If there’s one clear message from this fashion month, it’s that 2027 will be the year of the skirt. Miuccia Prada and Raf Simons have asked us to set aside trousers and dresses for the time being—the spring/summer 2027 Prada collection featured 63 looks, all built around a skirt. What Miuccia says always matters, and the street style crowd is already following her no-trousers lead.

Our Favorite Pencil Skirt and Pump Combos:

The Floral Jacquard
Zara floral midi skirt
$70 ZARA

The White Pump
Jude Blade 60 leather pumps
$570 NET-A-PORTER

The Pleated Midi
Pleats Please Issey Miyake pleated midi skirt
$395 NORDSTROM

The Buckled Style
Tory Burch slingback leather heels
$475 SHOPBOP

The Fringe Trim
Róhe double-faced fringe skirt
$905 RÓHE

The Croc Effect
Reformation Calista slingback heels
$278 SHOPBOP

The Pony Hair Midi
Nour Hammour Elyse midi skirt
$1,590 NET-A-PORTER

The Snakeskin Pop
Jamie Haller The Trap pumps
$740 SHOPBOP

Although the street style galleries show many different skirt trends, from fall florals to bold-colored midis, if we had to name one outfit as the uniform of the spring/summer 2027 show circuit, it would be a column pencil skirt paired with pointed pumps.

Vincenzo Grillo

You might think a suit skirt and court shoes sound a bit like something from The Apprentice, but the styling here has a softness that keeps it from feeling too severe or corporate. Jeanne Damas, for example, wore black glossy slingbacks with a black tailored skirt, giving a polished base to her otherwise relaxed weekend staples (she wore a shirt with rolled-up sleeves under a striped jumper, plus aviators).

Daniel Zuchnik/Getty Images
Vincenzo Grillo

Labels like Bottega Veneta, The Row, and Prada have modernized the pencil skirt for 2026, moving away from rigid, tight fits toward a more relaxed silhouette that fits the current soft power styling mood. Traditional suiting is loosened with oversized silhouettes, fluid fabrics, and styling that feels elevated but never too formal. Pointed-toe pumps might suggest you’re an inbox-zero, black-coffee-with-an-extra-shot kind of person, but adding a T-shirt, bomber jacket, or track jacket brings some Type B energy and makes it look a little less 5 a.m. club.

Vincenzo Grillo
Vincenzo Grillo

To make your pencil skirt look more street style in 2026, swap a blazer for a bomber, a laptop bag for a neat top-handle bag, and a silk blouse for a crew-neck jumper. Keep scrolling to shop the skirt and shoe pairing that was the uniform this fashion month.

Day-to-Night Polish
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Róhe wool padded coat
$1,740 RÓHE
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Jil Sander strapless bustier top
$1,490 NET-A-PORTER
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Zara floral midi skirt
$70 ZARA
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Jude Blade 60 leather pumps
$570 NET-A-PORTER

The Bold Color Combo
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J.Crew cashmere crewneck sweater
$198 J.CREW
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Zara ribbed T-shirt
$30 ZARA
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Róhe double-faced fringe skirt
$905 RÓHE
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Reformation Calista slingback heels
$278 SHOPBOP

Preppy Minimalism
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Guest in Residence collegiate striped sweater
$445 NET-A-PORTER
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Arma Paula jacket
$1,395 SHOPBOP
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Pleats Please Issey Miyake pleated midi skirt
$395 NORDSTROM
$495 NET-A-PORTER
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Tory Burch slingback leather heels
$475 SHOPBOP

Considered Texture
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Reiss V-neck jumper
$248 REISS
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Blue Nile squared bangle
$3,685 BLUE NILE
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Nour Hammour Elyse midi skirt
$1,590 NET-A-PORTER
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Jamie Haller The Trap pumps
$740 SHOPBOP
$740 NET-A-PORTER

Sport Mode
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Nike Nike One jacket
$75 NIKE
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Still Here
Daughter polo shirt
$195 NET-A-PORTER
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Cos
Checked midi skirt
$159 COS
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Khaite
Valerie low pumps
$990 KHAITE
Dealing in Opposites
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Emily Dawn Long
Jeff’s button-up shirt
$375 EMILY DAWN LONG
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Coach
Brooklyn shoulder bag
$395 COACH
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Another Tomorrow
Eyelet skirt
$750 ANOTHER TOMORROW
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Aeyde
Cari suede pumps
$545 NET-A-PORTER
Classic With a Twist
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& Other Stories
Relaxed trench coat
$259 & OTHER STORIES
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The Park
Dina jersey T-shirt
$165 NET-A-PORTER
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J.Crew
A-line skirt
$298 J.CREW
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Prada
Embroidered slingback pumps
$2,050 PRADA

Frequently Asked Questions
FAQs The Shoe and Skirt Combo Taking Over Street Style This Month

1 What is the shoe and skirt combo everyones talking about
Its a styling trend where skirts are paired with unexpected shoes mainly ballet flats chunky sneakers and kneehigh boots instead of the usual heels or sandals

2 Why is this combo suddenly everywhere
Its comfortable easy to pull off and looks effortlessly stylish Fashion influencers and street style stars started wearing it and it spread fast on social media

3 Which shoes work best with midi skirts
Ballet flats loafers and pointedtoe kitten heels For a cooler look try chunky sneakers or ankle boots

4 Can I wear sneakers with a long skirt
Yes Chunky or retro sneakers with a maxi or midi skirt is one of the biggest versions of this trend Just keep the skirt flowy and the sneakers clean

5 Whats the easiest version for a beginner
A midi skirt with white sneakers Its foolproof comfortable and works for almost any occasion

6 Does this combo work for office wear
Absolutely A pencil or Aline skirt with loafers or low heels looks polished and professional

7 How do I stop the combo from looking frumpy
Balance proportions if the skirt is long and loose go for a sleeker shoe If the skirt is short or fitted you can go chunkier Also show a bit of ankle or leg where you can

8 What shoes should I avoid with mini skirts
Very chunky platforms or heavy combat boots can overwhelm a mini skirt Stick to ballet flats low sneakers or slim boots for balance

9 Which shoe colors go with any skirt
Nude black white and tan They match almost everything and keep the outfit looking intentional

10 Can I wear this combo in cold weather
Yes pair a midi skirt with kneehigh boots tights and a cozy sweater Its one of the best coldweather street style looks

11 How do I make my legs look longer with this combo
Match your shoe color to your skin tone or tights and pick a skirt that hits at or above the knee Pointed toes also help