Really comfortable ankle boots

[KitschBitch]

Posting for traffic and asking for help to find a truly comfy pair of ankle boots, perhaps chelsea boot style please. I have tried Geox and Fitflop, both ok but not aesthetically pleasing. Tried Fly but too baggy around ankle - would like to wear skinny jeans over them. Very grateful for your suggestions.

Maybe I am wearing them them the wrong way! I don't mind if they are more like pixie boots and able to fit skinny jeans inside, would prefer boots to be padded inside if possible but still trendy!

Dr Marten sheepskin lines Chelsea Boots are GLORIOUS!

Moshulu do really comfy boots

Second Moshulu. I usually have to ‘wear’ new shoes in, but my new Moshulus were comfortable from day one.

Moshulu!!! 20% off some at the moment. I lusted over some in our local shop today, wish I’d succumb. I’ve had several pairs last several years, very good value.

Gabor Shiraz. Sooo comfortable.

My comfiest ankle boots ever were from shoe zone. Fit like a glove.

Clark’s Orinoco Chelsea boots. On my third pair now. Ridiculously comfortable and slim enough to fit inside skinny jeans.

Moshulu pipistrelle- gorgeous comfy suede pixie boots. I'm on my 2nd pair and wear them all the time with skinny jeans

I have a few pairs of ankle boots from Ugg which are all ridiculously comfy. They're not like typical ugg boots to look at, they're proper shoe type boots.

Josef seibel boots. They are the most comfortable boots I've ever owned. Ended up buying a second pair in the sale and wish I'd bought another one.

I always find a good pair in next, river island or new look.
As for skinny jeans imo they look awful when they are pulled over boots or tucked inside! Try rolling the jeans up once or twice above your ankle boots as they look much better!

I have also owned a really comfortable pair of boots from Josef seibel and would also recommend

I also have hotter pixie boots. I'm not normally a hotter customer but t they are funky, were in the sale and they have lasted really well.
And DM Chelsea boots. Very wide fit.
Clarks do nice styles, but not as comfortable as the above.

I've just got into Hogl boots and they're SO comfy. I got some Hogl combat boots in the sales and I wore them for the first time yeterday. I walked miles and they were so comfy. No rubbing, no marks on my feet, amazing! Some Hogl footwear is a bit classic/conservative (but then so are all the recommendations on this thread) but they have a few on-trend items and they're really good value for the quality.

Tracey Neuls do lovely comfy Chelsea boots called George but you're looking at £250:

traceyneuls.com/collections/women-1/products/george-bike-chelsea-boot-black-leather

I was going to say fitflop but you don't like them. I bought a lovely tan pair last year with gold buckle at the side, loved them so much I bought a 2nd pair.
I have got lots of compliments I think they have upped their styles so could be worth another look .