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midi length work dresses-what to wear on feet/legs?

51 replies

Allaboutsleeves · 01/03/2026 07:41

I like to dress smartly for work and would like to move towards wearing more dresses . I am middle aged.

I have recently have found myself always in trousers with a nice blouse as i am struggling with what to wear on my legs / feet with a dress and would like something age-appropriate. i love lots of the dresses by MeandEm etc but the models are younger and wear bare legs ( fine for me in summer with tanned legs) and trainers or short boots which i don't think are right for me.

Do any of you style-conscious older ladies have any suggestions for appropriate footwear and leg coverage to help me out of my dress-avoiding rut please?

OP posts:
ScoutOfTheSoftHeartsClub · 02/03/2026 11:17

@Storynanny1 would it assist you to hear that for the last two years all the most fabulously stylish tourists in my local city have been parading through spring and summer in high calf (often cowboy) or knee high boots with shortish but not extreme mini length skirts?

Storynanny1 · 02/03/2026 11:39

ScoutOfTheSoftHeartsClub · 02/03/2026 11:17

@Storynanny1 would it assist you to hear that for the last two years all the most fabulously stylish tourists in my local city have been parading through spring and summer in high calf (often cowboy) or knee high boots with shortish but not extreme mini length skirts?

haha! but are they short 69 year olds?!!!

Newmeagain · 02/03/2026 11:49

I work in London (professional services) and don’t really see any high heels, except for a few older women (I am older but don’t wear high heels).

it’s manly trainers or boots, loafers and Mary Jane’s.

it is a bit of a fashion dilemma- I am currently contemplating buying some loafers but I am very undecided…

HelenHywater · 02/03/2026 14:48

I've got some block heeled Mary Jane shoes that I wear with midi dresses/skirts with tights if I want to look smarter. Also some heeled boots (knee boots).

I'm happy wearing single colour trainers or loafers too.

I refuse to wear high heels these days. A few women in my office do wear them and they look very dated. All the younger women are wearing loafers (and opaque tights) or trainers.

TerracottaWorrier · 03/03/2026 03:15

Not an older lady but I think the answer is some kind of clog or chunky mule. They have a good balancing effect with a dress. Otherwise you can have dolly legs.

ScoutOfTheSoftHeartsClub · 03/03/2026 06:06

@TerracottaWorrier - if you read the first line of the OP you may want to reconsider your suggestion …

TerracottaWorrier · 03/03/2026 06:23

ScoutOfTheSoftHeartsClub · 03/03/2026 06:06

@TerracottaWorrier - if you read the first line of the OP you may want to reconsider your suggestion …

Sorry. I felt too enthusiastic about the clogs. 💔

holidayonkirrinisland · 04/03/2026 07:19

Following a PP’s comment, I just came on to speak up for Hilda Ogden: she scrubbed up well.
”What does that lipstick taste of?”
”Woman, Stanley, woman.”

Wildviolet · 04/03/2026 07:43

holidayonkirrinisland · 04/03/2026 07:19

Following a PP’s comment, I just came on to speak up for Hilda Ogden: she scrubbed up well.
”What does that lipstick taste of?”
”Woman, Stanley, woman.”

Hilda was a style icon. There can few women with such an instantly recognisable look and she certainly had a capsule wardrobe!

holidayonkirrinisland · 04/03/2026 07:47

Wildviolet · 04/03/2026 07:43

Hilda was a style icon. There can few women with such an instantly recognisable look and she certainly had a capsule wardrobe!

She ( Jean Alexander) had beautiful skin.

HummingBird50 · 04/03/2026 07:49

I saw a woman wearing low-heeled brogues and a dress, looked stunning. Am trying to find some as I will defo invest for spring/autumn. Boots for winter and sandals for summer with my dresses. I do prefer a heel though, even though I'm quite tall.

myladyjane · 04/03/2026 08:46

So can I ask re the tights thing. I am just awaiting delivery of a denim shirt dress https://www.marksandspencer.com/pure-cotton-denim-midi-shirt-dress/p/clp60778348?color=DENIM&extid=ps_ps-pla-pmax_ggl_ww_ch__-UK-_-_bau&cq_src=google_ads&cq_cmp=20011577753&cq_con=&cq_term=&cq_med=pla&cq_plac=&cq_net=x&cq_plt=gp&gclsrc=aw.ds&gad_source=1&gad_campaignid=20014443268&gbraid=0AAAAAD7g6bRph44XNy-w8pYnpDy-Hdlxd&gclid=EAIaIQobChMIpaXbq-yFkwMV7ZRQBh3hmzNKEAQYAiABEgJyJfD_BwE

i have some green pointed flats, some tan ones, some chunky snakeskin loafers, some black knee high boots, some tan knee high flat boots and some ankle boots. Also many many trainers. In the summer I’d be ok with the flats and bare legs. In the cold I’d be ok with the knee high boots and some tights. But in the spring, what do I wear between the shoes and the dress? That’s the bit I get stuck on.

M&S

Pure Cotton Denim Midi Shirt Dress | M&S | M&S

Breeze through the warmer months in timeless style courtesy of this denim shirt dress. It's designed in a regular fit, with a button-through fastening and an elasticated self-tie belt that cinches the waist. This short-sleeved piece is finished with a...

https://www.marksandspencer.com/pure-cotton-denim-midi-shirt-dress/p/clp60778348?color=DENIM&extid=ps_ps-pla-pmax_ggl_ww_ch__-_UK_-_-_bau&cq_src=google_ads&cq_cmp=20011577753&cq_con=&cq_term=&cq_med=pla&cq_plac=&cq_net=x&cq_plt=gp&gclsrc=aw.ds&gad_source=1&gad_campaignid=20014443268&gbraid=0AAAAAD7g6bRph44XNy-w8pYnpDy-Hdlxd&gclid=EAIaIQobChMIpaXbq-yFkwMV7ZRQBh3hmzNKEAQYAiABEgJyJfD_BwE

ScoutOfTheSoftHeartsClub · 04/03/2026 08:57

I wouldn’t bother trying to wear that dress until the weather is warm. Think it would look clumsy with jumpers and winter footwear. You could wear it with (hidden) socks for warmth under knee high boots in spring but I’m not sure it’s the right dress for that.

holidayonkirrinisland · 04/03/2026 09:04

ScoutOfTheSoftHeartsClub · 02/03/2026 10:16

I’m not happy about the return of tights. I’ve loved the years of stomping about in gently hued, calf length Margaret Howell socks under ankle boots or summer footwear. In fact socks with skirts is probably one of the main reasons why I hardly ever remember jeans exist.

I love this crew socks with skirts look, but keep wondering if I’m too old for it ( 62): you sound very stylish.
Off to look at MH socks.

dudsville · 04/03/2026 09:14

I think with things the younger folks are doing, it isn't so much that it doesn't look right on older folks, but our eye isn't prepared to see it when we look in the mirror. Much like when we transition from winter wear to summer wear and suddenly sandals look weird. By the end of summer they look right and then boots look weird.

A long time ago when white trainers with dresses took off, I couldn't do it because I felt like that kid in school trying unsuccessfully to look like one of the popular girls. Now that the trend is over (classic but dated) I feel like I can finally embrace it, and with that, I'm embracing that my style may be dated from now on when I wear that style.

So, all that said, why do you think trainers and short boots don't work for you?

I'm off to dig out my old loafers and brogues to see what they're like.

HappyFace2025 · 04/03/2026 09:15

Storynanny1 · 02/03/2026 11:39

haha! but are they short 69 year olds?!!!

Indeed! I was wondering the same.

Gettingbysomehow · 04/03/2026 09:17

In summer I wear dresses with flat sandals, smart ones not frumpy ones.
Winter I'll wear sock boots or smart ankle boots with a heel or courts. I like pointy toe courts the best with a fsirly low heel.
I have nice feet at 64 so I can wear what I want and prefer modern styles.
Trainers with midi/maxi dresses look ghastly. You could probably get away with them with a short slim fitting dress.

ScoutOfTheSoftHeartsClub · 04/03/2026 09:29

@holidayonkirrinisland - Thanks! I’m actually a little older than you and, IIRC, I probably absorbed this style from Carla Sozzani / Vogue in the early-ish noughties. The women doing it best all seemed much older than me (though they probably weren’t).

It was this sort of thing (afraid I don’t know this site at all but it came up on Google):

https://www.disneyrollergirl.net/ankle-socks-for-every-age/

As I said, I wore this for years, so was very ready for a change and am loving knee high boots right now.

The-Dancing-Babushka

Ankle socks for every age

I found this great photo in National Geographic at the hairdressers (I go to Cuts in Dean St – v good if you want short hair). It reminded me that I’ve been planning a post on women in …

https://www.disneyrollergirl.net/ankle-socks-for-every-age/

Supersimkin7 · 04/03/2026 09:30

Sheepskin insole makes smart footwear warm enough.

Try thick socks poking out of the top of boots or trainers. Slight stumpy effect offset by 21st century verve.

Coloured socks to be cool, just a flash visible in otherwise smart monochrome.

Two pairs of socks to be toasty.

ScoutOfTheSoftHeartsClub · 04/03/2026 09:31

Meant to add - MH seems to offer a much smaller range of socks now. 🤷‍♀️

Gettingbysomehow · 04/03/2026 09:35

Im just watching Louise Minchin on this morning and she's wearing a long frilly dress in a mumsy print with white trainers and huge owl glasses.
She looks lkke something put of the Chums catalogue. Awful. Who styles these presenters.

Bimmering · 04/03/2026 10:33

myladyjane · 04/03/2026 08:46

So can I ask re the tights thing. I am just awaiting delivery of a denim shirt dress https://www.marksandspencer.com/pure-cotton-denim-midi-shirt-dress/p/clp60778348?color=DENIM&extid=ps_ps-pla-pmax_ggl_ww_ch__-UK-_-_bau&cq_src=google_ads&cq_cmp=20011577753&cq_con=&cq_term=&cq_med=pla&cq_plac=&cq_net=x&cq_plt=gp&gclsrc=aw.ds&gad_source=1&gad_campaignid=20014443268&gbraid=0AAAAAD7g6bRph44XNy-w8pYnpDy-Hdlxd&gclid=EAIaIQobChMIpaXbq-yFkwMV7ZRQBh3hmzNKEAQYAiABEgJyJfD_BwE

i have some green pointed flats, some tan ones, some chunky snakeskin loafers, some black knee high boots, some tan knee high flat boots and some ankle boots. Also many many trainers. In the summer I’d be ok with the flats and bare legs. In the cold I’d be ok with the knee high boots and some tights. But in the spring, what do I wear between the shoes and the dress? That’s the bit I get stuck on.

I just wear tights with flats? But I hate wearing shoes without tights or socks so I only do bare legs with sandals

DuckonaBike · 04/03/2026 18:31

I also find that finding the right tights is bigger challenge than finding the right shoes, once it’s too mild for boots and opaques.

There are quite a lot of patterned / lacy / micronet tights around which I’ve been experimenting with. I think they work well with a longer skirt when you’re only showing a little bit of tight.

I’m 53 if that’s relevant.

ChiliFiend · 04/03/2026 18:50

HummingBird50 · 04/03/2026 07:49

I saw a woman wearing low-heeled brogues and a dress, looked stunning. Am trying to find some as I will defo invest for spring/autumn. Boots for winter and sandals for summer with my dresses. I do prefer a heel though, even though I'm quite tall.

So I do I (prefer a heel). I don't care if it reveals me to be a millennial; you can see that from my face :) I just like the way it makes my legs look.

BoudiccaRuled · 04/03/2026 19:10

Carpedimum · 01/03/2026 18:08

I was at a meeting in London last week and was very surprised to see how many young women were wearing heels with trousers, skirts & dresses. There were court shoe style, Mary-Jane’s, pointy toe stilettos and kitten heels. There was a middle aged woman in a dress with trainers and by comparison, she looked frumpy and too casual because heels do change gait and trainers just don’t look formal or smart. I was even surprised by my own noticing of everyone’s outfits. I wear trainers to dash about in and I changed to low heels at the venue because I feel more put together in shoes, plus the venue has a dress code after 5pm. I hope we’ve truly reached an anything goes era.

An anything goes era as long as you don't mind feeling frumpy 🤣 The era of the "smart" trainer is coming to an end. Just a consequence of the memory of COVID casual fading, thank goodness.

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