39, lost way, boring, what to wear with these boots

[CluelessDresser]

I'm 39, not into fashion really, I'd say dull but I try to look presentable! My usual attire is quite countrified (I'm horsey) - sports leggings or jeans, boots, jumper and a waterproof coat, gilet or down jacket. I do have an occasional foray into trying to look nice for the occasional time I go into town or the about twice a year that I go out with my DH for dinner.

I just bought these boots (pic below) and realised I have nothing to wear them with unless it's skinny jeans and a jumper, I'd like to wear them with a casual dress and tights, is this fashionable?

I do have a couple of "winter" casual, mid thigh length, plain coloured skater type dresses in my wardrobe but I haven't really worn them for years and I don't know if they're still in style. I'll post a pic, they do look nice on and suit my shape (skinny pear!?)

IMHO, they are too clumpy for that style of dress.

Here are some short dresses - you can see the styles and colours and textures that are currently fashionable, and how they’re being worn.

https://www.zara.com/uk/en/woman-dresses-mini-l1083.html?v1=2290794

I like the boots to go with that dress, I have a few dresses similar and wear them with DM boots

I had a look for an updated (and more sophisticated) version of your dress and found this. Possibly more than you’d want to spend but lovely fabric and a very elegant cut. It would last for ages. But I wouldn’t wear it with those boots.

https://www.cos.com/en_gbp/women/womenswear/dresses/product.v-neck-double-faced-wool-dress-blue.1139208001.html

I think your boots would look fine with a sweater dress or a short cord pinafore but they’re not going to enhance anything dressier or more formal.

A few more examples of dresses currently being sold by & Other Stories, Cos, Massimo Dutti.

That's actually very nice, although yes a bit pricey, thank you.

I would struggle with a jumper dress because of my shape, although I have seen some that look great, I definitely suit a more A-line shape (I have a long body, bottom half bigger than top, tiny boobs) so anything remotely clingy or body con just looks stupid.

I'm a fan of a clumpy boots look! I live in a small, rural ish town a long way from any big cities and people don't tend to dress smartly.

God I'm clueless!

Nothing wrong with clumpy boots! Most people love them.

Yours do seem to be quite a dull colour (perhaps it’s the photo) - so might look best with a longer, brighter dress, rather than the one you’ve shown.

And short dresses do look a bit more fresh with knee high boots this year. (Just browse some websites to see how they’re showing the clothes.) But no one’s obliged to follow this fashion.

I would happily wear that outfit and I’m a reasonably fashion conscious city dweller. I do love a chunky boot and dark clothing though.

Have you ever had your colours done? It made a big difference to what I wear. It’s not even about making big changes, more about how you can tweak your current look. There’s a lady on insta called Style Me Happy who does it for £35. She sent a long report through and I was very impressed.

I disagree. I think they are the right amount of clump.

Thank you, I will look her up, it's not something I've ever heard of!!

See I don't think any of those 4 dresses pictured above would suit my shape!!

Love those boots!

How about thick wooly leggings or tights, mini skirt and oversized jumper? E.g. mini leather skirt (black) and oversized mohair or chenille jumper in cream/beige

I love the M&S leather leggings with a chunky knit jumper with these boots! Or a long sleeved midi dress & leather jacket