Midi Skirts

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Product Recommendations

Everyday Chic: Midi Skirts for Summer Styling

From café dates to city strolls, Windsor’s midi skirts deliver effortless elegance with trend-forward flair. Breezy silhouettes, high waists, and flowy hems define this collection—designed to flatter and keep you cool through every summer plan.

Lightweight fabrics in floral prints, sleek solids, and classic neutrals offer versatile pairings for casual days or elevated evenings. For daytime looks, pair a cotton or chiffon midi skirt with a cropped tank and slide sandals. Heading out? Opt for a side-slit satin midi styled with strappy heels and statement earrings for rooftop cocktails or weekend dinners.

Whether you’re embracing coastal vibes or brunching in the city, these skirts move with you—blending comfort and sophistication in every step. Explore Windsor’s full collection of midi skirts online, in-app, or at your local Windsor store and elevate your everyday wardrobe.

  • Blissful View Crochet Knit Midi Skirt

    Enjoy stylish bliss in this crochet midi skirt on your next getaway or weekend outing! The skirt offers a flattering high-rise waist, a bodycon fit, and a midi-length hem. Complete the look with the matching halter top.

    Shop Matching Top: Blissful View Halter Crochet Crop Top

    Fit & Features

    • Crochet knit fabric, geometric pattern, knit lining
    • High-rise waist, ribbed detail
    • Midi-length hem
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 06501-1140

    Category Name: Midi Skirts

    Price: $39.90

    Availability: In Stock

    Available Color: LIGHT, BLUE, NATURAL

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set
  • Sensational Match Bodycon Midi Skirt

    Make a sensational impression in this bodycon midi skirt on vacay or brunch! Pair with the matching top to complete the cute look.

    Shop Matching Top: Sensational Match Tie-Front Ruffle Crop Top

    Fit & Features

    • Smooth stretchy double-lined knit fabric
    • High-rise waist
    • Side ruched seams
    • Center back slit
    • Bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 06501-000021

    Category Name: Midi Skirts

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Flirty Ways Ruched High Slit Midi Skirt

    With this flirty midi skirt for celebrations or date night, you'll stun with the ruched detailing and high-cut side slit. Pair with the matching crop top to complete the look.

    Shop Matching Top: Flirty Ways Halter Lace Trim Crop Top

    Fit & Features

    • Stretchy smooth knit fabric with lining
    • High-rise waist
    • Ruching
    • Asymmetric high-side slit
    • Midi-length hem
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06501-000023

    Category Name: Midi Skirts

    Price: $26.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: S, M, L

    Product Badge:
    • Part of a Set
  • Always Happy Hour High-Rise Slit Midi Skirt

    Embrace the sultry vibes of this high-rise slit midi skirt for your next happy hour spree! Pair with the matching top to complete the vibe.

    Shop Matching Top: Always Happy Hour Cowl Neck Crop Top

    Fit & Features

    • Double-lined slinky knit stretchy fabric
    • High-rise waist
    • Side slit
    • Bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 06501-000024

    Category Name: Midi Skirts

    Price: $26.90

    Availability: In Stock

    Available Color: GREEN, RUST

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set
  • Way She Moves Striped Midi Skirt

    This striped midi skirt has entered the girl's vacay chat! Boasting a sexy bodycon silhouette and mid-rise waist, you'll be the hit of the trip. Pair with the matching top to complete the look!

    Shop Matching Top: Way She Moves Striped Bra Top

    Fit & Features

    • Striped print, scalloped trim, stretchy knit fabric
    • Mid-rise waist
    • Bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 06401-0743

    Category Name: Midi Skirts

    Price: $46.90

    Availability: In Stock

    Available Color: BLACK/WHITE

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set
  • In My Feels High-Rise Midi Skirt

    Whether you're on vacay or sitting poolside, this high-rise midi skirt will have you feeling yourself! Pair with the matching top.

    Fit & Features

    • Stretchy knit fabric
    • High-rise waist
    • Column silhouette
    • Midi-length hem
    • Runs true to size

     

    Shop The Matching Top: In My Feels Scoop Neck Bra Top

    Style Number/Barcode: 06501-1138

    Category Name: Midi Skirts

    Price: $34.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set
  • Tropical Energy High-Rise Midi Skirt

    Bring the energy to your destination getaway in this tropical midi skirt, designed with a sleek high-rise waist and form-hugging silhouette. Pair it with the matching top.

    Fit & Features

    • Tropical print, mesh fabric, soft knit stretchy lining
    • High-rise waist
    • Form-hugging silhouette
    • Midi-length hem
    • Runs true to size

     

    Shop The Matching Top: Tropical Energy Strapless Crop Top

    Style Number/Barcode: 06501-000010

    Category Name: Midi Skirts

    Price: $29.90

    Availability: In Stock

    Available Color: TAN

    Available Size: S, M, L

    Product Badge:
    • Part of a Set
  • Serenade Me Bodycon Midi Skirt

    A dreamy look awaits in this sleek bodycon midi skirt with a flattering high-rise waist and center back slit for effortless movement. Pair with the matching top to complete the look!

    Fit & Features

    • Double-lined smooth knit stretchy fabric
    • High-rise waist
    • Bodycon silhouette
    • Center back slit
    • Midi-length hem
    • Runs true to size

     

    Shop The Matching Top: Serenade Me V-Neck Crop Top

    Style Number/Barcode: 06501-000008

    Category Name: Midi Skirts

    Price: $26.90

    Availability: In Stock

    Available Color: BLACK, MOCHA

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set
  • Ruffle Me Up Midi Skirt

    Flirty, flowy, and made for vacay vibes! This ruffle-trim midi skirt brings soft drama with a sleek fit and side slit that shows just enough—pair it with the matching top to complete the look.

    Shop The Matching Top: Ruffle Me Up Crop Top

    Fit & Features

    • Smooth double-lined stretchy knit fabric
    • High-rise waist
    • Side ruched seam and ruffled slit
    • Bodycon fit
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 06501-000060

    Category Name: Midi Skirts

    Price: $28.90

    Availability: In Stock

    Available Color: PINK

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set
  • Summer Crush Striped Crochet Midi Skirt

    POV: you just found your new fave beach-to-brunch vibe. This striped crochet midi skirt serves laid-back heat with a form-hugging fit and thigh-high slit made for turning heads from sunrise to sunset.

    Shop Matching Top: Summer Crush Striped Crochet Bralette Top

    Fit & Features

    • Crochet knit fabric
    • Striped pattern
    • High-rise waist
    • Thigh-high side slit
    • Midi-length hem
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06501-000027

    Category Name: Midi Skirts

    Price: $44.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set
  • Catch The Curve High Slit Midi Skirt

    She’s giving effortless hot. This high slit curve-hugging midi skirt brings sleek movement and a snatched fit that’s all about the slow turn and stare. Perfect for rooftop nights or a content-worthy dinner 'fit.

    Shop Matching Top: Always Happy Hour Cowl Neck Crop Top

    Fit & Features

    • Double-lined slinky knit fabric, high stretch
    • High-rise elasticized waist
    • Ruching
    • High side slit
    • Midi-length hem
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06501-000063

    Category Name: Midi Skirts

    Price: $26.90

    Availability: In Stock

    Available Color: GREEN, BROWN

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set
  • Go With The Vibe Slit Midi Skirt

    Embrace your daring side and let this midi skirt elevate your look. Its sleek high-rise waist and side slit highlight your confidence and flair, perfect for making a statement at any event. Pair with the matching top.

    Shop The Matching Top: Go With The Vibe Halter Crop Top

    Fit & Features

    • Slinky knit stretchy fabric
    • High-rise waist
    • Side pleated hip seam
    • High side slit
    • Form-hugging silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 06501-000062

    Category Name: Midi Skirts

    Price: $29.90

    Availability: In Stock

    Available Color: BURGUNDY

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set