Do you keep to any rules about the appearance of boots with trousers and skirts

[RememberBeKindWithKaren]

I bet I've not worded this well. Also must preface this to say I'm quite ancient and have never followed fashion as such.

In general if I wore a skirt or dress with boots, the boot would be knee high, or if an ankle boot, then it would be relatively smart. As in a bit of a heel, they'd fit round the ankle and probably not betoo loose at the top.

If I wore a boot with trousers, again they'd be smartish if with smart trousers, or more loose/ clumpy, perhaps mid-calf height etc if with jeans or casual trousers.

But now, going by images on shoe websites, anything goes at all. Which is fine if you're ok with that.

So, do you apply any rules still? Guess I'm more interested in the boots you wear with smart clothes.
Thanks in advance

Hi Magic that always used to be my philosophy but last year I got a pair of sweet little kitten heeled ankle boots in black suede and they became my go-to with smart winter skirts. So I just happened upon that combo but still feel I'm out of my depth with loose and thin fabric skirts and especially smart trousers, loose or slim- legged.

Yes and I agree with that approach when you've got the confidence to look in a mirror and make up your own mind. But the thing is that a lot of women, for a variety of reasons, don't have that confidence.

I don’t really care as long as it looks ok and I feel comfortable. Can’t think of any specific rules as such. I probably wouldn’t wear an ankle boot with a dress cos it would make my legs look shorter I think. To me boots with a dress is a more casual look, and one I quite like, but for a dressier look shoes is better.

My rule is, I put on the boots and the skirt and look in a full-length mirror. Then I think "yay" or "nah". That's it.

I wear black Docs with everything. I am ancient. I really don't care what anyone else thinks.

I wear grey timberlands with all my dresses for work. They’re comfy 🤷‍♀️

These are mine so they’re not the high ones.

I only wear ankle boots or a slightly higher type like DMs. I can’t stand knee highs or even mid calf, for me they feel dated even though I know they’ve come in and out of fashion.

I wear ankle boots with jeans, trousers and dresses. With jeans and trousers, they tend to be slightly cropped so they generally aren’t covering my boots. I don’t like that look either.

This. I like this look on so many people. Have tried so many different boots and cannot make ankle boots with skirts look even close to nice/normal on me

I generally wear plainer leather boots or suede boots with a thinner sole with smart trousers (aka the sort with a crease down the front). I then wear chunkier leather boots with more casual jeans/cords/slim cargos.

I often wear boots with 7/8 trousers or culottes as a way to extend their life beyond spring/summer as tights always seem to wrinkle around my ankles 😂.

At 50, I’m not feeling the ankle boots and shorter skirt vibe, but I’d wear the boots that you’ve linked with smart trousers or a long a-line skirt with matching tights so that my legs don’t look stumpy and ‘broken up’.

My doc martens go with everything as far as I’m concerned

But this is the thing, we are all different shapes and sizes so the "rules" that would make an outfit work on someone else might make me look ridiculous. I am short and petite with size 6 feet so have to be careful with chunky ankle boots to balance the top half out. Likewise a neater ankle boot (something like the White Stuff Willow) works for me with skirts and dresses. If I do wear ankle boots with a skirt or dress I always go for suede with a similar colour opaque tights, no idea if that's acceptable but it works for me.

I wear what I want and how I want
I wasn't aware there were rules

However the boots you shared I would never happen wear as they are pretty vile

I just wear clothes I like, I can't imagine being so insecure to have to follow rules.
What a sad way to live.

@LarryIsMyRomanEmpire thanks for that. You could have held back on the judgement but hey, you do you.

I have never really been one for rules but in the past would definitely have worn a “pretty” shoe (generally meaning with a heel) with skirts. But now comfort trumps looks for me and I cannot remember when I last wore heels. I still own 1 pair of heels (whixh I actually never wore). I love wearing my doc martens and will wear them with everything. I also love wearing sneakers and will wear them with everything. I wear smart trousers and blazers to work, with my docs or sneakers. Personally I think knee high boots are old fashioned, but maybe I missed something and they’re returning.

I’ve get skinny little chicken legs. My boots with skirts and dresses are chunky ankle lace up ones. I only have above knee or mini skirts or dresses, but when I’ve had longer dresses and put hem with long boots my legs look like they are made of wood. Long boots I wear with jeans or trousers tucked in. Skinny jeans and I are still and have always been best friends.

I know what the Op means about rules though.

20 years ago "the rule" was boots ( anything converse, knee high whatever) look better with skirts, than shoes. Then trainers came in .

I've just bought those massive UGG Tas hybrid weather shoes. Ugly as. They have models in shorts and dresses wearing them .Crazy

I’ve just bought some lovely docs and I’m going to wear them with everything. I’m 49 and I care not what the young folk think!

@Arrrrrrragghhh thanks for understanding what I'm on about 😊

Knee length boots either knee length skirts. Ankle boots ok with sort skirts.

Short

I don’t know anyone who would wear those boots like in the photo, but lots who would wear them with short skirt and tights, midi skirts, jeans and smart trousers, either straight or wide leg. I probably wouldn’t wear them with trousers or jeans but would wear them with skirts. I’m in my 40s and I’m thinking of the same age group.

I honestly don't know if there are any rules but I know what I like!
I tend to wear very chunky biker/DM style boots or Converse with skirts, trousers and dresses (maxi or mini).
My exception is with wide legged trousers where I tend to go for smaller heeled boots as I find that loose trousers and chunky boots just feels abit too clumpy on the bottom half for me.

Depends on your build IMO. I'm tall, well built and, unfortunately, have thick ankles so don't wear 'clumpy' shoes with pretty dresses and would even double check in the mirror re trainers when at the height of fashion with frocks. But casual trousers, especially wide leg, can take a chunkier style. Also, context dependent - I don't tend to wear heavier footwear if I'm dressing up. I know some would say I shouldn't be so self conscious but as I don't fit the stereotypical 'feminine' image I make efforts not to have legs/feet that look like a carthorse!