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.

-48%

AllSaints

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

Delivery: free

£72.80 ~~£139.00~~

AllSaints

-17%

Roman

Fairisle Knit Jumper Dress Black

Delivery: free

£40.00 ~~£48.00~~

Roman

BESTSELLER

Liu Jo

high-neck ruffle-detail sweater - Black

Delivery: £10.00

£185.00

FARFETCH

-28%

Roman

Faux Pearl Contrast Cable Knit Jumper Black

Delivery: free

£26.00 ~~£36.00~~

Roman

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-60%

Isabel Marant

Vandy high-rise denim midi skirt Black

Delivery: Delivery costs apply

£138.00 ~~£345.00~~

Mytheresa

-25%

Roman

Front Split Knitted Midi Skirt Black

Delivery: free

£24.00 ~~£32.00~~

Roman

-36%

Ground-Zero

panelled denim midi skirt - Black

Delivery: £10.00

£89.00 ~~£138.00~~

FARFETCH

-14%

Musium Div.

patchwork frayed-hem denim midi skirt - Black

Delivery: £10.00

£107.00 ~~£125.00~~

FARFETCH

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Charles & Keith

Sasky Knee High Flat Boots Black

Delivery: free

£105.00

Charles & Keith

-47%

Dune London

Womens Ladies TRUSTI Casual Knee-High Boots - Black Leather (archived) - Size UK 4

Delivery: £2.99

£84.98 ~~£159.99~~

Secret Sales

Charles & Keith

Faux Suede Fold-Over Back-Tie Thigh-High Boots Black

Delivery: free

£99.00

Charles & Keith

-60%

Dune London

Womens Ladies TRUCE 2 Ruched Block Heeled Knee High Boots 2 - Black Leather (archived) - Size UK 7

Delivery: £2.99

£64.00 ~~£160.00~~

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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.

Wallis

Womens Petite Double Breasted Pea Coat - Navy - Size 16 UK

At Secret Sales

£66.50 ~~£95.00~~

Delivery: £2.99

Buy it here

AllSaints

Merino Wool Julieana V Neck Wool Jumper, Size: XS

At AllSaints

£56.00 ~~£139.00~~

Delivery: free

Buy it here

Maje

BOTTOMWEAR - Midi skirts on YOOX.COM

At Yoox.com

£101.00 ~~£182.00~~

Delivery: £9.00

Buy it here

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.

Veronica Beard Tanner kniited pencil skirt

-30%

BESTSELLER

Veronica Beard

Tanner kniited pencil skirt Black

Delivery: Delivery costs apply

£231.00 ~~£330.00~~

Mytheresa

Generic

Unbranded New Women Printed Midi Bodycon Pencil Skirt Ladies High Waist Tube Skirt Fancy Dress (L/XL (UK 16-18), Green Tartan)

Delivery: Delivery costs apply

£6.49

Amazon

-20%

BESTSELLER

Norma Kamali

Faux leather pencil skirt Black

Delivery: Delivery costs apply

£124.00 ~~£155.00~~

Mytheresa

HUGO BOSS Womens Freedah Knitted Pencil Skirt in Brown Viscose - Size 12 UK

-70%

BESTSELLER

HUGO BOSS

Womens Freedah Knitted Pencil Skirt in Brown Viscose - Size 12 UK

Delivery: £2.99

£59.99 ~~£198.99~~

Secret Sales

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-60%

L.k. Bennett

Womens TW ELSIE POLKA DOT BLOUSE, White/Navy - Size 16 UK

Delivery: £2.99

£79.00 ~~£199.00~~

Secret Sales

-52%

AllSaints

Polyester Leanne Satin Relaxed Top, Size: UK 14/US 10 White

Delivery: free

£47.20 ~~£99.00~~

AllSaints

-50%

Serena Bute

Satin Cargo Shirt - Cream White

Delivery: £5.95

£163.00 ~~£325.00~~

Serena Bute

-44%

BESTSELLER

Forte_Forte

TOPWEAR - Tops on YOOX.COM White

Delivery: £9.00

£114.00 ~~£205.00~~

Yoox.com

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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

-15%

BESTSELLER

Michael Michael Kors

logo-plaque cut-out pumps - Black

Delivery: £10.00

£174.00 ~~£205.00~~

FARFETCH

Charles & Keith

Curtis Patent Pointed-Toe Kitten Heel Pumps Black

Delivery: £4.00

£65.00

Charles & Keith

-13%

BESTSELLER

Bibi Lou

FOOTWEAR - Pumps on YOOX.COM Brown

Delivery: £9.00

£110.00 ~~£126.00~~

Yoox.com

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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%

Self Portrait

Embellished cardigan Red

Delivery: Delivery costs apply

£190.00 ~~£380.00~~

Mytheresa

Polo Ralph Lauren

cable-knit cardigan - Red

Delivery: £10.00

£225.00

FARFETCH

Roman

Open Knitted Cardigan Red

Delivery: free

£28.00

Roman

-30%

Simone Rocha

Bow-detail open-knit wool-blend cardigan Red

Delivery: Delivery costs apply

£245.00 ~~£350.00~~

Mytheresa

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Levi's

back-slit denim midi skirt - Blue

Delivery: £10.00

£86.00

FARFETCH

-30%

Veronica Beard

Alix denim midi skirt Blue

Delivery: Delivery costs apply

£231.00 ~~£330.00~~

Mytheresa

-10%

American Vintage

denim midi skirt - Blue

Delivery: £10.00

£131.00 ~~£146.00~~

FARFETCH

Roman

Mixed Floral Spot Print A Line Midi Skirt Blue

Delivery: free

£32.00

Roman

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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.

-22%

Roman

Diamond Sparkly Knit Jumper Grey

Delivery: free

£28.00 ~~£36.00~~

Roman

Polo Ralph Lauren

Polo Bear cotton-blend fleece sweatshirt Grey

Delivery: Delivery costs apply

£235.00

Mytheresa

Roman

Nordic Print Button Detail V-Neck Jumper Grey

Delivery: free

£40.00

Roman

-60%

AllSaints

Merino Wool Julieana V Neck Wool Jumper, Size: XS White

Delivery: free

£56.00 ~~£139.00~~

AllSaints

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-40%

Isabel Marant

Angele faux leather midi skirt Black

Delivery: Delivery costs apply

£237.00 ~~£395.00~~

Mytheresa

Fat Face

FatFace Harper Black Midi Skirt

Delivery: £4.95

£59.00

FatFace

-30%

Frankie Shop

Gabrielle knitted midi skirt Black

Delivery: Delivery costs apply

£161.00 ~~£230.00~~

Mytheresa

BESTSELLER

AllSaints

Annalie asymmetric midi skirt - Black

Delivery: £10.00

£132.00

FARFETCH

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Charles & Keith

Faux Suede Tie-Around Knee-High Boots Red

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

-40%

Charles & Keith

Masei Faux Suede Grommet-Strap Knee-High Boots Brown

Delivery: £4.00

£71.40 ~~£119.00~~

Charles & Keith

-51%

Dune London

Womens Ladies Tepi - Buckle-Detail Casual Knee-High Boots - Tan Leather (archived) - Size UK 3 Brown

Delivery: £2.99

£71.00 ~~£145.00~~

Secret Sales

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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.