Shoes with work dresses

[AllProperTeaIsTheft]

I'm early 50s and a teacher. I've been wearing more dresses lately and find it really hard to know what footwear to wear with them. My go-to would always have been knee-length boots, but that feels a bit dated (and wintry). I've tried looking at pics of a White Stuff navy jersey print midi dress I have, and similar others, and all the models are wearing trainers, which are too casual for work.

I need flat and comfortable, as I'm on my feet a lot and have a tendency to plantar fasciitis. Also, not sure whether to wear natural-coloured tights with them or what! No idea why I'm finding this so difficult! Wondering if I can get away with tan leather trainers...? I quite like chunky-ish shoes, but am not a fan of loafers, as they never seem to fit me well or be comfortable (I have high arches and my feet are narrow at the middle and heel, so they tend to gape).

Any suggestions, oh wise frequenters of S&B?

Following. This is something I struggle with as well.

Are you me Op? This is me almost exactly..not a teacher but I have a job where I an on my feet a lot and also struggle with plantar fasciitis.

Glad it's not just me! Some people seem to wear ankle boots with a midi dress, which I feel looks weird on me (but fine on models!) And fine tights with chunky shoes seem odd too, somehow. I think maybe I'm overthinking it!

I wear navy blue leather brogues with blue tights, or patent leather black brogues with black tights.

Hmm - maybe I need to go full-on blue then! I quite like the idea of tan with the blue, but then I guess it would definitely need to be natural tights. I have some kind of cream/nude, chunky sort-of-brogues. Maybe they would work with a dress and natural tights. I've only ever worn them with trousers...

Flat laced up ankle boots until the weather is warm enough for shoes. Most of my shoes are from Pretty Ballerina.

I wear plain black DM shoes with dresses and skirts.

I wear loafers with dresses. I’ve also got some flat black leather trainers, very non sporty looking which I think are a bit smarter.

I’m a teacher too and wear jersey dresses for work most days. I wear them with Chelsea style boots in autumn/winter and ballet flats in summer. I can’t wear the cheap ones with no support but really love some I’ve got from FitFlop.

I've got some Fly London chelsea boots but I've never worn them with dresses. Maybe I should!

I would say these may not be great for PF

If you can afford it, Russell and Bromley do amazing flat shoes that I find supportive and extremely comfortable. Their Charming range look good with dresses as do their slim loafers. Also lots of neutral colours

I wear wedge sandals in the summer, which are not allowed according to our dress code, but nor are the trainers or DMs that other staff wear. We get away with a lot more in our junior school, the senior school is much stricter.

I'm not sure what I'm going to wear with skirts/dresses after the holiday, my shoes suddenly seem a bit dated. I've got a pair of loafers but not sure what else.

Good to know as they don't look supportive at all. Thanks.

I've got their Opera loafers which I love though they are a little tight.

Eek - Russell & Bromley are a bit pricey for me! I have a pair of black ballet pumps with thicker soles, but I still don't find them great for work all day. I've caved and bought a new pair of brown Fly London boots, but am looking at other shoes too. Maybe some tan loafers if I can find some that work with my foot shape!