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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.

  • Valery Faux Leather Corset Midi Dress

    Special Occasion

    Made for the kind of entrance that turns heads without trying, the Valery faux leather corset midi dress brings a sleek, sculpted allure. The structured bodice, curve-skimming silhouette, and thigh-high slit work together to deliver that sultry, eyes-follow-you energy.

    Fit & Features

    • Coated faux leather fabric with a glossy finish
    • Strapless neckline with structured seaming
    • Corset-inspired bodice paneling
    • Back zipper with hook-eye closure
    • Front slit adds movement
    • Midi-length bodycon silhouette
    • Runs true to size

     

    Where to Wear:

    Rooftop party, dressed-up dinner, formal date night, birthday celebration, and nights in the city.

    Style Number/Barcode: 05001-000596

    Category Name: Midi Dresses

    Price: $69.90

    Availability: In Stock

    Available Color: RED

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

  • Glam Obsessed Glitter Off-The-Shoulder Midi Dress

    This is the dress you reach for when you want the room to feel a tiny bit obsessed. The glitter knit hugs just right, the off-the-shoulder neckline adds that soft-but-sultry vibe, and the midi length keeps it effortlessly elevated.

    Fit & Features

    • Glitter knit fabric with moderate stretch
    • Sweetheart neckline with off-the-shoulder sleeves
    • All-over ruched detailing defines the figure
    • Midi-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05101-000543

    Category Name: Midi Dresses

    Price: $49.90

    Availability: In Stock

    Available Color: HUNTER

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

  • Endless Allure Satin Cowl Neck Midi Dress

    This dress feels like that slow-motion walk-in moment everyone secretly wants. The satin glides with every step, the cowl neckline dips just right, and the midi length keeps the whole look effortlessly elevated for anything from date nights to rooftop plans.

    Fit & Features

    • Premium satin fabric with a smooth, luxe drape and no stretch
    • Deep cowl neckline with halter straps
    • Open back with wide self-tie closure
    • Side slit enhances movement
    • Midi-length slim-fit silhouette
    • Runs true to size

    Style Number/Barcode: 05101-000746

    Category Name: Midi Dresses

    Price: $54.90

    Availability: In Stock

    Available Color: WHITE

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

  • Sweep Me Away Ribbed Off Shoulder Midi Dress

    This is that “effortless but still unbelievably chic” dress you reach for when you want comfort without sacrificing the vibe. The ribbed knit hugs smoothly, the foldover neckline drapes just right, and the side slit keeps things subtly daring.

    Fit & Features

    • Soft ribbed knit fabrication, smooth lining
    • Foldover off shoulder neckline
    • Long fitted sleeves
    • Side slit design
    • Midi-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000452

    Category Name: Midi Dresses

    Price: $44.90

    Availability: In Stock

    Available Color: BLACK

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

  • Styled To Stun Mesh Midi Dress

    A dress with quiet-but-deadly allure, this mesh sleeve midi dress blends sleek structure with sheer drama. Its ruched body and sculpted square neckline make it the perfect pick for nights when you want subtle sophistication with a little edge.

    Fit & Features

    • Stretch mesh fabric, knit lining
    • Square neckline with sheer mesh long sleeves
    • Back keyhole with zipper closure
    • Bodycon silhouette
    • Ruched midi skirt with back slit for movement
    • Runs true to size

    Style Number/Barcode: 05101-000781

    Category Name: Midi Dresses

    Price: $49.90

    Availability: In Stock

    Available Color: BLACK

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

  • Starlit Sweetheart Sparkle Midi Dress

    A little glam, a little flirty, this glitter-kissed midi was made for nights that deserve a glow-up moment. The sweetheart neckline and sleek spaghetti straps create an effortlessly sculpted fit perfect for dinner dates, parties, and any excuse to shine.

    Fit & Features

    • Glitter stretch fabric, knit lining
    • Sweetheart neckline with spaghetti straps
    • Smooth fitted bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000416

    Category Name: Midi Dresses

    Price: $42.90

    Availability: In Stock

    Available Color: BLACK

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

  • In Your Element Off-Shoulder Mesh Twist Midi Dress

    This midi knows how to move—soft mesh, abstract swirls, and an off-shoulder twist that feels effortlessly seductive. The high side slit adds that perfect hint of drama, making every step a little more intentional.

    Fit & Features

    • Abstract printed mesh fabric, knit lining
    • Off-shoulder neckline with twist detail
    • Bodycon silhouette
    • High side slit for ease of movement
    • Runs true to size

    Style Number/Barcode: 05102-000372

    Category Name: Midi Dresses

    Price: $39.90

    Availability: In Stock

    Available Color: BROWN

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

  • Floral After Dark Burnout Lace-Up Midi Dress

    This midi brings that velvet-after-dark energy with a floral burnout finish that catches every bit of light. The lace-up open back and soft cowl neckline balance sultry details with a sleek, sculpted silhouette that feels effortlessly elevated.

    Fit & Features

    • Velvet burnout fabric
    • Spaghetti straps with a soft cowl neckline
    • Open lace-up back for adjustable shaping
    • Body-skimming mermaid silhouette
    • Midi length with subtle flare at the hem
    • Runs true to size

    Style Number/Barcode: 05101-000749

    Category Name: Midi Dresses

    Price: $52.90

    Availability: In Stock

    Available Color: BLACK

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

  • Effortless Impact Mock Neck Midi Dress

    This midi is your secret weapon—clean, sculpting, and quietly commanding. The ribbed knit dress smooths and contours while the mock neck adds that cool, editorial structure that never tries too hard.

    Fit & Features

    • Rib knit fabric
    • Mock neckline
    • Smooth bodycon fit
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000479

    Category Name: Midi Dresses

    Price: $39.90

    Availability: In Stock

    Available Color: HUNTER

    Available Size: XS, S, M, L

  • Polished Curves Off-Shoulder Knit Midi Dress

    This midi dress keeps it classy with a side of allure—the foldover neckline, sleek rib knit, and gold hardware detail turn a timeless silhouette into a subtle showstopper. It’s the kind of dress that makes minimal feel magnetic.

    Fit & Features

    • Rib knit fabric
    • Foldover off-shoulder neckline with hardware accent
    • Long fitted sleeves
    • Bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000232

    Category Name: Midi Dresses

    Price: $44.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

    Product Badge:
    • Best Seller
  • Soft Radiance Satin Cowl Midi Dress

    This dress is pure quiet luxury—soft satin drape, a fluid cowl neckline, and a silhouette that glides without trying too hard. It’s the kind of dress that turns a simple event into a golden-hour moment at dressy parties, date nights, and celebrations!

    Fit & Features

    • Woven satin fabric with subtle sheen
    • Adjustable spaghetti straps
    • Cowl neckline with soft drape
    • Fitted bodice with contoured seaming
    • Midi-length mermaid silhouette
    • Exposed back zipper closure
    • Runs true to size

    Style Number/Barcode: 05101-000814

    Category Name: Midi Dresses

    Price: $54.90

    Availability: In Stock

    Available Color: GOLD

    Available Size: XS, S, M, L

  • Luminous Form Bodycon Midi Dress

    This midi dress brings soft glamour into focus with a draped cowl neckline, pleated bust, and a curve-skimming fit that feels both polished and flirty. The ruching at the waist adds that extra bit of shape, giving you a silhouette that’s clean but far from simple.

    Fit & Features

    • Soft knit satin-like fabric with subtle sheen
    • Cowl neckline with pleated bust detail
    • Adjustable spaghetti straps
    • Ruched bodice creating a contoured waist
    • Midi-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05101-000351

    Category Name: Midi Dresses

    Price: $39.90

    Availability: In Stock

    Available Color: BLACK

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

  • Murphy Faux Leather Midi Formal Dress

    Special Occasion 

    Crafted to command attention, this faux leather midi dress sculpts a striking silhouette with its sweetheart neckline and sleek bodycon fit. Designed with a refined side slit that adds movement and allure, it delivers a polished yet bold statement for your most elevated evenings. 

    Fit & Features

    • Faux leather fabric with smooth coated finish
    • Sweetheart bustier neckline with structured seaming
    • Built-in padded underwire bust
    • Adjustable spaghetti straps
    • Pleated waist detail, side zipper and hook-eye closure
    • Midi-length pencil silhouette with side slit
    • Runs true to size

    Where to Wear:

    Art gallery openings, cocktail lounges, date nights, bachelorettes, fashion-forward dinner parties, birthday celebrations, VIP concert suites, elevate night out event

    Style Number/Barcode: 05001-000595

    Category Name: Midi Dresses

    Price: $69.90

    Availability: In Stock

    Available Color: BROWN

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

  • Evening Smooth Strapless Sash Midi Dress

    This strapless midi dress is the definition of clean glamour—smooth curves, subtle ruching, and a cascading side sash that adds the perfect amount of drama. It’s refined, confident, and ready to elevate any evening lineup.

    Fit & Features

    • Sleek woven fabrication with subtle sheen
    • Strapless tube neckline with smooth, structured bodice
    • Ruched side waist with cascading sash detail
    • Bodycon midi-length silhouette
    • Runs true to size

    Style Number/Barcode: 05101-001061

    Category Name: Midi Dresses

    Price: $42.90

    Availability: In Stock

    Available Color: NAVY, BROWN

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

    Product Badge:
    • New Arrival
  • Rosewater Romance Chiffon Midi Dress

    This is the dress you wear when you want soft-girl magic with a little plot twist. The floral chiffon floats with every step, the cowl neckline gives that effortless drape, and the lace-up back seals the deal with subtle drama. Finished with a high slit and cascading ruffles, she’s basically a walking love letter.

    Fit & Features

    • Floral-printed jacquard chiffon fabric with subtle textured finish
    • Cowl neckline with spaghetti straps
    • Side cascading ruffle with high front slit
    • Open back with lace-up back closure, hidden zipper and hook-eye closure
    • Midi-length silhouette
    • Runs true to size

    Style Number/Barcode: 05101-000803

    Category Name: Midi Dresses

    Price: $56.90

    Availability: In Stock

    Available Color: NATURAL

    Available Size: XS, S, M, L

    Product Badge:
    • New Arrival
  • Laylin Velvet Lace-Up Midi Formal Dress

    Special Occasion

    Designed for evenings that call for confidence and quiet drama, the Laylin velvet bodycon midi dress moves with intention and allure. A square neckline, wrap front slit, and lace-up open back create a silhouette that feels sculpted, modern, and unmistakably polished.

    Fit & Features

    • Velvet-lined fabric with soft stretch
    • Square neckline with wide tank straps
    • Ruched wrap-style skirt with front slit
    • Midi-length silhouette
    • Lace-up back detail
    • Runs true to size

     

    Where to Wear:

    Weddings, formal holiday parties, rehearsal dinners, evening cocktail receptions, romantic dates, engagement parties, birthdays, cultural events, fancy occasions

    Style Number/Barcode: 05001-000597

    Category Name: Midi Dresses

    Price: $59.90

    Availability: In Stock

    Available Color: WINE

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

    Product Badge:
    • Best Seller
  • Delicate Drama Ruched Midi Dress

    This dress is all about subtle drama done right. With sheer sleeves, a draped neckline, and ruching that moves with you, it gives that effortlessly pulled-together feel from every angle.

    Fit & Features

    • Sheer mesh fabric with high stretch
    • Cowl neckline with halter-style spaghetti straps
    • Long sheer sleeves
    • Ruched detailing throughout the body
    • Midi-length silhouette
    • Runs true to size

    Style Number/Barcode: 05101-000782

    Category Name: Midi Dresses

    Price: $36.90

    Availability: In Stock

    Available Color: BLACK

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

    Product Badge:
    • Best Seller
  • Satin Glow Strapless Beaded Midi Dress

    This dress is the definition of quiet luxury with a wink—sleek satin, a beaded corset-style bodice, and a strapless neckline that lets your shoulders do their thing. The draped skirt adds that soft, sculpted movement, perfect for celebrations where you want to look effortlessly elevated.

    Fit & Features

    • Strapless straight neckline with structured beaded mesh bodice
    • Intricate floral beading and sequin embellishments on bodice
    • Draped satin skirt with soft cowl detail at the waist
    • Midi-length satin silhouette with gentle flare at the hem
    • Back zipper and hook-eye closure
    • Runs true to size

    Style Number/Barcode: 05101-000744

    Category Name: Midi Dresses

    Price: $54.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: S, M, L, XL

    Product Badge:
    • Best Seller
  • Meghan Faux Leather Corset A-Line Formal Dress

    Special Occasion

    The Meghan dress delivers modern polish with a confident edge, designed to feel striking yet effortlessly refined. Smooth faux leather meets a sculpted corset bodice and sweetheart neckline, flowing into an a-line midi silhouette that moves beautifully and feels undeniably elevated.

    Fit & Features 

    • Faux leather structured fabric, stretch knit lining
    • Sweetheart neckline with adjustable spaghetti straps
    • Corset-structured bodice, flexible boning for shaping
    • Back zipper and hook-eye closure
    • Convenient hidden side pockets
    • Pleated A-line midi-length silhouette
    • Runs true to size

     

    Where to Wear:

    Social events, cocktail parties, art openings, fashion-forward events, birthday dinners, date nights, bridal showers, cultural events, corporate events

    Style Number/Barcode: 05001-000613

    Category Name: Midi Dresses

    Price: $139.90

    Availability: In Stock

    Available Color: BROWN

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

    Product Badge:
    • Ships Free
  • Date Night Defined Long Sleeve Midi Dress

    This ruched midi dress is all about sculpted elegance with a confident edge. Designed with sheer mesh long sleeves and a sweetheart neckline, it highlights the waist with soft ruching that flatters from every angle. The subtle front cutout adds intrigue, while the open-back detail and back slit keep the look refined yet undeniably alluring.

    Fit & Features

    • Smooth knit fabric
    • Sweetheart neckline with center front cutout
    • Long fitted mesh sleeves
    • Ruched bodice and skirt construction
    • Back zipper closure
    • Back slit at hem
    • Runs true to size

    Style Number/Barcode: 05101-000805

    Category Name: Midi Dresses

    Price: $49.90

    Availability: In Stock

    Available Color: WINE

    Available Size: XS, S, M, L

  • Plans After Sunset Midi Dress

    This is the kind of dress that doesn’t need an intro. Sleek, sculpted, and subtly shimmering, it moves with intention and lands every eye in the room.

    Fit & Features

    • Rhinestone floral detailing, mesh-lined fabric
    • V-neckline with halter spaghetti straps
    • Fitted bodice with seam shaping
    • Midi-length skirt with bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05101-000626

    Category Name: Midi Dresses

    Price: $49.90

    Availability: In Stock

    Available Color: RED

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

    Product Badge:
    • New Arrival
  • Quietly Bold Lattice Side Midi Dress

    This is the kind of dress that holds eye contact a second longer. Clean lines up front with a subtle lattice moment down the side make it feel polished, confident, and a little unexpected.

    Fit & Features

    • Ribbed knit fabric with stretch
    • Square neckline
    • Fitted long sleeves
    • Side lattice cutout detailing
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000233

    Category Name: Midi Dresses

    Price: $44.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

    Product Badge:
    • New Arrival
  • Soft Focus Moment Ribbed Knit Midi Dress

    Soft curves, no effort. This ribbed knit midi dress hugs just right with a bodycon fit that moves from dinner plans to late-night photos without missing a beat.

    Fit & Features

    • Sweetheart neckline with twisted bust detail
    • Spaghetti straps
    • Fitted bodice through the waist
    • Bodycon silhouette through the hips
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000397

    Category Name: Midi Dresses

    Price: $39.90

    Availability: In Stock

    Available Color: PINK

    Available Size: XS, S, M, L

    Product Badge:
    • New Arrival
  • Soft Intentions Off-Shoulder Midi Dress

    Soft, sculpted, and quietly confident. This faux cashmere midi dress drapes off the shoulders with a foldover neckline and body-hugging fit that accentuates your curves.

    Fit & Features

    • Faux cashmere knit with a smooth, knit lining
    • Foldover off-the-shoulder neckline
    • Fitted long sleeves
    • Bodycon midi silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000526

    Category Name: Midi Dresses

    Price: $38.90

    Availability: In Stock

    Available Color: WINE

    Available Size: XS, S, M, L

    Product Badge:
    • New Arrival