Midi Dresses

Show filters
Sort:
Size
Color
Price
All filters
Sort
Loading...

Product Recommendations

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.

  • Casually Sultry Strapless Bodycon Midi Dress

    Strut looking casually sultry in this strapless midi dress that accentuates your curves and can easily be dressed up or down!

    Fit & Features

    • Brushed knit double-lined stretchy knit fabric
    • Strapless neckline
    • Side ruched seams
    • Bodycon silhouette
    • Midi-length hem, side slit
    • Runs true to size

    Style Number/Barcode: 05102-000186

    Category Name: Midi Dresses

    Price: $34.90

    Availability: In Stock

    Available Color: WINE, RED, BROWN

    Available Size: XS, S, M, L

  • Too Dot To Handle Polka Dot Midi Dress

    Bb girl, you're sizzling in this dress! Add a pair of cute booties and a faux leather jacket to complement this 'fit! 

    Fits & Features

    • Adjustable Spaghetti Straps
    • Surplice V Neckline 
    • Side Zipper WIth Hook & Eye Closure 
    • Midi Length Silhouette With Front Slit 
    • Textured Knit Fabric I Polka Dot Design I Unlined
    • Relax Fit I Minimal Stretch 
    • Zipper Not Featured

    Style Number/Barcode: 05101-0761

    Category Name: Midi Dresses

    Price: $14.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Ruched Mesh Bandage Dress

    Dare to show a little skin in this sultry bandage dress! Style it up with a pair of rhinestone earrings and heels to match!

    Fits & Features

    • Sweetheart Neckline 
    • Back Zipper Wth Hook & Eye Closure
    • Sheer Ruched Long Sleeves 
    • Bandage-Style Bodice
    • Mini Length Silhouette I Built-In Bodysuit
    • Ruched, Sheer Mesh Skirt 
    • Form Hugging Fit I Plenty Of Stretch  

    Style Number/Barcode: 06005-0635

    Category Name: Midi Dresses

    Price: $21.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Modern Romance Off-The-Shoulder Sheer Midi Dress

    The sheer midi dress features an off-the-shoulder neckline, a plunging wired v-neck bust, sheer short sleeves, ruching, and a fitted sheer hem accented with a high-side slit. Complete date night outfit with rhinestone heels.

    Fit & Features

    • Partially lined mesh fabrication
    • Off-the-shoulder neckline
    • Plunging wired v-neck, padded bra cups
    • Sheer short sleeves
    • Ruching
    • High side slit
    • Sheer midi length hem
    • Runs true to size

    Style Number/Barcode: 05101-3906

    Category Name: Midi Dresses

    Price: $22.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Bold In Blooms Deep V Midi Dress

    Girl, you are so fab in florals! You'll love sauntering around in the Bold In Blooms mini dress! 

    Fits & Features

    • Dual Spaghetti Straps | Cross At Back
    • Plunging V Neckline | Padded Bust 
    • Back Zipper With Hook & Eye Closue
    • Midi Length Silhouette | Slit At Center Back
    • Smooth Scuba Fabric | Floral Prints Throughout 
    • Curve Hugging Fit 

    Model is 5'6.5" with a 32" bust, 23.5" waist and 35" hips. She is wearing a size small.

    Style Number/Barcode: 05101-0193

    Category Name: Midi Dresses

    Price: $9.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Lace Darling Midi Dress

    Keep it darling in captivating lace in this elegant midi! Pair this sleek dress with pretty pumps to complete your look! 

    Fit & Features 

    • V-Neckline 
    • Lace Shoulder Straps
    • Sheer Floral Lace Back 
    • Floral Lace Hem | Back Center Slit
    • Lined Crepe Fabric 
    • Form Hugging Fit | Moderate Stretch 

    Style Number/Barcode: 05101-0733

    Category Name: Midi Dresses

    Price: $18.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Floral Vibes Scuba Midi Dress

    Wow everybody in the Floral Vibes midi dress! We envision you wearing this at that outdoor wedding you got invited to or that winery date with your girls 

    Fits & Features

    • Spaghetti Straps Cross At The Back 
    • V Neckline 
    • Midi Length Silhouette 
    • Smooth Scuba Fabric I Floral Prints 
    • Form Hugging Fit I Plenty Of Stretch 
    • Zipper Not Featured

    Style Number/Barcode: 05101-0176

    Category Name: Midi Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Brook High Slit Midi Dress

    Special Occasion 

    Make it a formal affair in our cocktail ready Brook midi dress! Her high slit brings the drama, perfectly pairs with sleek stilettos and rhinestone accents!

    Fit & Features 

    • Off The Shoulder Neckline | Fold Over Accent
    • Slim Fit Bodice
    • Lined Smooth Knit Fabric
    • High Side Slit
    • Midi Length Silhouette 
    • Form Hugging Fit 
    • Moderate Stretch 

     

    Special Occasion products cannot be returned to any retail locations.

    Style Number/Barcode: 05001-0372

    Category Name: Midi Dresses

    Price: $22.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Tamra Cross Neck Midi Formal Dress

    Special Occasion

    Try out a little soft glam in our Tamra formal midi dress! She is sexy, sultry and gives you that soft touch of glam!

    Fit & Features

    • Cross neckline
    • Sleeveless
    • Form fitting silhouette
    • Mid-length hem that hits mid-calf
    • Small slit center front
    • Zipper located center back
    • Moderate stretch

    Special Occasion products cannot be returned to any retail locations.

    Style Number/Barcode: 05001-0325

    Category Name: Midi Dresses

    Price: $29.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Floral Asymmetric Ruched Midi Dress

    Add some flower power to your look with this bold and beautiful midi dress! Goes amazing with some strappy heels 

    Fits & Features

    • Adjustable Spaghetti Straps That Cross At The Back 
    • V Neckline | Lined At The Bust
    • Midi Length Asymmetric Hemline 
    • Side Ruching 
    • Woven Fabric With Floral Prints
    • Plenty Of Stretch | Form Hugging Fit  
    • Zipper Not Featured

     

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

    Style Number/Barcode: 05102-0333

    Category Name: Midi Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Clarice Applique Bodycon Satin Midi Formal Dress

    Special Occasion

    Dressing up is always fun with the Clarice satin midi formal dress! This elegant dress boasts a pretty beaded applique bust, sleek bodycon fit, and a flirty front slit for effortless movement.

    Fit & Features

    • Stretch satin fabric, sewn-in knit lining
    • Beaded applique bust, sweetheart pleated neckline
    • Padded bra cups
    • Adjustable spaghetti straps
    • Back zipper and hook-eye closure
    • Bodycon silhouette, front slit, midi-length hem
    • Runs true to size

     

    Where to Wear:

    Prom, weddings, garden parties, engagement parties, rehearsal dinners, fancy date nights, cocktail soirees

    Style Number/Barcode: 05001-000005

    Category Name: Midi Dresses

    Price: $64.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S

  • Brush It Off Shoulder Crepe Midi Dress

    Brush away those negative vibes, throw on this poppin' midi, and hit the town with your girls! Accessorize with some sparkling gems to really amp up your look.

    Fits & Features

    • Elastic, Off Shoulder Neckline & Short Sleeves
    • Midi Length Silhouette 
    • Crepe Composition 
    • Form Hugging Fit I Plenty Of Stretch 
    • Zipper Not Featured

    Style Number/Barcode: 05101-0664

    Category Name: Midi Dresses

    Price: $9.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Garden Parties Pleated Midi Dress

    Get ready for garden parties, backyard brunches, bridal showers, and spring weddings with this spring staple! Pair with wrap heels, or strappy mules!

    Fit & Features

    • Tie halter neckline
    • Pleated bodice with keyhole cut out
    • Smocked stretchy waist line
    • Pleated flowy skirt 
    • Mid-length hemline
    • Lightweight sheen polyester material
    • Unlined | Moderate stretch

    Model is 5'6" with 31" bust, 26" waist and 36" hips. She is wearing a size small. 

    Style Number/Barcode: 05101-0724

    Category Name: Midi Dresses

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • One Of A Kind One Shoulder Knit Midi Dress

    Look at you strut with that one of a kind style! A knit midi dress with a little sass is all you need! Style with sneaks and a ball cap for a sexy casual look, or dress up with heels!

    Fit & Features

    • Off shoulder slanted neckline
    • One long sleeve
    • Double cut out mid waist with self tie hip
    • Form fitting silhouette
    • Mid length hemline
    • Ribbed knit material with moderate stretch
    Model is 5'8" with a 32" bust,  23" waist and 36" hips. She is wearing a size small.  

    Style Number/Barcode: 06005-0431

    Category Name: Midi Dresses

    Price: $17.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • What's The Ruche Midi Dress

    A look we honestly can't get enough of! Slip into this form-hugging midi dress and show off those never-ending curves!

    Fits & Features

    • Spaghetti Straps
    • Square Neckline
    • Midi Length Silhouette
    • Woven Fabric I Fully Lined
    • Ruching Throughout 
    • Form Hugging Fit I Curve Hugging Fit 

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

    Style Number/Barcode: 05102-0463

    Category Name: Midi Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Button Down Knit Midi Dress

    For the modest yet trendy babe! This midi is a closet staple, whether it's work wear or a casual date night, just throw on some heels and you are lookin' gooood bb!

    Fit & Features

    • V- neckline | Long sleeves
    • Oil slick buttons down the center
    • Mid-length hemline
    • Ribbed knit material
    • Moderate stretch
    • Form fitting silhouette

    Style Number/Barcode: 06005-0516

    Category Name: Midi Dresses

    Price: $20.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Meet Your Match Midi Dress

    You've met your match in this stunning and sultry midi dress! Its color block pattern highlights and flatters your curves.

    Fit & Features

    • Spaghetti straps
    • Wired deep sweetheart neckline
    • Exposed back zipper | Hook and eye closure
    • High waist
    • Mid-length, form hugging fit | Small back slit
    • Color block pattern
    • Ponte knit fabric | Moderate stretch

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

    Style Number/Barcode: 05101-0720

    Category Name: Midi Dresses

    Price: $15.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sprung On Florals Chiffon Midi Dress

    Get sprung over florals this spring! This midi dress is the perfect all occasion piece, whether your going to a shower, a bbq, or brunch, this dress is perf! 

    Fit & Features

    • Scoop drawstring neckline
    • Adjustable spaghetti straps
    • Milkmaid style bodice
    • Fully lined
    • Chiffon | Minimal stretch
    • Ditsy floral print
    • Bust tie detailing | Hidden zipper closure at side
    • Mini length

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

    Style Number/Barcode: 05102-0467

    Category Name: Midi Dresses

    Price: $13.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • A Classic Ribbed Midi Dress

    Look like an instant classic with this curve-hugging sweater dress! The ribbed fabric creates an instant hour-glass illusion! 

    Fit & Features 

    • Off The Shoulder Neckline
    • Long Sleeves
    • Ribbed Knit Fabric 
    • Midi Silhouette
    • Form Hugging Fit
    • Moderate Stretch  

     

    Model is 5'9" with a 32" bust, 23" waist and 34.5" hips. She is wearing a size small.


    Style Number/Barcode: 06005-0417

    Category Name: Midi Dresses

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Simply A Statement Cutout Bodycon Midi Dress

    Simplicity can be a statement! Flaunt your figure in this bodycon midi dress perfect for date nights, brides, and graduation girlies.

    Fit & Features

    • Mesh-lined fabric
    • V-neckline with metal insert, spaghetti straps
    • Underbust cutout
    • Bodycon silhouette
    • Center back slit, midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-4151

    Category Name: Midi Dresses

    Price: $44.90

    Availability: In Stock

    Available Color: IVORY

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

  • Crepe Off Shoulder Fold Over Midi Dress

    You'll be wowing everyone with this timeless dress! Add a pair of accent duster earrings to really elevate your ensemble. 

    Fits & Features

    • Off Shoulder Neckline 
    • Fold Over Design
    • Midi Length Silhouette 
    • Crepe Fabric 
    • Curve Hugging Fit | Ample Stretch
    • Zipper Not Featured

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

    Style Number/Barcode: 05101-0474

    Category Name: Midi Dresses

    Price: $13.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • V In The Midi Dress

    You'll want to slip right into this cozy and sexy midi dress! Pair with some cute heels and a leather jacket for the perf finishing touches. 

    Fits & Features

    • V Neckline & Back 
    • Long Fitted Sleeves 
    • Midi Length Silhouette 
    • Ribbed Knit Fabric 
    • Curve Hugging Fit 

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

    Style Number/Barcode: 06005-0394

    Category Name: Midi Dresses

    Price: $15.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Color Block Knit Mini Dress

    Keep it chic in stand out color block! This mini dress is perf to pair with your fav booties or strappy heels to easily dress up or down! 

    Fit & Features 

    • Mock Neck 
    • Sleeveless 
    • Color Block Design 
    • Ribbed Knit Fabric
    • Mini Length Silhouette 
    • Form Hugging Fit 
    • Moderate Stretch 

     Model is 5'4" with 32" bust, 23" waist and 38" hips. She is wearing a size small.     

    Style Number/Barcode: 06005-0432

    Category Name: Midi Dresses

    Price: $17.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Ruffle Square Neck Smocked Midi Dress

    Show off your figure in this body-lovin' midi dress! Add a cute pair of heels to level up your 'fit. 

    Fits & Features 

    • Short Sleeves I Elastic Shoulders & Cuffs
    • Square Neckline 
    • Tiered Ruffle Trim Along The Bodice & Skirt 
    • Midi Length Silhouette I Ruffle Hem
    • Smocking All Over
    • Woven Fabric 
    • Form Hugging Fit I Plenty Of Stretch 

    Model is 5'8" with a 32" bust, 26" waist and 38" hips. She is wearing a size small. 

    Style Number/Barcode: 05102-0597

    Category Name: Midi Dresses

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance