Rules of Boot Wearing

[Pinkwitcheshat]

For some reason I never find autumn/winter footwear as straightforward as summer, when my trusty Birkenstocks / white trainers seem to go with most of my wardrobe and be (reasonably) fashionable.

So what are your rules of boot wearing for 2021/2022? I'm favouring:

• Flat chunky boots with jeans slightly cuffed/rolled, a bit of sock showing is ok as the days get colder

• Slightly smarter, low to medium heeled Chelsea type boots with black tights and skirts/dresses for work (chunky biker style boots not appropriate in my office)

• I've put my stiletto boots away at the back of the cupboard as they feel dated now (sob). But I have some chunky heeled boots which I think (hope) are still reasonably modern??

• I will only be wearing knee high boots over jeans if its wellington boots or my Ariat boots for country dog walks. But are flat black knee highs ok with a skirt and thick back tights for work/general wear?

Come on and sort me out fashionistas

(Caveat - I firmly believe women should dress to please themselves and no one else and you should rock your boots however you please, I'm just personally trying to look a bit more "current" and not completely out of date after feeling like I lost my way a bit, which is why I am posting in S&B section)

I'm wearing Toast Jade boots with slightly rolled up dungarees or midi kilts
Solovair dealer boots with opaque tights and shortish skirts or dresses, or skinny plaid trousers
Knee high cowboy/riding type boots with leggings and skinny jeans
Might wear boilersuits and dungarees with 8 hole solovair derby boots

or will do when the weather gets colder

also will wear non clumpy chelseas and ankle boots if I need to look more dressy.

will probably wear shoes or trainers with straight jeans and maybe the dealer boots

I don't get this rules business. Beyond practical considerations, I tend to look in the mirror and see if I like the look. Perhaps I'm behind the times...

Me too silvery, but I'm the one who has crocs and birkenstocks from many years ago and kept on wearing them.

Rules:
Are the shoes/boots comfortable and suitable for what I'm doing
Do they look ridiculous with the rest of the outfit - if they do, I might need to take a change of footwear with me

I’m using “rules” in a lighthearted, tongue in cheek manner.
Obviously there are no actual rules….

I am also trying to work out what to wear with jeans?!

I have mom jeans that I have been wearing with trainers but have no idea how to wear them with boots or if it is even possible?!

And to PPs who say everyone should wear what they want/is practical etc we all know this to be true but I would also like to try and look 'current' as does the OP! This is the style board after all!!

The only 'rule' is to dress for your figure and for comfort and self confidence.

I agree @Hoviscats

Some women just want to be comfortable - that is fine

Some women don’t give a toss about fashion - that is fine

Some women do give a toss about fashion and want to look current and stylish - surely that is also fine????

@Pinkwitcheshat you've been getting some weird answers here today as people have entirely misread your tone

I'd disagree a bit with this

- Slightly smarter, low to medium heeled Chelsea type boots with black tights and skirts/dresses for work (chunky biker style boots not appropriate in my office)
I always feel a bit militarily or traffic warden-ish in skirt/ black tights/ flat boots so tend to have patterned or woolly tights instead

And no more knee high boots over jeans for me at all.

Thanks @BlueCowWonders

And no more knee high boots over jeans for me at all

What would you wear for long walks in deep mud then, or is that not part of your lifestyle? I live semi-rurally and for long muddy dog walks people are still in tight skinny trousers under wellies / Ariat / Dubarry style boots

@Pinkwitcheshat I'm wearing my skinnies for dog walks with wellies. Impractical not to.I still wear trainers with jeans in winter and will be wearing them with wide legged jeans.Have DMs for slim fit jeans and rolled 501s.Chunky loafers are all over the place at the minute so would be good for work?I would like some Grenson ones but will have to be a cheap copy.

Oh and I've been trying on flat black knee highs to wear with jumper dresses.Can't find any I like though.

This week's Grazia answers:

No ankle boots and skirts/dresses. I think it looks odd.

Also:
Stiletto boots fine with midi, it seems

Long flat boots:
"hot girl autumn well underway so wear with thigh-skimming minis and bare legs"

I just wear... ankle boots but with certain dresses. Got some nice Top Shop black leather ankle boots but need reheeling.

Got some old Ugg moccasin style boots which I wear with jeans.

Got some lovely grey suede knee high boots which I wear with dresses etc.

Have some Ash Jalouse grey boots which I wear with a lot - jeans, trousers, dresses etc.

Got some nice black suede tab Natura ankle boots which I wear with various skirts, dresses etc but they need the inner sole repairing and reheeling.

Considering buying trendier boots. Never really liked Chelsea boots, riding style boots almost always think they look better with horses, never really liked cowboy boots either.

I think do what you want. If it looks ok to you, wear it, if not, don't.

@Palavah

This week's Grazia answers:

Some of those Grazia boots are absolutely vile.

Hate nearly all the Grazia boots!

I just bought some solovair high shine dealer boots.I will wear them with slim jeans rolled a little above, long dresses and with work skirts and dresses.Expensive but I can't find what I want cheaper and they should last forever.

Interesting to know old you are. Only thing I gave up at a certain unmentionable age, were high heels and jeans. I love the block heels too. Otherwise anything goes so long as I feel happy at my reflection.

What's wrong with knee high boots and jeans? I like the look and find it very practical for autumn and winter.
I personally don't like ankle boots with skirts or dresses.

I’ve noticed a few women this autumn in sleeker/smarter knee high boots over jeans and I do feel it looks very dated, but like anything if you like it & find it comfortable & practical that’s what matters.

@Pinkwitcheshat

I’ve noticed a few women this autumn in sleeker/smarter knee high boots over jeans and I do feel it looks very dated, but like anything if you like it & find it comfortable & practical that’s what matters.

I think I'm a bit long in the tooth to care about looking "current" to be honest. I'm loving this thread, the idea of "rules" appeals, (even if I choose to ignore them).

What about DM Boots? I’ve wanted some for years, now I’ve got some but I don’t think they go very well with any of my clothes!!