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Original poster

Can I wear knee high boots with a dress?

57 replies

Hairyhat · 25/09/2025 22:16

I’ve just bought a lovely dress (with pockets yay!) to go to a day do. Can I wear brown knee high boots with it (for comfort and warmth) or is this a terrible idea? Will try to post the dress for you to tell me what to wear with it please. I’m 5.3 size 12 on top but more like a 10 waist (Big boobs) and I think I’m apple shape but the dress looks flattering I think. Or what other footwear would you recommend please? I was hoping to avoid heels

Can I wear knee high boots with a dress?
OP posts:
IHaveAlwaysLivedintheCastle · 26/09/2025 11:35

EvangelicalAboutButteredToast · 26/09/2025 11:18

I do think a gap between top of knee high boot and hem of skirt or dress can look quite aging style wise. Obviously on a young person it would look cool but on someone a little older I think it’s a bad look and that would be my only red flag. The hem of the skirt of dress needs to comfortably cover the top of the boot when standing.

Edited

With knee boots either the hem comfortably covers knees with no gap showing or several inches above knee with opaque tights.

I think a hem which just shows the knee cap looks terrible. Age irrelevant.

Flat laced ankle or Chelsea boots, any length is fine.

WhereDidSummerGoAgain · 26/09/2025 11:39

I think the colours of the dress are pretty autumnal and it would look great with brown boots.

Moveoverdarlin · 26/09/2025 11:43

Wordless · 25/09/2025 22:46

Good grief - how is this even a question?

Millions of women are walking around (or sitting in restaurants or at the theatre, or wherever) at this exact moment wearing a dress and boots. It’s not in any way at all an unusual combination.

(I’m actually quite … shaken that you’re so uncertain about something so commonplace.)

I totally disagree. This dress is wrong length for knee high boots. If I was wearing a short dress there would need to be a gap. A longer dress would need to come down to at least mid-calf length or ankle length.

The dress is also quite summery and by their nature, knee high boots are wintery.

Just because millions of women are walking round with a boots / dress combo doesn’t mean they look good.

Lotsofsnacks · 26/09/2025 11:49

IHaveAlwaysLivedintheCastle · 26/09/2025 11:35

With knee boots either the hem comfortably covers knees with no gap showing or several inches above knee with opaque tights.

I think a hem which just shows the knee cap looks terrible. Age irrelevant.

Flat laced ankle or Chelsea boots, any length is fine.

Edited
Show quote history

Agree, this dress is the wrong length for knee high boots, so much cooler with no gap! Midi dresses look lovely with long boots, knee length skirt and long boots often doesn’t work. Your dress looks quite summery and maybe mid calf cowboy or soft suede boots will work

IHaveAlwaysLivedintheCastle · 26/09/2025 12:17

Or what other footwear would you recommend please? I was hoping to avoid heels

Boots wouldn't be my first choice with that dress. Possibly mid calf camel or brown suede if it were cold and if I already owned them. I have very flat black suede and flat green suede over the knee boots which I'd try and see how they looked.

I don't think it would work with any of my flat laced ankle boots. I think the latter need a much longer or a much shorter length or a much fuller skirt.

My first choice would be flat ballet pumps or Mary Janes in any colour that's in the dress.

JaquelineHide · 26/09/2025 14:21

My first choice would be flat ballet pumps or Mary Janes in any colour that's in the dress.

I think this is the best suggestion.

Onlycoffee · 26/09/2025 14:25

Wordless · 25/09/2025 22:46

Good grief - how is this even a question?

Millions of women are walking around (or sitting in restaurants or at the theatre, or wherever) at this exact moment wearing a dress and boots. It’s not in any way at all an unusual combination.

(I’m actually quite … shaken that you’re so uncertain about something so commonplace.)

Seriously why so mean? Especially as you've missed the whole point of op's post. She's not asking a general question about dresses and boots, it's specific to the dress and particular boots.
Not all dresses will go with all boots. Obviously.

MorrisZapp · 26/09/2025 14:33

EvangelicalAboutButteredToast · 26/09/2025 11:18

I do think a gap between top of knee high boot and hem of skirt or dress can look quite aging style wise. Obviously on a young person it would look cool but on someone a little older I think it’s a bad look and that would be my only red flag. The hem of the skirt of dress needs to comfortably cover the top of the boot when standing.

Edited

100% this.

Original poster
Hairyhat · 26/09/2025 14:55

I’m so grateful for all these replies. Still not 100% sure what to wear with it so I’m going to try different options and see which I think are suitable for me. Glad to hear about the aging look of the gap as this is precisely what I would have no clue about!
also, might not be relevant but my legs are very skinny compared to my upper body (big boobs I’m afraid)

OP posts:
Wendywooooo · 26/09/2025 15:06

Personally I'd go ankle boots with a dress of that length, I'd wear longer boots with either a short (above the knee) or long dress with a split, but mid length I'd definitely be going for the ankle/shoe boot style

Mich57 · 26/09/2025 21:25

Hairyhat · 26/09/2025 11:03

Thanks @Mich57 I have a denim jacket. I was hoping they were still ok to wear with a dress. I’m so unstylish I never know what’s still “in” or finished

Go for it!! As long as it's not the d style hip length denim jacket 😁 I often throw on a DJ with a midi dress or wide legged linen trouser... ❤️ X

twobabiesandapup · 26/09/2025 21:46

I’m not convinced on the boots thing either, keep trying to visualise it but I can’t quite seem to! I’m also thinking perhaps ankle boots instead of knee high, but then again the right knee high boots could work, but what would the right ones look like?! Sorry OP I am clearly no help, I left my style somewhere in 2023 before my first child was born, but I do hope you find something perfect and have a fab time at the do!

RemusLupinsBiggestGroupie · 26/09/2025 22:20

EvangelicalAboutButteredToast · 26/09/2025 11:18

I do think a gap between top of knee high boot and hem of skirt or dress can look quite aging style wise. Obviously on a young person it would look cool but on someone a little older I think it’s a bad look and that would be my only red flag. The hem of the skirt of dress needs to comfortably cover the top of the boot when standing.

Edited

This is ageist bollocks. It would make a young person look cool but an older person look older? What does that even mean?

For what it’s worth OP, I think it’s the wrong kind of dress for knee high boots. It could possibly work with suede cowboy boots as a PP suggested.

IHaveAlwaysLivedintheCastle · 27/09/2025 02:09

RemusLupinsBiggestGroupie · 26/09/2025 22:20

This is ageist bollocks. It would make a young person look cool but an older person look older? What does that even mean?

For what it’s worth OP, I think it’s the wrong kind of dress for knee high boots. It could possibly work with suede cowboy boots as a PP suggested.

Show quote history

I agree - ageist bollocks.

I think a hem which just shows the knee cap looks terrible on any age.

ClaredeBear · 27/09/2025 08:04

Yes, absolutely! It would look lovely with elegant boots or quite chunky boots but the main thing it you get to be warm and stylish. Even better if you can pair it with a brown jacket.

MagicLoop · 27/09/2025 08:06

I think it would look nice. Coincidentally, 10 mins ago I read an article saying that knee-length tan suede boots with dresses is a big look for autumn 2025!

Fionuala · 28/09/2025 17:04

you could wear boots but personally i find them odd with dresses when it is not properly cold.
I wore a dress yesterday with shoes not with heels but nice looking ones.
I think they are a version of what they call Mary Janes or something.
They have a bar. I bought them in clarkes - so v slight rise to heel but not proper heel.
I think they would enhance a dress better than boots.

SecretRoses45 · 28/09/2025 17:43

Why are you asking our permission to wear boots?? 🤔

OhDear111 · 28/09/2025 18:06

It’s a summer dress. It’s got short sleeves and it’s styled with sneakers. They are clues really.

Yes, lots of cowboy boots around this year but do you want that look? Suede long boots in brown might be ok but wear a cardi or it’s not a balanced outfit. There’s lots of cardis around now! Not frumpy at all but they are being used for a preppy look. This dress is not that. Ankle boots - maybe. Heels and brown suede. Heeled loafers are good this autumn too.

Alliod40 · 28/09/2025 18:16

Personally I'd wear ankle boots but that's just me because I'm 5ft5 and long boots with it would make me look frumpy..dress is lovely though x

Lynmmc · 28/09/2025 21:26

See Good Housekeeping article " The wrong shoes". Loved it 👍

Original poster
Hairyhat · 28/09/2025 21:49

Shall I post photos of different combinations with the dress and see which you think is best? I haven’t bought my knee high brown boots yet but could rig up something for approval/disapproval? I am still clueless as to what to wear with it 🙈
I certainly didn’t expect as many responses. (I think I am starting to understand a little bit though)

OP posts:
IHaveAlwaysLivedintheCastle · 29/09/2025 14:05

OP, I assumed when you asked that you asked that you already had a pair of boots and were wondering if they would go with the dress, not that you would be buying boots specifically for it.

As a few posters have said not all dresses can be worn with boots and this might be one. I don't think knee boots that leave a gap of just the knee look good at any age. For a knee boot, the hem should be much higher or lower to cover that gap. I don't think ankle boots would be right, so you're looking at mid calf really.

OhDear111 · 29/09/2025 16:18

Longer dress - long boots. Or go for ankle boots. If dress is knee length, ankle boots.

Can I wear knee high boots with a dress?
Can I wear knee high boots with a dress?
Can I wear knee high boots with a dress?
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