What shoes to wear under rolled trousers that you won't freeze

[Tinimineymoo]

I mean those mums jeans or toast type rolled up trousers. They do look good with trainers or loafers, but as soon as I wear them with boots, especially heeled ones, they go from cool to ugly and frumpy. Is there any footwear that won't make me get a uti and will still look good? Any tips?

Why would you get a uti from cold ankles?

But aside from that, high top trainers look ok with rolled up jeans.

Cold feet and ankles, and uti have high correlation for me! The boot and high waisted mum Jean combo is not a good look is it?

Anything other than high top trainers? Those converse types are also kind of cold and bit too young for me.

The problem in those pictures is that the boots are pointy. Round or almond-toed chunky boots look fine

Oh interesting! And flat instead of heels maybe? doc marten types would look too chunky though, so ankle boots that are a bit less bulky. Any ideas?

Isn’t the gap the thing that makes all the difference? I wear skin pop socks with my boots and slightly cropped trees.

I just wear thick socks with trainers or thick soled shoes (like loafers). I haven't mastered boots with them yet apart from lace up ones

@Tinimineymoo I wear mine with chunky-soled Chelsea boots (mine are from Air and Grace). I think the rounder toe balances out the broader leg.

And yes, definitely flat.

I wear Vagabond Cosmo 2.0 chunky soled chelsea boots with rolled up jeans, love them

This is all very interesting to me. I have no sense of style but care about comfort. I hate having cold ankles, so if there's a way of having cosy ankles but some kind of rolled up jeans/ boots thing I'd like to know what looks best! I find the fabric of the trousers has more bearing on giving me a uti or not than the ankle temperature.

Laced up ankle boots- flat ones
Never heard of cold ankles causing utis

@Dontfuckingsaycheese

Isn’t the gap the thing that makes all the difference? I wear skin pop socks with my boots and slightly cropped trees.

You are right I think, maybe the skin show is the true soul of this style and they are just not meant to be with anything else. But will def try the round-toed flat ankle boot idea.

@Dontfuckingsaycheese what are skin pop socks?

Off to google chunky sole Chelseas :) thank you for these ideas.

Actually I have vagabond chelsea boots too that I wear with these kind of jeans.

I wear long socks - often stripy ones, but also school socks from the M&S girls’ department - and either trainers or DMs.

I wear long socks (knee high merino) and lace up flat boots too with chunky sole (but not too chunky, I’m not into the tractor styles a la Ganni). Trainers work well too.

Blundstones work too with some of the styles.

Thick socks & docs or dupes of chunky balenciaga boot, leather clogs, fleece lined berkenstocks, high top trainers inc ones with tractor sole.

Are you sure you mean UTI?

Chunky doc martens are perfect for the rolled up jeans!! They've had a huge surge in popularity to match the trend in cut off length trousers if you ask me.

@Tinimineymoo
Invisible skin colour - knee-high pop socks. Well invisible as long as you don’t get up really close to me! So slight warmth. And legs look slightly less pasty.

Oh - and trews!! I don’t wear slightly cropped trees 🤔

How can you get a urinary tract infection from getting cold ankles?

I have this same problem! I can wear boots with jeans rolled up, but no other rolled up trousers. I love dungarees and boilersuits with trainers, but they look so shit and yes, frumpy, with boots (when I do it). I've honestly resigned myself to only wearing jeans in winter. My dungarees, boilersuits and other trousers only come out when it's no longer mandatory boot season.

Thank you @Dontfuckingsaycheese been here 30 years, had no idea they were called pop socks!

@MidSizeMillie I hear you. I love summers with short, rolled up relaxed trousers, dainty dresses and skirts, early autumn combo with biker jackets but as soon as it gets seriously cold, the only thing I can wear is straight cut jeans, and it starts to feel very boring...

pp questioning UTI - I am a biased sample of 1, and maybe it is the ankles and too thin shoes so I don't know, but there has been a high correlation. But even if this isn't the case for most, the frump-look problem is possibly universal.

I wear my dM Chelsea boots and long knee length wool socks under the jeans. I sometimes wear heat tech leggings too underneath for added cosiness