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

@RememberBeKindWithKaren I was a teenager twenty years ago when women’s shoes were generally quite delicate and anything chunky was unfashionable. (The exception to this was DMs - they’re more in fashion now than they were then but DMs seem to have always endured in some form). So, we wore lots of ballet flats (my feet were so sore!) and I think Mary Janes (ugh) even came back in for a while.

I would describe recent styles as more ‘clashy’, e.g. chunky trainers or big boots with a nice dress. While I still struggle to get on board with the look of trainers as described (which really doesn’t matter - comfort is much more important), I’ve come to love boots of many kinds with more delicate items of clothing like skirts and dresses. Somehow they just look great and, like the enduring popularity of DMs, I think this look somewhat transcends fashion. I would say go for it.

Having said the above about ballet flats, they have also crept back into fashion this year! I won’t be going there!

I bought two pairs of boots last weekend. https://www.gaborshoes.co.uk/womens-c1/boots-c3/knee-high-boots-c101/gabor-garden-womens-knee-high-boots-p52601#attribute%5B1%5D=32890
And
https://www.gaborshoes.co.uk/womens-c1/boots-c3/chelsea-boots-c75/sallis-ladies-ankle-boots-p45487#attribute%5B1%5D=1283

I've worn the knee-high ones with a just-above-the-knee dress and with a longer skirt, but have only worn the chunky ankle boots (and also my lightish brown chelsea boots) with trousers.

I would never wear those boots the previous poster mentioned.....its the soles.
Just a weird 'me thing' but the only times Ive ever slipped or tripped have been whilst wearing those very flat soles.
I feel like they've got it in for me at this point!😂

Those Balmoral boots are gorgeous. Out of my price range, sadly.

I’m not often in the shops, hate buying on line

Now I’m seeing your difficulty! I too am very rarely in physical shops, but scarcely a day goes by when I’m not browsing online. I actually buy very little but know exactly where to look for what I want, am always coming upon new sources and generally, perforce, have an idea in my head of styling and proportions that look wearable and current. If you’re not constantly (or regularly, or even occasionally) interrogating the ‘What’s New’ pages of websites and seeing how they style things, it may well be trickier to judge what you feel you can wear.

(That’s a question!)

I LOVE the look of docs with dresses and skirts. But I think it only looks good on those with skinny legs - which I do not have sadly. I refuse to wear heels (feminist issue for me) so I wear knee high boots (flat) with fancy dresses, and my doc boots or Mary Jane’s with fancy trousers.
I’m not overweight but I have chunky calves and if I wear a dress with docs I just look awful. Which sux cos I love the look.

I agree that knee highs are a bit dated but it depends on the ones you get. With a heel and fancy or sock - yes. Flat and chunky - no. Just my opinion though what do I know - I’m ancient.

I lived in docs and short tea dresses in my 20s. I’ve always had chunky calves, but that seemed to work for me as far as I can recall. Definitely depended on the skirt/dress shape and what I wore on top though.

I really wish I’d kept the couple of pairs I had, they were properly vintage and buttery soft but I think they went in a clearout about 10 years ago.

I’ve suspect knee highs might have a resurgence this year. There’s a lot of them around.

Im currently wearing some
docs with a pair of black joggers 😂 but I’ve always been weird and not really bothered about fashion/social norms.

I don’t follow any rules. I scandalised my family by getting married in docs!

Just the one, Getting?

Nah, I just wear what I want, when I want, rules are boring!

I'm ok with pretty much anything except those trousers which sail around mid calf. I always assume some misogynistic designer sketched those.. even our newsreaders on TV look terrible in them.
Then there are the sporty leggings that go right up your behind.. no, absolutely NOT, no matter how young you are & how perfect your figure is. That, I DO not want to see..

There's boot rules?
I wear my chunky ankle boots with everything from dresses to cuffed cargos to jeans shorts.

Knee highs generally with dresses although I have worn them under boot cut jeans before if the toe looks better than other foot attire but I never knew there were rules....
Wear what you like 😄 life's too short and I doubt anyone else would say, oooh she shouldn't have worn that style of boot with that skirt 😉✌🏼💖 and if they did their opinions should mean nothing to you. Wear it/them because you like it and do it with confidence 🙂

The only look i don't like is boots just below the knee and skirt just above- I think it works better where you have either more leg showing between boot and skirt (so a mini with knee boots or shorter boots with a knee length skirt) or else no gap at all (today I am wearing a midi skirt with knee length boots so you can't see my legs at all). If there's a gap it needs to look intentional.

I really like those sock boots but I think you need long legs for them.

I think we are in an absolutely anything goes fashion era.
I was thinking about this the other day.
Any stylr jeans, any style shoes, any style dress.
I think in this era you can choose a base style like boho, urban, alternative etc. But you dont have to stick with it day to day.

I usually wear a black pair of Chelsea boots with skirts but last weekend I had on a midi dress and wore some faux suede Cowboy boots instead, and I got a compliment on this from my friend.

I'm with you 100%. on mid-calf trousers. I'm just never going to wear them. so weird !

@RememberBeKindWithKaren
They come 'back into fashion' every few years, it doesn't matter how many times, I'm always going to think they're unflattering!

Not sure if I do need to say this but anyway I wasn't literally expecting to be told if anyone keeps to any rules. It was meant figuratively, so as to inspire people to think about what kind of boots they like, what people think looks good with what, what styles/ colours/ any other modifiers of boots will go with what and then , for me to read it all and mull it all over.

Please don't get hung up on the word " rules ".. It isn't literal.

Thanks to everyone who is still adding their comments, it's giving me so much food for thought . Really helpful.

If anyone is interested, I'm juggling my job with a quite hands-on caring role for my elderly mum and I haven't been into a physical shop with the aim of buying myself clothing or footwear in months. When I do know- or when I think I know -what I need for winter, I'm going to carve out some time for myself and tootle round the shops..

@cornflakecrunchie me too. you and me against the fashion world :)

@RememberBeKindWithKaren
Absolutely, lol!

Enjoy your shopping day when you get chance!
(Looked after my late mum, too, not easy, hugs.)

Very envious of @IHaveAlwaysLivedintheCastle's boot collection. My shoes have mainly been replaced by boots and trainers, all very solid looking and most with platform soles. I have ankle and knee-high boots; I don't like calf-length on myself although have worn them plenty.

I wouldn't wear those sock boots, OP, but do wear visible socks and am not sure what I think the difference is! They would, I think, look right with a longish satin or lacy skirt - and with any trousers you'd pair with 'nice shoes', given the boots' slender profile.

With your knee-length winter skirts, it might be worth trying the sock boots over long socks, the socks folded down over the tops of the boots. Depends on your individual shape & style, of course.

Thank you. The over the knee boots are all pre- Covid by some margin. The black suede are Stuart Weitzman and they are at least 8 years old. Stuart Weitzman is still selling pretty much the same boot. The green suede are Jigsaw and they could be 10 years or older. The leather ones are Duo and they're the same era.