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.
[ Next: 10 Street Style-Approved Ways to Dress Up a Sweatshirt ]
2020 Skirt and Boot Combos Update
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Combo #1
Zara Geometric Print Midi Skirt, $69.90 at Zara
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Combo #1
Mango Chain Detail Leather Boot, $229.99 at Mango
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Combo #2
Mango Polka Dots Midi Skirt, $39.99 at Mango
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Combo #2
Topshop Tambi Leather Natural Knee High Boots, $230 at Topshop
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Combo #3
Universal Standard Ana Ribbed Sweater Skirt With Pocket in Powder Blue, $145 at Universal Standard
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Combo #3
Universal Standard Lisbon Tall Boot in Black, $280 at Universal Standard
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Combo #4
Farrow Ange Floral Skirt, $29 at Need Supply Co.
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Combo #4
Isabel Marant Denvee Suede Knee Boots, $875 at Net-a-Porter
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Combo #5
& Other Stories Belted Leather Midi Skirt, $349 at & Other Stories
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Combo #5
Ulla Johnson Jerri Boots, $507 at Shopbop
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Combo #6
Nanushka Seda Open Knit A-Line Skirt, $212 at Nanushka
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Combo #6
Franco Shannon Boot in Putty Croco Print Leather, $159.99 at Franco Sarto
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Combo #7
Which We Want Karina Maxi Skirt, $29 at Need Supply Co.
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Combo #7
& Other Stories Suede Thigh High Cowboy Boots, $349 at & Other Stories
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Combo #8
Erdem Elvin Poppy-Print Midi Skirt, $695 at Matches Fashion
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Combo #8
Petar Petrov Soekie Leather Knee-High Boots, $622 at mytheresa.com
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Combo #9
Dries Van Noten Intarsia Wool and Alpaca-Blend Skirt, $318 at mytheresa.com
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Combo #9
Mango Leather High-Leg Boots, $199.99 at Mango
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Combo #10
J.Crew Velvet Pull-On Skirt in Academic Green, $110 at J.Crew
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Combo #10
Atelier by Vagabond Alison Tall Boot in Black, $325 at Need Supply Co.
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Combo #11
Sacai Blanket Skirt, $430 at La Garçonne
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Combo #11
Steve Madden Triumph Boot, $150 at Revolve
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Combo #12
Versace Printed Stretch-Jersey Skirt, $795 at Net-a-Porter
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Combo #12
The Frankie Shop Lug Sole Tall Boots in Black, $395 at The Frankie Shop
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Combo #13
Mango Checked Midi Skirt, $79.99 at Mango
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Combo #13
Zara High Leg Leather Heeled Boots, $79.99 at Zara
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Combo #14
The Frankie Shop Copper Brown Single Pocket Slit Skirt, $125 at The Frankie Shop
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Combo #14
Madewell Greta Tall Western Boots, $208.60 at Shopbop
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Combo #15
Victoria, Victoria Beckham Striped Ribbed-Knit Midi Skirt, $305 at Net-a-Porter
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Combo #15
Jacquemus Les Bottes Leon Hautes Boots, $566.40 at Shopbop
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Combo #16
Reformation Zander Skirt in Formosa, $88 at Reformation
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Combo #16
ALDO Maddalena, $99.98 at ALDO
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Combo #17
Hope for Flowers by Tracy Reese Poppy Pencil Skirt, $220 at Anthropologie
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Combo #17
Tamara Mellon Combat Mid Calf, $695 at Tamara Mellon
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Combo #18
Zimmermann Super Eight Leaf-Print Linen Midi Skirt, $590 at Matches Fashion
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Combo #18
Urban Outfitters Boo Knee-High Boot, $110 at Urban Outfitters
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Combo #19
Batsheva Ruffled Floral-Print Cotton Midi Skirt, $248 at Matches Fashion
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Combo #19
Marni Pant Boot in Mirrored Silver Calf, $556 at Totokaelo
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Combo #20
& Other Stories Crocodile Print Midi Skirt, $79 at & Other Stories
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Combo #20
Clergerie Xareni Tall Boots, $340 at La Garçonne
