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What shoes to wear with these style of dresses?

7 replies

Cloudninelau · 12/02/2026 10:20

I usually wear this style of dress for work and I’m looking for some new shoes to pair with them. I’m 44, 5ft 6in, and a size 14. I find it tricky to choose shoes that work well both with tights and without. I’d really appreciate your help! Pics might take a bit to load.

What shoes to wear with these style of dresses?
What shoes to wear with these style of dresses?
What shoes to wear with these style of dresses?
OP posts:
Tocsin · 12/02/2026 10:38

Oh, they’re crying out for shiny black knee high boots. Either exaggeratedly wide shaft with long pointy toes, or the very narrow almost sock-style with a rounded toe. Must be right up to your knees in either case.

The one thing you don’t want (for work particularly) is any type of dainty footwear - I’d avoid Mary Jane or ballet style shoes.

Essentially choose something that contrasts with (I don’t want to say negates) the innocent, girlish look of the dresses. The juxtaposition will be powerful.

Thecows · 12/02/2026 10:56

Dm's for me !

Idontjetwashthefucker · 12/02/2026 11:11

I'd wear chunky loafers or ankle boots

Alackadaisical · 12/02/2026 11:13

Tocsin · 12/02/2026 10:38

Oh, they’re crying out for shiny black knee high boots. Either exaggeratedly wide shaft with long pointy toes, or the very narrow almost sock-style with a rounded toe. Must be right up to your knees in either case.

The one thing you don’t want (for work particularly) is any type of dainty footwear - I’d avoid Mary Jane or ballet style shoes.

Essentially choose something that contrasts with (I don’t want to say negates) the innocent, girlish look of the dresses. The juxtaposition will be powerful.

Yes, knee boots!!

dogsarebetterthanppl · 12/02/2026 12:25

they look like the type of thing my auntie wore to work as a teaching assistant, she wore them with black tights and ballet flats or court shoes, which are outdated now i think. i'm a sucker for a heel but i think i'm very much in the minority, so i've attached 2 screenshots of what flats i would wear. i also don't think these dresses look right without black tights.

What shoes to wear with these style of dresses?
What shoes to wear with these style of dresses?
dogsarebetterthanppl · 12/02/2026 12:26

dogsarebetterthanppl · 12/02/2026 12:25

they look like the type of thing my auntie wore to work as a teaching assistant, she wore them with black tights and ballet flats or court shoes, which are outdated now i think. i'm a sucker for a heel but i think i'm very much in the minority, so i've attached 2 screenshots of what flats i would wear. i also don't think these dresses look right without black tights.

or sock boots.

my images are under review for me, not sure if they're showing for you.

FlowerFairyDaisy · 12/02/2026 12:27

I wear this style of dress to work at the moment with slightly chunky loafers.

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