Update my pencil skirts please

[TotallyFloored]

So the last time I was in the office it was all pencil skirts, killer heels etc…

I have loads in my wardrobe - is there any way to update these so I can get some wear out of them ?

Pencil skirts are pretty classic, and some workplaces are more formal than others but I'd say it's mort important what you wear on top and what shoes.

I have one I still wear only in winter with boots and a big jumper. I can just get away with it but it does date me. I only bother becasue its beautiful wool. If they're polyester blends just say goodbye. More than anything else at this point they do age us, and while we should not care, that we are on this board suggests that we do ....

I’m waiting for a leather pencil skirt to be delivered from Vinted, which may or may not be knee-length on. I’m going to wear it with chunky soled lower-calf boots (slightly paratrooper), crisp boxy t-shirt tucked in, and maybe an oversized very boxy vintage blazer with shoulder pads (love the blazer but not yet figured out what to wear it with…)
I might wear it with an excessively fluffy pastel angora jumper, or with an oversized lurex jumper with a belt. I’ll definitely wear it to work with vintage 80s-ish not-fitted silk (or poly…) blouses.
I’m a bold dresser but get compliments on elegance too, promise I don’t look like a clown!

I will - thanks!

I always think shoes are a big predictor of what’s to come fashion wise, mainly because they take longer and are harder to mass produce. I think kitten heels, pointy flats and ballet pumps all lend themselves to pencil skirts, that whole 50’s look (pedal pushers seem to have turned up again) so maybe they are going to be the next big thing!

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29 Dec 2025

I love pencil skirts but I can't wear them anymore because of my tummy pouch that I can't get rid of!
I used to wear plain coloured skirts with pretty blousy tops, or casual knit tops, either plain black (to tone down the brightness of my outfit) or different prints and designs.
I always felt like I was sashaying through a fashion parade in my work clothes

I have to agree with this. While I'm not one to be suckered into the latest trends I occasionally see this look in town - the pencil skirt, the see through black tights, the heels 😬 It's like a flashback to the 1980s.

I have a few pencil skirts I really love- all a few inches below the knee. As an hourglass I would think twice about pairing with anything boxy, as I have hips and wide shoulders, so would look wide all the way down. Maybe something really slouchy though ( molly ringwald style as someone mentioned).
Personally, if I am the mood for a pencil skirt for work I wear it with a fitted top and chunky heels. My lovely 20 something colleagues always tell me they love my grown up outfits but don’t have the confidence to wear them 🙂While they are possibly humouring the mad old bat, I don’t really care. I’m not trying to not look my age, I’m just wearing beautiful clothes I feel good in and by our 40’s we should have the confidence to eschew trends and concentrate on the joy of having wardrobes that span decades!

Kate Moss at a recent show

Saint Laurent as a brand does tend to live in the past …

I work in an office (nhs trust) and NOBODY wears ridiculous heels, even our managers wear flats/loafers.
Mrs pencil skirts - some people wear them mainly plain black ones with a top but if you’re happy with them then wear them.
I have to get 3 kids out the door and sorted before I even leave so I’m not remotely bothered about looking “current” I go for smart and well presented I buy afew new bits here and there but tend to stick to smart trousers and a top really.

Kate Moss is an icon so if it’s good enough for her…

I agree re a fitted top to compliment the skirt vs something more boxy. I mainly WFH and for my occasional trips to my company’s London HQ I tend to lean towards workwear style dresses rather than separates. In the past when I was more office based and did wear pencil skirts, I always paired them with a fitted top. I have an hourglass figure like the OP, so tended to find a boat neck style, similar to something like this, worked well.

www.johnlewis.com/boden-essential-boat-neck-jersey-top/white/p110766313

When I go into the office (admittedly only once per month on average), I always wear heels. The trip involves a train to London and tube travel so the commute I’ll do in ballet pumps, but will change into my high heels when I get to the building.

Sadly, at 44 and mainly thanks to default slipper/slider wearing during Covid lockdowns and 7 years spent as a home based worker, long gone are the days of my calf muscles and achilles tendons joyously embracing the prospect of spending entire days traversing the City in 5 inch stiletto heels, without fear of cramps, muscle spasms, back pain or blisters. The mere thought of that now is making my toes curl! 😂

None of us wear heels I think if someone turned up in them we’d all be shocked!!!!

Conway could I stand up in them all day not a chance! All my heels have gone on vinted 🤣 I’m definately not into uncomfortable shoes these days!

🤣🤣 I think after almost exclusively wearing high heels from my teens, well into my 30s, I’d essentially deadened my feet to any sense of feeling, so could easily spend all day on them. In fact, my body was so conditioned to heels, my calf muscles became shortened to the extent I struggled to keep my heel flat to the floor without them really aching. Madness!! 😂

I take back what I said - COS have a selection of pencil skirts in for Spring.

https://www.cos.com/en-gb/search?search=pencil+skirt

I like quite a few of the Cos skirts, and the Frankie shop ones too - thanks both for the links - but only a couple of them match my mental image of a pencil skirt, which is very fitted around the arse, tapering a little towards the hem and finishing on or just below the knee. Most of them are too A-line, too straight-up-and-down or too long to fit the description, in my personal and very fussy opinion.

Mine were the same. Actually struggled in flats so I’m not sure I owned any. Went into the delivery suite of hospital in 5” heels.
I still occasionally wear them now as I’m very short so need them to stop me looking dumpy!!

I’ve noticed some of the girls at school pick up are starting to wear the chunky 90’s ones.

Below knees or mid calf / longer are def lurking ready to emerge. I wouldn’t go on knee length ghough. Search pencil skirt on insta and there are plenty of more modern looks to be inspired by

I'd recommend scrolling through these pages to get a sense of styling. There are a variety of skirts, some pencil ones. Most are longer than knee length, but some are at the knee. I noticed the other day that The Attico are doing a fishtail type skirt.

https://www.net-a-porter.com/en-gb/shop/clothing/skirts/midi-skirts?orderBy=10&pageNumber=1

Why don’t you have them taken up to a regular skirt/mini? I have no dressmaking experience but assume this is possible, and after a recent alteration couldn’t believe how cheap it is.

It’s the length rather than the shape op thay makes them dated. Midi is current right now. Anything knee length is very dated, also skirts tend to the loose now, where as pencil tend to be more form skimming,

you can wear them with slouchy jumpers or shirts, chunky boots, like you would a midi length one,but they will still look very dated and it maybe too casual for some offices.

of course you can wear what you want, no one needs to look current, but there is no way to make them look current and no one will be thinking well Kate moss wore one recently.