Midi Dresses

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Fall & Winter Midi Dresses You’ll Live In

Welcome your cold‑weather glow with midi dresses that bring warmth and wow. Our curated edit of mid-length dresses blends cozy knit, velvet, satin, and stretch crepe to keep you wrapped in chic style all season long. Dress them up or down—this is the collection that proves midi dresses aren’t just for sunshine.

Winter Nights, Office Days, Holiday Evenings

From formal midi dresses for gala nights to midi holiday party dresses that shine under string lights, we’ve got every vibe covered. Think long sleeves, mock necks, and rich jewel tones for upscale events. When you want a touch of edge, reach for a midi club dresses silhouette with cutouts or ruching that plays up bodycon lines while still delivering mid-length elegance.

Styles That Work Overtime

In our fall/winter midi line, expect figure-flattering details like ruching, wrap waists, off-shoulder necklines, and asymmetric hems. Cozy yet sleek ribbed knits, ponte, and sweater fabrics make daytime wear effortless—pair with a moto jacket or trench. For evening, slip into velvet or satin mid-length dresses that catch candlelight and camera flashes alike. With pockets, adjustable straps, and stretch back panels, each piece solves styling hiccups so you look composed from date to dance floor.

Layering is everything this season—add a cropped faux fur, a tailored blazer, or sheer long-sleeve mesh underneath. Pair with knee-high boots or strappy heels depending on the look. Whether you're heading to the office, a holiday soirée, or dinner with friends, our midi dresses adapt to your schedule and mood.

Fall & Winter Midi Dresses You’ll Live In

Welcome your cold‑weather glow with midi dresses that bring warmth and wow. Our curated edit of mid-length dresses blends cozy knit, velvet, satin, and stretch crepe to keep you wrapped in chic style all season long. Dress them up or down—this is the collection that proves midi dresses aren’t just for sunshine.

Winter Nights, Office Days, Holiday Evenings

From formal midi dresses for gala nights to midi holiday party dresses that shine under string lights, we’ve got every vibe covered. Think long sleeves, mock necks, and rich jewel tones for upscale events. When you want a touch of edge, reach for a midi club dresses silhouette with cutouts or ruching that plays up bodycon lines while still delivering mid-length elegance.

Styles That Work Overtime

In our fall/winter midi line, expect figure-flattering details like ruching, wrap waists, off-shoulder necklines, and asymmetric hems. Cozy yet sleek ribbed knits, ponte, and sweater fabrics make daytime wear effortless—pair with a moto jacket or trench. For evening, slip into velvet or satin mid-length dresses that catch candlelight and camera flashes alike. With pockets, adjustable straps, and stretch back panels, each piece solves styling hiccups so you look composed from date to dance floor.

Midi Dresses in Every Shade—With Holiday Styling Tips

Explore our curated midi collections in every hue, with outfit ideas that transition effortlessly from festive dinners to gift swaps and winter weddings:

  • Black Midi Dresses: Pair a sleek black midi with pointed-toe pumps and a structured blazer for an office party look that turns into dinner-ready elegance.
  • Blue Midi Dresses: Go bold with cobalt blue styled under a faux fur jacket and metallic heels for a festive night out with friends.
  • Green Midi Dresses: Elevate your holiday presence in an emerald green midi paired with gold statement earrings and velvet ankle boots.
  • Pink Midi Dresses: A blush pink midi with soft satin finish and nude heels is perfect for a winter bridal shower or holiday brunch.
  • Red Midi Dresses: Command attention in a scarlet red midi, styled with a faux leather moto jacket and black booties for party-season drama.
  • White Midi Dresses: For winter formals or seasonal celebrations, opt for a white midi layered with a crystal-embellished belt and silver heels.

Shop Windsor’s midi dresses online, in-store, or in-app—and fall in love all over again. From cozy daytime looks to ultra-glam formal midi dresses and midi holiday party dresses, your new go-to mid-length dresses await.

  • Sweetheart Bustier Ruched Midi Dress

    You are sizzlin' in this sexy number! It's the perf night out dress for a GNO!

    Fits & Features

    • Adjustable Spaghetti Straps
    • Sweetheart Neckline I Bustier Style, Padded Bust
    • Back Zip With Hook & Eye Closure
    • Midi Length Silhouette I Slit At Side
    • Mesh Lined Fabric 
    • Curve Hugging Fit I Ample Stretch
    • Ruching All Over 

    Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.

      Style Number/Barcode: 05101-0737

      Category Name: Midi Dresses

      Price: $9.97 $44.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Cowl Neck Front Slit Midi Dress

      This swoon-worthy dress was made for you! 

      Fits & Features

      • Spaghetti Straps With Dual Straps At Back 
      • Cowl Neckline I Square Back 
      • Midi Length Silhouette I Front Slit 
      • Zipper Not Featured
      • Smooth Jersey Knit Fabric I Fully Lined 
      • Curve Hugging Fit I Moderate Stretch 

      Model is 5'9" with a 34" bust, 24" waist and 35.5" hips. She is wearing a size small. 

        Style Number/Barcode: 05101-0413

        Category Name: Midi Dresses

        Price: $12.97 $33.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Ships Free
      • An Instant Classic Midi Dress

        This midi will have you looking like an instant classic with its commanding high slit and button deets! Pair this beauty with sleek stilettos and a luxe clutch for a look that is ready for a night out! 

        Fit & Features 

        • Strapless Square Neckline 
        • Button Accents with Lion Engraved Design 
        • High Side Slit 
        • Lined Ribbed Knit Fabric
        • Midi Length Silhouette 
        • Form Hugging Fit 
        • Moderate Stretch 


         

        Style Number/Barcode: 06005-0544

        Category Name: Midi Dresses

        Price: $15.97 $38.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Clearance
      • Addison Formal Wrap Midi Dress

        Special Occasion 

        Stunningly timeless, Addison brings an elegant aura to your special moments! She features an off the shoulder neckline, a wrapped sweetheart bust, off the shoulder cap sleeves with ruched detailing and a midi length silhouette with an asymmetrical hem. Dress is composed of a lined crepe fabric that offers a curve hugging fit with a moderate stretch.

        Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small

         

        Special Occasion products cannot be returned to any retail locations.

        Style Number/Barcode: 05001-0230

        Category Name: Midi Dresses

        Price: $19.97 $44.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Sale
      • Button Down Tie Front Midi Dress

        A casual midi dress with chic details! Slip into some mules and you're all set for those daytime festivities with your girls! 

        Fits & Features

        • Bust Tie & Faux Button Front Design 
        • Short Sleeves I Elastic Cuffs & Shoulders 
        • Midi Length Silhouette 
        • Rib Knit Fabric 
        • Form Hugging Fit I Moderate Stretch 
        • Zipper Not Included

        Style Number/Barcode: 05102-0720

        Category Name: Midi Dresses

        Price: $9.97 $44.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Clearance
      • Sleek Style High Slit Bodycon Midi Dress

        This sleek and smooth knit midi dress features a ruched V-neckline with thin tank shoulder straps, flattering princess seams down the length of the dress, and a high-cut front slit for added movement. The bodycon silhouette will showcase your gorgeous curves. Perfect for cocktail hour, style with stilettos.

        Fit & Features

        • Smooth knit fabric with plenty of stretch
        • Ruched V-neckline
        • Tank shoulder straps
        • Princess seams
        • High front slit
        • Midi-length bodycon fit
        • Runs true to size

        Style Number/Barcode: 05101-3703

        Category Name: Midi Dresses

        Price: $34.90

        Availability: In Stock

        Available Color: HUNTER

        Available Size: XS, S, M, L, XL

      • Kenzie Formal Lattice Midi Dress
        Special Occasion 


        Lace-up in luxe satin as you make a captivating entrance in our Kenzie dress! She features a sleeveless bodice, a plunging V-neckline with padded cups, princess seams, and narrow straps that lead to a lattice back detail. Her slim-fit bodice leads to a midi-length silhouette accented with a side slit. The dress is composed of a stretchy satin fabric that offers a form-hugging fit with a moderate stretch. Includes a lower back zipper closure. Complete look with heels and a clutch.

        Fit & Features

        • Sleeveless V-neckline, padded cups
        • Spaghetti straps, lattice back, lower back zipper and hook and eye closure
        • Midi-length silhouette
        • High side slit
        • Lined stretchy satin fabric
        • Form-hugging fit, moderate stretch 
        • Runs true to size

        Style Number/Barcode: 05001-0619

        Category Name: Midi Dresses

        Price: $19.97 $49.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Sale
      • Petal Perfection Cowl Neck Midi Dress

        Charm them all in this pretty midi dress! Soft watercolored petals and a trendy cowl neckline make a romantic combination for this wedding guest dress! 

        Fits & Features

        • Spaghetti Straps That Cross At The Back 
        • Cowl Neckline 
        • Midi Length Silhouette
        • Stretchy Floral Knit Fabric 
        • Form Hugging Fit I Moderate Stretch 
        • Zipper Not Featured 

        Style Number/Barcode: 05101-0662

        Category Name: Midi Dresses

        Price: $9.97 $34.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Clearance
      • Allure Them All Scoop Neck Tank Midi Dress

        Allure them in this knockout sweater midi dress! Perfect for stepping out for a casual lunch date or layer this dress for the perfect workwear outfit. The dress features a scoop neckline, tank-like straps, and a midi-length silhouette. Elevate your look with square toe strappy mules.

        Shop More Sweater Dresses: Sweater Dress Collection

        Fit & Features

        • Tank shoulder straps
        • Scoop neckline and back
        • Midi-length hem
        • Ribbed sweater-knit fabric
        • Plenty of stretch
        • Form-hugging fit
        • Runs true to size

        Style Number/Barcode: 06005-0604

        Category Name: Midi Dresses

        Price: $6.97 $34.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Clearance
      • Flaunt Those Florals Waist Tie Dress

        Work that springtime magic in this pretty and sweet maxi dress! Add a woven bag and wedges for a completed look! 

        Fits & Features

        • Plunging V Neckline 
        • Waist Tie Design 
        • Sleeveless Bodice
        • Maxi Length Silhouette 
        • Woven Fabric I Ditsy Floral Print Design 
        • Relax Fit I Minimal Stretch 

        Style Number/Barcode: 05102-0739

        Category Name: Midi Dresses

        Price: $19.97 $49.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Ships Free
      • You're The One Bodycon Midi Dress

        There's truly no one like you bb girl! With a statement single strap and a figure-hugging fit, you'll be feeling fierce in this basic ribbed dress! 

        Fits & Features

        • One Shoulder Strap 
        • Slanted Neckline
        • Midi Length Hem 
        • Ribbed Knit Fabric 
        • Figure Hugging I Moderate Stretch

        Style Number/Barcode: 05102-0685

        Category Name: Midi Dresses

        Price: $13.97 $34.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Sale
      • Oh My Ruched Asymmetric Dress

        Oh my gawwwwd girl! Flaunt it in this form-hugging dress! We'd love to see you layer this look with rhinestone earrings and heels!

        Fits & Features

        • High Neckline 
        • Spaghetti Straps
        • Drawstring Ruching At The Side 
        • Asymmetric Midi Length Hemline 
        • Stretchy Jersey Knit Fabric I Partial, Mini Length Lining 
        • Form Hugging Fit I Moderate Stretch 

        Style Number/Barcode: 05101-0516

        Category Name: Midi Dresses

        Price: $14.97 $35.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Clearance
      • Pop Of Color Block Ditsy Floral Midi Dress

        Give them a pop of color this season in this flowy dress! Add a pair of block heels and cute mini purse for an OOTD! 

        Fits & Features

        • Tank Shoulder Straps
        • Plunging V Neckline & Back 
        • Back Zipper With Hook & Eye Closure
        • Midi Length I Overlapping Ruffle Trim Hem 
        • Woven Fabric With Ditsy Floral Print & Color Block Design I Partial, Mini Length Lining
        • Relax Fit I Minimal Stretch 

        Style Number/Barcode: 05101-0809

        Category Name: Midi Dresses

        Price: $16.97 $42.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Ships Free
      • Dreamy Petals Off Shoulder Midi Dress

        A picture-perf dress for that girls brunch! Wave your hair out and add some gold-tone jewelry for a spring-ready look! 

        Fits & Features

        • Off Shoulder Neckline & Sleeves
        • Midi Length Silhouette 
        • Smooth Scuba Knit Fabric I Watercolored Florals
        • Form Hugging Fit 
        • Moderate Stretch 

        Style Number/Barcode: 05101-0661

        Category Name: Midi Dresses

        Price: $9.97 $32.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Clearance
      • Cut It Out Babe Midi Dress

        Effortless, but make it extra. With a bold cutout bodice and sleek side slit, this midi dress hugs in all the right places for dates, brunch, or casual plans.

        Fit & Features

        • Stretchy rib knit fabric, contrast trim
        • Square neck, tank shoulder straps
        • Cutout bodice
        • Side slit
        • Bodycon silhouette
        • Midi-length hem
        • Runs true to size

        Style Number/Barcode: 06005-000045

        Category Name: Midi Dresses

        Price: $18.97 $44.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Ships Free
      • Sweet & Smocked Ditsy Ruffle Midi Dress

        Get into the spring vibe with this midi dress on! Easily style it up or down by switching out your white sneakers to heels! 

        Fits & Features

        • Adjustable Spaghetti Straps
        • Square Neckline 
        • Tiered Ruffle Detail 
        • Midi Length Silhouette 
        • Ditsy Woven Print 
        • Form Hugging Fit I Plenty Of Stretch 

        Style Number/Barcode: 05101-0501

        Category Name: Midi Dresses

        Price: $18.97 $46.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Clearance
      • Vanessa Formal Crepe Midi Dress

        Special Occasion

        Keep it classically chic in our elegant Vanessa midi dress! Her off the shoulder neckline is perfect for pairing with a statement necklace and midi length showcases glowing gams! 

        Fit & Features 

        • Off The Shoulder Neckline 
        • Wrap Sweetheart Bust 
        • Princess Seams 
        • Midi Length Silhouette | Wrap Style
        • Lined Crepe Fabric 
        • Form Hugging Fit 
        • Moderate Stretch 


        Special Occasion products cannot be returned to any retail locations.

        Style Number/Barcode: 05001-0397

        Category Name: Midi Dresses

        Price: $19.97 $39.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Ships Free
      • Tortoise O-Ring Ribbed Knit Midi Dress

        Casual and cute, you'll be loving the O-ring belt around this chic midi dress! We love to see you rockin' this with some white sneakers and a faux leather jacket! 

        Fits & Features

        • Spaghetti Straps
        • Scoop Neckline I Square Back
        • Tortoise O-Ring Waist Belt  
        • Midi Length Silhouette 
        • Ribbed Knit Fabric I Fully Lined 
        • Form Hugging Fit I Plenty Of Stretch 
        • Zipper Not Featured

        Style Number/Barcode: 05102-0673

        Category Name: Midi Dresses

        Price: $13.97 $34.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Ships Free
      • You Go Girl Midi Dress

        You go babe! This strapless midi dress will leave 'em speechless! Pair with some espadrille wedges for the perf spring time vibe.

        Fit & Features

        • Strapless sweetheart neckline
        • Padded bust
        • Back zipper
        • High waist seam
        • Mid-length form hugging fit
        • Asymmetric hem | Front slit
        • Textured knit fabric | Moderate stretch | Knit lining

        Style Number/Barcode: 05101-0758

        Category Name: Midi Dresses

        Price: $14.97 $36.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Ships Free
      • Petra Crepe Off Shoulder Midi Dress

        Special Occasion

        With a fold-over, off-shoulder neckline and fitted long sleeves, our Petra exudes class and elegance. Her midi-length hem features a back center slit for you to glide around with ease. Accessorize her with a gorge envelope clutch and a fab pair of heels! 

        Fits & Features

        • Off Shoulder Fold-Over Neckline 
        • Back Zipper Closure
        • Fitted Long Sleeves
        • Midi Length Hemline | Fitted Skirt 
        • Center Back Slit 
        • Crepe Fabric | Fully Lined
        • Form Hugging Fit | Plenty Of Stretch 

         

        Special Occasion products cannot be returned to any retail locations.

        Style Number/Barcode: 05001-0398

        Category Name: Midi Dresses

        Price: $31.97 $59.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Ships Free
      • Get A Move On Crepe Midi Dress

        You need to get a move on with making those GNO plans with your girlfriends! Make sure you pick up this party-ready dress and elevate your style with some bold earrings!

        Fits & Features

        • Spaghetti Straps 
        • Scoop Neckline 
        • Midi Length Silhouette I Front Slit 
        • Crepe Fabric 
        • Form Hugging Fit I Plenty Of Stretch 
        • Zipper Not Featured

        Style Number/Barcode: 05103-0851

        Category Name: Midi Dresses

        Price: $13.97 $35.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Ships Free
      • Turn On The Charm Square Neck Midi Dress

        Slip into this midi dress and watch that confidence skyrocket! Pair this dress with some fab heels and layer on the dainty deets. 

        Fits & Features

        • Bungee Spaghetti Straps
        • Square Neckline 
        • Midi Length Hemline
        • Smooth, Double-Layered Jersey Knit Fabric 
        • Form Hugging Fit I Moderate Stretch

        Style Number/Barcode: 05102-0561

        Category Name: Midi Dresses

        Price: $13.97 $32.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Ships Free
      • Sleeveless Ruched Midi Dress

        Yessssss girl! She's classy and curvy. Up your midi game with this form-hugging dress! Pair it with your fav block heels.

        Fits & Features

        • Crew Neckline
        • Dual Button Closure At Nape I Keyhole Opening
        • Midi Length Silhouette
        • Ruching Throughout 
        • Smooth Jersey Knit Fabric I Fully LIned
        • Form Hugging Fit I Moderate Stretch 
        • Zipper Not Featured

        Style Number/Barcode: 05102-0699

        Category Name: Midi Dresses

        Price: $13.97 $35.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Ships Free
      • Clarabelle Sweetheart A-Line Midi Formal Dress

        Special Occasion

        Romantic and structured, the Clarabelle midi formal dress sculpts and flatters your figure with a sweetheart-fitted bodice and a drop waist seam that perfectly accentuates your waistline along the A-line silhouette.

        Fit & Features

        • Floral and fruit garden print
        • Organza fabric, multiple woven and tulle linings
        • Sweetheart neckline, padded bra cups
        • Adjustable spaghetti straps, back zipper and hook-eye closure
        • Fitted bodice, drop waist seam
        • A-line silhouette, midi-length hem
        • Runs true to size

         

        Where to Wear:

        Prom, weddings, garden parties, fancy parties, milestone celebrations, spring galas

        Style Number/Barcode: 05001-2725

        Category Name: Midi Dresses

        Price: $99.90

        Availability: Out of Stock

        Product Badge:
        • Ships Free