How to style midi skirts this Fall/Winter

Move over maxi skirts, midi skirts are shaping up to be the trending length for Fall/Winter 2023! Versatile, season-appropriate, and super chic, midi skirts are an absolute staple in our wardrobes. Ranging in length from right below the knee to just above the ankles, it’s guaranteed that the right midi skirt for your proportions is out there somewhere!

Hailey Bieber is seen wearing black sunglasses, an ankle-length black coat, a black bra top, a black midi skirt, and black leather boots.

Getty Images

Looking for inspo? We’ve got you covered. Here are 6 it-girl-approved ways to style your midi skirts this Fall/Winter.

1. Total black with a black denim skirt

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You can never go wrong with a total black look! We love how Felicity Bird styled her midi black denim skirt with a black boxy jumper, black knee-high boots, and black accessories. Dark-wash denim is the way to go for a chic yet effortless look.

-41%

AllSaints

Womens Merino Wool Myra Cowl Neck Merino Wool Jumper, Size: XS Black

Delivery: free

£81.90 ~~£139.00~~

AllSaints

Serena Bute

Merino Wool Relaxed Fit Jumper - Black

Delivery: £5.95

£175.00

Serena Bute

Givenchy

Black Distressed Knitted Oversize Logo Jumper Size XS

Delivery: £5.00

£201.60

HEWI

-25%

Tommy Hilfiger

Relaxed V-Neck Jumper With Cashmere Grey

Delivery: £4.90

£187.00 ~~£250.00~~

Tommy Hilfiger

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-60%

Isabel Marant

Vandy high-rise denim midi skirt Black

Delivery: Delivery costs apply

£138.00 ~~£345.00~~

Mytheresa

-35%

Versace Jeans Couture

Midi Skirts, female, Black, M, High-Waisted Midi Skirt

Delivery: Delivery costs apply

£220.55 ~~£339.30~~

Miinto

BESTSELLER

Christophe Lemaire

Asymmetric denim midi skirt Black

Delivery: Delivery costs apply

£370.00

Mytheresa

Versace Jeans Couture

Midi Skirts, female, Black, XS, Knit Midi Skirt

Delivery: Delivery costs apply

£399.08

Miinto

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-40%

AllSaints

Womens Cow Leather Avril Knee High Leather Boots, Size: UK 4/ US 7/ EU 37 Black

Delivery: free

£180.00 ~~£299.00~~

AllSaints

Charles & Keith

Yvette Metallic-Accent Knee-High Boots Black

Delivery: free

£109.00

Charles & Keith

AllSaints

Womens Cow Leather Maeve Leather Knee High Boots, Size: UK 7/US 10/EU 40 Black

Delivery: free

£299.00

AllSaints

Charles & Keith Robbie Cut-Out Knee-High Boots

-20%

BESTSELLER

Charles & Keith

Robbie Cut-Out Knee-High Boots Black

Delivery: free

£76.00 ~~£95.00~~

Charles & Keith

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2. A plaid skirt with tonal items

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We’re obsessed with the colour story in Annette Weber’s outfit! Her cream jumper and grey peacoat perfectly match the tartan print of her skirt, while her printed handbag clashes with oh-so-perfectly.

Mauro Grifoni

double-breasted wool jacket - Blue

At FARFETCH

£453.00 ~~£510.00~~

Delivery: free

Buy it here

Kocca

Delicate Chic Long Sleeve Close Neck Sweatshirt

At Miinto

£66.99 ~~£73.95~~

Delivery: Delivery costs apply

Buy it here

Maje

Checked cotton midi skirt - Blue - FR 34

At The Outnet

Sold out

3. Officecore vibes

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You heard it here first: Y2K Officecore will be the next viral -core to take social media by storm. To be ahead of the trend, style your pencil midi skirt with a silky white button-down, pointy kitten heels, and a slightly oversized blazer. Bonus points if you also have small rectangular metal-frame glasses.

Kocca Midi Skirts, female, Green, M, Chic Leather Look Pencil Skirt

-9%

BESTSELLER

Kocca

Midi Skirts, female, Green, M, Chic Leather Look Pencil Skirt

Delivery: Delivery costs apply

£76.56 ~~£84.39~~

Miinto

-58%

Prototypes

Poly Jersey Pencil Skirt Black

Delivery: Delivery costs apply

£165.00 ~~£395.00~~

Labels

Generic

Wool Plaid Pencil Skirt for Women UK Winter High Waist Slit Tight Knee Length Midi Skirt Checked Skirts Green

Delivery: Delivery costs apply

£13.99

Amazon

Veronica Beard Tanner kniited pencil skirt

-30%

BESTSELLER

Veronica Beard

Tanner kniited pencil skirt Black

Delivery: Delivery costs apply

£231.00 ~~£330.00~~

Mytheresa

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-50%

Ganni

Satin Peplum Tie Blouse - Size 34 White

Delivery: £5.00

£127.50 ~~£255.00~~

GANNI

-48%

Reiss

Tie-detail Shadow-stripe Blouse, 12 White

Delivery: Delivery costs apply

£98.00 ~~£190.00~~

Reiss

-46%

AllSaints

Polyester Leanne Satin Relaxed Top, Size: UK 6/US 2 White

Delivery: free

£53.10 ~~£99.00~~

AllSaints

-66%

Reiss

Cream | Royal Ballet Tie-cuff Blouse, 10 White

Delivery: Delivery costs apply

£68.00 ~~£198.00~~

Reiss

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Theory

Pencil Skirt in Stretch Wool Black

Sold out

£155.00

Theory

Debenhams

Midi Pencil Skirt Black

Sold out

£39.20

Debenhams

Reiss

Haisley Pencil Skirt Wool Plain, Navy Size: 12 Blue

Sold out

£118.00

Reiss

Joseph

Silk Stretch Pencil Skirt Black

Sold out

£275.00

JOSEPH

Charles & Keith

Cody Leather Pointed-Toe Kitten-Heel Slingback Pumps Black

Delivery: free

£95.00

Charles & Keith

Luciana Patent Slingback Kitten Heels Red

Delivery: £4.00

£59.00

Charles & Keith

-20%

Charles & Keith

Sequin Mesh & Leather Slingback Kitten Heels Silver

Delivery: £4.00

£71.00 ~~£89.00~~

Charles & Keith

-40%

Charles & Keith

Raffia Pointed-Toe Slingback Pumps Orange

Delivery: £4.00

£39.00 ~~£65.00~~

Charles & Keith

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4. A blue denim skirt and red accents

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Red accents are huge this season; one of the most effortless ways to add a pop of colour to your look is to wear your blue denim midi skirt with a red cardigan, and even red socks.

-50%

Ganni

Red Burgundy Check Cardigan - Size XS Merino Wool

Delivery: free

£182.50 ~~£365.00~~

GANNI

-10%

Vero Moda

Bordeaux Knit Cardigan Fall/Winter Red

Delivery: Delivery costs apply

£67.51 ~~£74.99~~

Miinto

Polo Ralph Lauren

Cable-knit wool and cashmere cardigan Red

Delivery: Delivery costs apply

£245.00

Mytheresa

Missoni

M Missoni Stretch Knit Cardigan Size M Red

Delivery: £5.00

£169.00

HEWI

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Khaite

Maggie Denim Midi Skirt Size 27/69 Blue

Delivery: £5.00

£179.00

HEWI

-30%

Veronica Beard

Alix denim midi skirt Blue

Delivery: Delivery costs apply

£231.00 ~~£330.00~~

Mytheresa

-30%

BA&SH

Laddie button-front denim midi skirt - Blue

Delivery: £10.00

£144.00 ~~£205.00~~

FARFETCH

-50%

Veronica Beard

Victoria denim midi skirt Blue

Delivery: Delivery costs apply

£130.00 ~~£260.00~~

Mytheresa

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5. Neutral shades

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Sometimes you just feel like taking it back to the basics, and we can’t blame you! A black column midi skirt with a white t-shirt, a relaxed grey sweater, and brown pointed boots are minimalist perfection.

Style tip: when styling tall boots, go for a longer midi skirt so that it slightly covers the top of the boots. This will make sure you don’t fall into the trap of the “skin sandwich”—that little slice of exposed skin between the hem of the skirt and the top of the boot—that breaks up the flow of your outfit.

-10%

Closed

Round-neck Knitwear, female, Gray, M, Light Grey Wool Crew Neck Jumper

Delivery: Delivery costs apply

£187.92 ~~£208.80~~

Miinto

-40%

AllSaints

Wool Bern V-Neck Wool Jumper, Size: XS White

Delivery: free

£83.70 ~~£139.00~~

AllSaints

Tommy Hilfiger

Logo Embroidery Terry Quarter-Zip Jumper Orange

Delivery: £4.90

£120.00

Tommy Hilfiger

-40%

AllSaints

Polyamide/Wool Clyde Funnel Neck Jumper, Size: XS Grey

Delivery: free

£107.10 ~~£179.00~~

AllSaints

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-50%

adidas Originals

Satin Skirt Black

Delivery: Delivery costs apply

£125.00 ~~£250.00~~

Labels

-30%

Fat Face

FatFace Annie Black Lace Midi Skirt

Delivery: £4.95

£48.00 ~~£69.00~~

FatFace

-52%

Adnym Atelier

Lach Kilt Black

Delivery: Delivery costs apply

£190.00 ~~£395.00~~

Labels

Fat Face

FatFace Harper Black Layered Animal Midi Skirt

Delivery: £4.95

£59.00

FatFace

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-40%

AllSaints

Leather Odyssey Knee High Suede Boots, Size: UK 4/ US 7/ EU 37 Brown

Delivery: free

£209.70 ~~£349.00~~

AllSaints

BESTSELLER

Charles & Keith

Lyndon Buckled Knee-High Boots Brown

Delivery: free

£109.00

Charles & Keith

-23%

Windsor Smith

Windsorsmith Womens Oak Brown Faux Leather Knee-High Platform Heel Boots - Niche - Size UK 8

Delivery: £2.99

£119.99 ~~£154.99~~

Secret Sales

Charles & Keith

Faux Suede Tie-Around Knee-High Boots Red

Delivery: free

£109.00

Charles & Keith

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6. With a funnel neck jumper and sneakers

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Layering during the colder months is fundamental, and so is being able to style your clothes for all seasons to get the most wear out of them. Here Dominika shares how to take your midi skirt + sneakers combo from Spring/Summer to Fall/Winter by adding a funnel neck sweater, tights, socks, and a quilted jacket.