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Ankle boots that look great with dresses but are comfortable

39 replies

Newmeagain · 19/10/2026 18:33

I am really struggling to find some nice ankle boots that will also be comfortable. I used to have some great ones from Russell and Bromley. I would prefer not completely flat - just a one inch block heel.

i bought some of those slightly taller chunky Chelsea boots that everyone has been wearing but I think my ankles are too narrow for them and so my heel moves and they are really uncomfortable.

OP posts:
GreenEyesMillennial · 19/10/2026 22:40

I like the barbour ones! Super comfy

NescafeAndIce · 19/10/2026 22:41

The only comfortable ankle boots I've had are from ECCO and they're great - can walk a lot in them.

HorseandHeron · 19/10/2026 22:53

I'm looking for some too. I bought some gorgeous ones from Fitflop about 8 years ago and they are finally wearing out. I could walk miles in them every day. But I hate the styles Fitflop have now. Just want a simple Chelsea boot with a low heel that is comfortable for walking miles in the city.

MsOtisReflects · Yesterday 07:10

These are rather elegant:

https://www.grenson.com/ingrid-womens-chelsea-boots-in-black-leather/

(I tend to prefer the clumpier Grenson boots and shoes.)

Have a look at the rest of their boots if the pair I’ve linked aren’t quite what you want.

Mrsmooja · Yesterday 10:30

I second the PP who suggested ECCO. Super comfortable, last forever and stylish

BandyUrnham · Yesterday 11:04

Get ones that fit properly - too big and your feet will slop about in them.
Lace-ups are better for fit.
I have some Grensons but not 1 inch heel.

With chelsea boots, if you need a half-size, don't get the nearest size up and insoles because it almost certainly won't work.

Arabella | Womens Triple Welt Boots in Black Leather | Grenson
They're not these but similar idea

Gabor might be worth a try.

BandyUrnham · Yesterday 11:12

GreenEyesMillennial · 19/10/2026 22:40

I like the barbour ones! Super comfy

They are.

KnickerBockerGloriously · Yesterday 12:58

I have slim feet and ankles.
I'd suggest you look at Dune, Geox, Mode in Pele and even good old Clarks. I usually have to add an inner sole and wear thick socks.

LadyUrsula · Yesterday 13:23

There's a good range of ankle boots here and they'll be discounted around Black Friday (sometimes up to 50%). I'm usually a size 7 but need a size 8 with Memery. Exchanging for different sizes / styles is easy.
https://memery.co.uk/collections/womens-boots

teaandabun · Yesterday 13:29

Can I please ask which of the Ecco ones are you finding comfortable? I’m on the lookout too.

NescafeAndIce · Yesterday 13:39

teaandabun · Yesterday 13:29

Can I please ask which of the Ecco ones are you finding comfortable? I’m on the lookout too.

It's the ECCO Dress Classic Chelsea boots - I bought them two years ago but assume they're the same?!

GigiAgnesStar · Yesterday 13:40

I got a pair from Matalan a couple years ago that are really comfy!

ginasevern · Yesterday 13:43

I got some some Fat Face a few years ago and are super comfy and go with just about anything, including dresses.

HeinousBeaker · Yesterday 13:43

It might not be the look you want but I have narrow feet and ankles and I love my doc Martin Chelsea boots

JackieGoodman · Yesterday 13:46

I have these, lovely, also available in black and brown, very light and comfy.
(I have slim ankles and they are neat and not gappy) edited to add this and to update link

Remonte

PineappleSunrise · Yesterday 13:47

I’ve got these to wear with midi skirts, they’re beautiful and comfy and not made in a sweatshop. I have the “50” style (linked) which has a higher slimmer heel, but you can also get a “20” style with a lower block heel.

https://www.anoncph.co.uk/collections/ankle-boots/products/vully-50-stiletto-soft-calf-black

eta: You can find them on Vinted and eBay if you want to save a few pounds on them!

Aggieforme · Yesterday 13:48

I wear Blundstones. Extremely comfortable and hard wearing. Last for years and imo look good with dresses.

teaandabun · Yesterday 14:06

Thank you for the Ecco details, Bandyurnham and NescafeAndice. Will check it out.

lookatmylife · Yesterday 14:13

I second the DM Chelsea boot recommendation if you want a slightly chunky look. I wear with short dresses and tights and long dresses.
They look good with turned up jeans too.

BandyUrnham · Yesterday 14:28

@teaandabun , I only supplied the link but thanks. It's really good of you.
The boots are nice but not 'me'.
I have Dealer Boots (like DMs but better quality) as chelsea boots, but have a smarter pair of ankle boots with zips that are ancient but smart, the Grenson lace-up ankle boots. The dealer boots get worn most.

BeardySchnauzer · Yesterday 16:04

I have a really comfy pair of heeled ankle boots from Clark’s that also look good

the comfiest ankle boots with block heel I have are a cheap suede effect from asos. Could walk for miles in them!

Yello24 · Yesterday 16:08

I’ve been wearing the Clarks Orinoco for years. Pretty classic and good value for a well made leather boot. Have brown and black and wear them with everything all winter

Daftypants · Yesterday 16:17

I have Gabor ankle boots in black suede so they look quite smart .
Come in half sizes which helps get the best fit and I have very slim narrow heels so my feet don’t slip about in them .

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