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What are stylish people wearing on their feet and ankles this winter?

45 replies

Rainallnight · 05/10/2026 16:12

I’ve struggled with this question for ages. What shoes and boots would make me look vaguely current? And talk me through the relationship between trouser length and shoe/trainer/boot style. Please!

I’m quite short so very tall boots aren’t great.

OP posts:
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Girlwithavibe · 05/10/2026 17:23

Socks and shoes lol sorry I couldn't resist I would just wear what u love and what suits your unique style and then u will be stylish

Rainallnight · 05/10/2026 22:15

I see what you mean but I’m looking for advice, thoughts, inspiration. This is S&B after all!

OP posts:
JaneJeffer · 05/10/2026 23:10

In my opinion the footwear options at the moment don’t suit the clothes options.

TealReader · 06/10/2026 10:42

Stylish is relative and personal. What sort of trousers do you like to wear? Are you on your feet all day? Do you have any particular needs in shoes? For example today I’m on an admin day at work. I’m wearing wide leg washed black jeans with grey loafers. Yesterday I wore full length khaki barrel trousers with some little green/beige jazz shoes from camper. I don’t know that I’m current but I know my style if that makes sense!

I’ve spent a fair amount of time looking at shoe options this year. I realised I had too many black shoes so have worked to add some more neutral/coloured options. I seldom wear heels because I’m on my feet all day. When I buy heels I don’t spend much on them because they are seldom worn. I have had Achilles issues and plantar fasciitis so I prioritise comfort. I spend a lot on my everyday shoes because comfort is important to me and shoes get worn so much.

NorWouldTilly · 06/10/2026 11:30

Having habitually oscillated between knee high and and ankle boots all winter for years - right now I feel this looks fresher and offers more opportunity for sock experimentation:

What are stylish people wearing on their feet and ankles this winter?
What are stylish people wearing on their feet and ankles this winter?
NorWouldTilly · 06/10/2026 11:31

@Girlwithavibe you must be completely new to the Style & Beauty board?

FckThisShit · 06/10/2026 11:40

I work with the public, youngsters and students are all in sports trainers, so if it's trendy you want that's it. Stylish is more dependant on the other clothes you wear, if you're in a pencil skirt then cowboy boots just won't do IYSWIM.

What is your day to day wear?

SheilaWilde · 06/10/2026 11:46

I generally wear Blundstones or lace up brogues as I’m on my feet nearly all day and generally wear wide legged 3/4 trousers or big skirts/dresses. @NorWouldTillyI love the black lace ups, do you know where they’re from?

SheilaWilde · 06/10/2026 11:48

SheilaWilde · 06/10/2026 11:46

I generally wear Blundstones or lace up brogues as I’m on my feet nearly all day and generally wear wide legged 3/4 trousers or big skirts/dresses. @NorWouldTillyI love the black lace ups, do you know where they’re from?

I just re-read your actual question, sorry 🤦🏻‍♀️ I’m not implying I’m stylish 😂

NorWouldTilly · 06/10/2026 11:55

The plain black are Prada (see photo). The embroidered pair are Simone Rocha.

What are stylish people wearing on their feet and ankles this winter?
MyManinCaracas · 06/10/2026 11:59

I’m not going to act like I think these are stylish but they are very comfortable and look nice with jeans. Gabor which I have read is for those of us at death’s door.

MyManinCaracas · 06/10/2026 12:00

Hmmmm

What are stylish people wearing on their feet and ankles this winter?
NorWouldTilly · 06/10/2026 13:57

Thanks, @Librarina- I’m a sucker for the sort of socks only Elon Musk can afford, so need constant reminders that Community Clothing exists.

LadyUrsula · 06/10/2026 14:14

I don't know your age group but I'm over 60, average height and will be wearing ankle boots most of the winter. I have leather & suede ones in most colours, some completely flat and others with a small heel. I usually wear them with narrow (not skinny), straight trousers & jeans. Most of mine come from Moshulu.

If I'm wearing a winter dress, I usually wear dark tights in a matching colour and vintage style shoes from Memery (I buy mine in their sales - next one will be the Black Friday sale)

https://memery.co.uk/products/40s-vintage-style-pumps-in-suede-with-rosette-plum-luise

1940s style suede pumps with a rosette - Plum - Luise

Plum 1940s-style suede pumps with a rosette. Elegant 6.7 cm heels and a softly rounded toe for a glamorous vintage look.

https://memery.co.uk/products/40s-vintage-style-pumps-in-suede-with-rosette-plum-luise

RobinEllacotStrike · 06/10/2026 17:01

Uniqlo's socks are fabulous and come in a rainbow of colours - 4 pairs for £12.90

I've had the same pairs for years but usually get a few more colours each year (to replace the ones DD steals)

www.uniqlo.com/uk/en/products/E482605-000/00?colorDisplayCode=91&sizeDisplayCode=025

Rockpunkdisco · 06/10/2026 17:06

Will continue to wear my comfortable paver boots in several different colourful designs! The DM style but for comfort lol 😆

NorWouldTilly · 06/10/2026 17:52

Well, I spoke as someone of a similar age and size to you, @LadyUrsula - didn’t think to mention it as my footwear choices aren’t really age or size dependent. I just wear what appeals to me.

Jonesmaximus · 06/10/2026 20:47

NorWouldTilly · 06/10/2026 11:30

Having habitually oscillated between knee high and and ankle boots all winter for years - right now I feel this looks fresher and offers more opportunity for sock experimentation:

Oh god if this is current fashion I'm delighted to be wearing Hush puppies!

Princessfluffy · 06/10/2026 20:57

I’m really into the shoe/sock combo experiments

fuschiaproudparrot · 06/10/2026 21:01

NorWouldTilly · 06/10/2026 11:30

Having habitually oscillated between knee high and and ankle boots all winter for years - right now I feel this looks fresher and offers more opportunity for sock experimentation:

Oh for goodness sake 😂

DevastatingFinish · Yesterday 16:48

I don’t know if these are stylish, but I like Toast and got these there, and also recommended by Esther Walker who embodies a certain type of aspirational NL mum, and they are very comfy and I really like the look

What are stylish people wearing on their feet and ankles this winter?
KateBushAgain · Yesterday 17:28

Converse high tops or DMs with barrel leg trousers .
Flat trainers with cropped wide legged jeans .
Knitted tights with platform brogues for dresses .
I’ve a nice pair of R&B knee highs for leggings , shirt and blazer combo .
I’m always on the lookout for socks to wear with my lace ups á la Prada’s vision .

Boobyslims · Yesterday 17:34

I am thinking the same, OP. I am drawn to the chocolate leather slouch and pointy boots with a low heel that are popping up everywhere. It feels a bit 90s again.

boots seem to be flat and wide on the calf.

I want the ankle boot to come back… I spotted straight leg jeans back on Anthropologie and a normal length, oh joy!

anyway, back to covering our feet. Continue!

OneNewEagle · Yesterday 17:39

No idea following to see some ideas. I need flat and wide fitting due to my disability so really struggle to find decent footwear.

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