21 Stylish Skirts to Take You From Summer to Fall

21 Stylish Skirts to Take You From Summer to Fall
Style Du Monde

Skirts, which come in so many varying lengths, fabrics, colors, and patterns, are the perfect summer-to-fall transitional piece. They allow you to subtly shift your wardrobe for the upcoming season, without sacrificing comfort in still-sweltering temperatures. From anything-but-boring pencil skirts to flirty miniskirts, we’ve sourced the hottest styles to take you from the dog days of summer through harvest season.

Scroll down to shop our favorite summer-to-fall transitional skirts!

  • 1 of 21

    Zara Jacquard Miniskirt ($60) in Black

    Eyelash fringe is an adorable finishing touch on this tweed mini skirt.

  • 2 of 21

    J.Crew Pleated Chevron Skirt ($148) in Navy

    Tap into the pleated trend with this option, which comes in fall-friendly colors.

  • 3 of 21

    Topshop Quilted Leather Pencil Skirt ($200) in Black

    A chic leather skirt at this price point is a must-have.

  • 4 of 21

    10 Crosby Derek Lam Box Pleat Skirt ($395) in Nude

    This pale pink skirt transitions nicely into fall thanks to its structured silhouette.

  • 5 of 21

    NIC+ZOE Midnight Sky Midi Skirt ($118) in Black Mix

    This slim take on a ladylike midi skirt is ultra-flattering.

  • 6 of 21

    Thakoon Addition Fringed Knit Wool Skirt ($325)

    An asymmetrical fringe hem has major sartorial impact on this knit mini.

  • 7 of 21

    Elizabeth and James Raya Striped Zipper Skirt ($265)

    This miniskirt feels both ‘90s-inspired and modern. 

  • 8 of 21

    ASOS Premium Pencil Skirt in Bonded Satin ($97) in Purple

    Try this dressy pencil skirt in place of your typical cocktail dresses.

  • 9 of 21

    Proenza Schouler Tiger-Print Flocked Jacquard Mini Skirt ($850) in Navy/Jade

    An edgy designer skirt is an investment that you’ll reach for repeatedly.

  • 10 of 21

    Finders Keepers Wildfire Skirt ($120) in Black/White

    You’ll get plenty of use out of this minimal skirt.

  • 11 of 21

    Milly Lace Skirt ($375) in Black/Blush

    Dress down this lacy piece with a casual t-shirt and pointy-toe flats.

  • 12 of 21

    H&M Textured-Weave Skirt ($35) in Zebra Print

    Come fall, you’ll want to wear this neutral animal-print skirt with opaque tights and ankle boots.

  • 13 of 21

    Victoria Beckham Denim Skirt ($380) in Blue

    Depending on your profession, this sleek denim skirt might be refined enough for the office.

  • 14 of 21

    LOFT Autumn Bloom Pencil Skirt ($70) in Golden Mustard

    Pair this skirt with a chambray top through summer, and with a slouchy cardigan for fall.

  • 15 of 21

    Isabel Marant Adelaide Wool-Blend Wrap Mini Skirt ($505)

    Isabel Marant’s skirt proves that wrap-style versions are always cool.

  • 16 of 21

    A.L.C. Bell Print Skirt ($444) in Black/Camel

    You’ll be the best-dressed at the office in A.L.C.’s chic print.

  • 17 of 21

    River Island Blue Check Floral Print Midi Skirt ($70)

    The combination of plaid and bold florals makes this an eye-catching piece.

  • 18 of 21

    Ted Baker Falda Structured Tulip Skirt ($248) in Silver

    The skirt’s tulip shape and its understated color speak to our feminine sensibilities.  

  • 19 of 21

    Nasty Gal Naomi Skirt ($68)

    This cobalt blue skirt’s tasteful front slit adds an interesting element.

  • 20 of 21

    Y'S Faux Wrap Skirt ($690) in Black

    An adjustable drawstring waistband makes this wrap skirt ultra-comfortable.


  • 21 of 21

    Sandro Jaisy Skirt ($275) in Leopard

    Sandro’s leopard print-skirt features a unique sporty waistband.

    What’s your favorite skirt style to wear when transitioning from summer to fall? Tell us in the comments below!

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