20 Skirt-and-Boots Combinations to Wear All Winter Long

Once December hit, you probably packed away all of your favorite shorts and skirts so they could ride out winter in your closet. But skirts can stay in rotation as long you know the tricks of the trade. The key is to opt for warmer fabrics and pair them with tall boots. And aim for skirts that at least graze your knees. (Save those micro minis for summer.) Although pairing midi and maxi skirts with tall boots is a no-brainer, deciphering which boot goes with which skirt for ultimate warmth and sartorial points is a bit more complicated. You definitely want to try to cover up your legs so the top of the boot shaft either touches or goes under the hem of your skirt of choice. If your skirt has a slit, the boots should rise to the occasion. Found a pair that perfectly matches a skirt but leaves a little leg exposed to the harsh winter winds? That’s where tights come in handy. We went ahead and put together 20 skirt and boot pairings that’ll have you covered this winter.

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2020 Skirt and Boot Combos Update

Combo #1

Zara Geometric Print Midi Skirt, $69.90 at Zara
Combo #1

Mango Chain Detail Leather Boot, $229.99 at Mango
Combo #2

Mango Polka Dots Midi Skirt, $39.99 at Mango
Combo #2

Topshop Tambi Leather Natural Knee High Boots, $230 at Topshop
Combo #3

Universal Standard Ana Ribbed Sweater Skirt With Pocket in Powder Blue, $145 at Universal Standard
Combo #3

Universal Standard Lisbon Tall Boot in Black, $280 at Universal Standard
Combo #4

Farrow Ange Floral Skirt, $29 at Need Supply Co.
Combo #4

Isabel Marant Denvee Suede Knee Boots, $875 at Net-a-Porter
Combo #5

& Other Stories Belted Leather Midi Skirt, $349 at & Other Stories
Combo #5

Ulla Johnson Jerri Boots, $507 at Shopbop
Combo #6

Nanushka Seda Open Knit A-Line Skirt, $212 at Nanushka
Combo #6

Franco Shannon Boot in Putty Croco Print Leather, $159.99 at Franco Sarto
Combo #7

Which We Want Karina Maxi Skirt, $29 at Need Supply Co.
Combo #7

& Other Stories Suede Thigh High Cowboy Boots, $349 at & Other Stories
Combo #8

Erdem Elvin Poppy-Print Midi Skirt, $695 at Matches Fashion
Combo #8

Petar Petrov Soekie Leather Knee-High Boots, $622 at mytheresa.com
Combo #9

Dries Van Noten Intarsia Wool and Alpaca-Blend Skirt, $318 at mytheresa.com
Combo #9

Mango Leather High-Leg Boots, $199.99 at Mango
Combo #10

J.Crew Velvet Pull-On Skirt in Academic Green, $110 at J.Crew
Combo #10

Atelier by Vagabond Alison Tall Boot in Black, $325 at Need Supply Co.
Combo #11

Sacai Blanket Skirt, $430 at La Garçonne
Combo #11

Steve Madden Triumph Boot, $150 at Revolve
Combo #12

Versace Printed Stretch-Jersey Skirt, $795 at Net-a-Porter
Combo #12

The Frankie Shop Lug Sole Tall Boots in Black, $395 at The Frankie Shop
Combo #13

Mango Checked Midi Skirt, $79.99 at Mango
Combo #13

Zara High Leg Leather Heeled Boots, $79.99 at Zara
Combo #14

The Frankie Shop Copper Brown Single Pocket Slit Skirt, $125 at The Frankie Shop
Combo #14

Madewell Greta Tall Western Boots, $208.60 at Shopbop
Combo #15

Victoria, Victoria Beckham Striped Ribbed-Knit Midi Skirt, $305 at Net-a-Porter
Combo #15

Jacquemus Les Bottes Leon Hautes Boots, $566.40 at Shopbop
Combo #16

Reformation Zander Skirt in Formosa, $88 at Reformation
Combo #16

ALDO Maddalena, $99.98 at ALDO
Combo #17

Hope for Flowers by Tracy Reese Poppy Pencil Skirt, $220 at Anthropologie
Combo #17

Tamara Mellon Combat Mid Calf, $695 at Tamara Mellon
Combo #18

Zimmermann Super Eight Leaf-Print Linen Midi Skirt, $590 at Matches Fashion
Combo #18

Urban Outfitters Boo Knee-High Boot, $110 at Urban Outfitters
Combo #19

Batsheva Ruffled Floral-Print Cotton Midi Skirt, $248 at Matches Fashion
Combo #19

Marni Pant Boot in Mirrored Silver Calf, $556 at Totokaelo
Combo #20

& Other Stories Crocodile Print Midi Skirt, $79 at & Other Stories
Combo #20

Clergerie Xareni Tall Boots, $340 at La Garçonne