This is another way I habitually wear boots in Winter.

My current favourite skirt for this sort of look is an ancient silky pleated thing from Zara! (How I miss Q&B for style inspiration, though.)

I also have a new silk/cotton mix dress that looks a bit like this (it’s not this, and not see through!) which I’m looking forward to wearing with a tweed or velvet jacket, Shetland jumpers and endless stompy boots through Winter.

I love my Lanx boots too @NatashaDancing Currently keeping a close eye on their site to see if the Dinkley in oxblood are back in my size.

Thanks for all the replies and ideas everyone. Am especially liking the Lanx boots. The Cabbage dresses are lovely too but may be too long (am 5'1").