Casual Dresses

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Cute Sweater Dresses

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Everyday Ease: Casual Dresses for Transitional-Weather Plans

From weekend brunches to spontaneous coffee runs, Windsor’s casual dresses deliver easygoing style with just the right amount of polish. These effortlessly chic looks move with you—whether you’re off to the farmers’ market or catching golden hour with friends. Layer your favorite long sleeve to keep the chill out, or pick your Windsor shoes and accessories, and you're ready for the day.

Laid-Back & Versatile

Knit, ribbed, crochet, and sweater dresses bring comfort and style to cooler days. Slip into playful mini dresses, flowy midi styles, or long casual dresses in warm neutrals, jewel tones, and classic plaids. T-shirt and tunic dresses with trendy necklines, ruching, or cutouts make “throw on and go” feel totally styled.

Chic from Day to Night

Swap sneakers for ankle boots to take your favorite midi dress from errands to evening hangs. A flowy maxi in nuetral or black adds relaxed elegance—just add a faux leather jacket and heeled booties for an effortless finish.

Ready to refresh your everyday looks? Explore Windsor’s full collection of casual dresses online, in-app, or in-store.

What Makes a Dress Casual?

Casual dresses are defined by their effortless styling, comfortable fabrics, and laid-back details. Fabrication plays a key role—soft knits, cotton blends, and breezy silhouettes naturally create an easygoing look. Prints like ditsy florals or neutral-tone patterns, such as snake print, also make great everyday choices. Knit and sweater dresses are perfect for relaxed settings, whether you're heading to work or dressing up for a casual date night.

Styling is just as important in making a dress feel casual. Swap heels for sneakers, lug boots, or strappy sandals to instantly dress down your look. Layering is another effortless way to create a relaxed aesthetic—throw on a denim jacket, cropped sweater, or oversized cardigan for a cool, laid-back vibe. Details like drawstrings, button fronts, and tie accents also add to the casual appeal. Accessories, makeup, and hair styling can further influence the look, so opt for dainty jewelry, natural waves, or a simple ponytail to complete your effortlessly stylish outfit.

How Do I Style a Dress Casually?

Styling a dress casually is all about choosing relaxed layers and accessories that balance comfort with fashion. Denim jackets, graphic tees, scrunchies, crossbody bags, and sneakers all contribute to an effortlessly cool aesthetic. Try pairing a ruched mini dress with a lariat necklace and chunky sneakers for a sporty yet chic look. A basic knit midi dress layered under a cropped denim jacket with slides is perfect for a casual-chic feel.

For road trips or weekend getaways, maxi and midi dresses offer an easy styling solution. Layer a lightweight sweater over a flowy maxi or knot a t-shirt at the waist for a trendy, carefree vibe. Combat boots can add an edgy touch, while simple strappy sandals keep the outfit light and airy. No matter your style, Windsor has a versatile collection of casual dresses and must-have accessories to complete your look. Need styling help? Visit us in-store, and our expert stylists will help you find your perfect outfit!

  • Cute Entrance Polka Dot Ruffle Skater Dress

    Polka dots, ruffles, and a strapless moment? Say less. This flirty skater dress features a stretchy smocked bodice and tiered ruffled silhouette that’s made for brunch dates, party pics, and any plan that calls for a cute entrance.

    Fit & Features

    • Woven fabric
    • Polka dot print
    • Strapless straight-across neckline, ruffled trim
    • Stretchy smocked bodice
    • Tiered ruffled design
    • Short skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000532

    Category Name: Casual Dresses

    Price: $44.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

    Product Badge:
    • Back In Stock
  • RSVP Ready Sash Mini Dress

    When the invite says dress up, this dress understood the assignment. This eyelet tube bodycon mini dress hugs in all the right places and finishes with a draped side sash that brings the drama to showers, parties, or day dates.

    Fit & Features

    • Eyelet fabric, knit lining
    • Tube strapless necklinenon-slip grip lining
    • Attached side ruffle sash
    • Bodycon mini-length fit
    • Runs true to size

    Style Number/Barcode: 05102-000530

    Category Name: Casual Dresses

    Price: $19.97 $34.90

    On Sale: Yes

    Availability: In Stock

    Available Color: PINK, WHITE

    Available Size: XS, L

    Product Badge:
    • Sale
  • Ocean Daydream Seashell Mini Dress

    Catch flights or just compliments in this mini dres that hugs just right with delicate shell details and a breezy open back made for sunny getaways and golden hour dinners.

    Fit & Features

    • Crochet knit-lined fabric with seashell embellishments
    • V-neckline
    • Spaghetti straps shape the lace-up back design
    • Bodycon fit
    • Ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000536

    Category Name: Casual Dresses

    Price: $52.90

    Availability: In Stock

    Available Color: NATURAL

    Available Size: XS, S, M, L

    Product Badge:
    • Best Seller
  • Chic Moments Bodycon Mini Dress

    Clean lines. Bold presence. This chic bodycon mini dress hugs just right with a sleek mock neckline that keeps the vibe elevated, whether you’re heading out late or dressing up a last-minute plan.

    Fit & Features

    • Sleeveless mock neckline
    • Mini-length hem
    • Bodycon silhouette
    • Smooth knit fabric with high stretch
    • Runs true to size
    • Please note the necklace is not included

    Style Number/Barcode: 05102-000539

    Category Name: Casual Dresses

    Price: $30.90

    Availability: In Stock

    Available Color: BLACK, BURGUNDY, BROWN, NAVY

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

    Product Badge:
    • Best Seller
  • Rosé Forecast Floral Poppy Mini Dress

    Felt cute, will definitely post. With its floral poplin print and flirty skater silhouette, this mini dress was made for brunches, showers, and being the best dressed at the winery.

    Fit & Features

    • Floral poppy print, cotton-blend woven fabric, woven lining
    • Square neckline, adjustable spaghetti straps
    • Back zipper and hook-eye closure
    • Skater silhouette
    • Bonded mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-001090

    Category Name: Casual Dresses

    Price: $56.90

    Availability: In Stock

    Available Color: NATURAL

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

  • Last Minute Plans Denim Skater Dress

    This dress was made for day or night casual plans when you wanna look cute. The structured corset-inspired bodice flatters in all the right places while the flirty skater skirt keeps it playful.

    Fit & Features

    • Dark wash denim fabric with stretch
    • Sweetheart neckline
    • Adjustable spaghetti straps
    • Back zipper and hook-eye closure
    • Corset-seamed bodice
    • Skater mini-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000538

    Category Name: Casual Dresses

    Price: $49.90

    Availability: In Stock

    Available Color: DARK, DENIM

    Available Size: XS, S, M, L

  • No Questions Asked Mini Dress

    This one doesn’t wait around. Command the room in this bodycon mini dress, offering a show of skin and a trendy hardware detail that pulls the look together. Pair with heels for a night out.

    Fit & Features

    • Texture knit fabric
    • Plunge cutout neckline, hardware insert
    • Adjustable spaghetti straps
    • Cutout back
    • Bodycon mini-length silhouette
    • Runs true to size

    Style Number/Barcode: 06005-000309

    Category Name: Casual Dresses

    Price: $36.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: S, M, L

  • Flirting With Plans Puff Sleeve Skater Dress

    She’s cute, collected, and already has plans you’ll want in on. This puff sleeve skater dress cinches in all the right places with a breezy fit that works for dinner reservations, summer parties, and every “I had nothing to wear” moment.

    Fit & Features

    • Linen-blend woven fabric
    • Sweetheart neckline, bust tie detail
    • Short puff sleeves
    • Open tie-back design
    • Short skater silhouette, ruffled hem
    • Runs true to size

    Style Number/Barcode: 05102-000542

    Category Name: Casual Dresses

    Price: $49.90

    Availability: In Stock

    Available Color: NAVY

    Available Size: XXS, XS, S, L

    Product Badge:
    • Best Seller
  • Dinner Plans Locked Mock Neck Wrap Midi Dress

    Clean lines, subtle drama, zero hesitation. This ribbed midi dress hugs in all the right places with a sleek wrap detail that does the talking from reservations to late plans.

    Fit & Features

    • Ribbed knit fabric with stretch
    • Mock neckline with long sleeves
    • Wrap-style skirt with hardware detail
    • Front slit at hem
    • Midi-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000544

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Brunch Flirt Polka Dot Ruffle Skater Dress

    Sweet and flirty, this polka dot mesh babydoll dress brings the ruffle, the lace-up back, and that floaty skater shape that’s made for brunch plans and your fab weekend festivities.

    Fit & Features

    • Mesh fabric with lining
    • Dainty polka dot print
    • Sleeveless V-neckline, ruched bust and bodice
    • Adjustable spaghetti straps
    • Open cross-back lace-up design, tie closure
    • Tiered ruffled short skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-001099

    Category Name: Casual Dresses

    Price: $20.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Hot Plans Tropical Tube Mini Dress

    Booked, busy, and dressed for it. This tropical floral mini dress hugs in all the right places with a sleek strapless fit—made for vacations, beach weekends, and last-minute plans that turn into everything.

    Fit & Features

    • Tropical floral print, stretchy knit fabric
    • Tube strapless neckline
    • Bodycon mini-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000547

    Category Name: Casual Dresses

    Price: $35.90

    Availability: In Stock

    Available Color: BLUE

    Available Size: XS, S, M, L

  • Soft Spoken Confidence Rib Knit Mini Dress

    Low effort, high payoff. This rib knit foldover off-the-shoulder mini dress hugs just enough while keeping things comfortable, perfect for dinners that turn into late plans.

    Fit & Features

    • Soft rib knit fabric with stretch and lining
    • Foldover off-the-shoulder neckline
    • Long sleeve design
    • A-line mini silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000545

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BURGUNDY

    Available Size: L

  • Ultra Game NBA NY Knicks Mini Dress

    Serving courtside energy even when you’re not at the game. This NBA Knicks halter mini dress hugs in all the right places with a sporty lace-up detail that keeps it playful and bold.

    Fit & Features

    • Jersey knit fabric, smooth knit lining
    • Halter contrast trim neckline with tie straps
    • Lace-up neckline with front and back Knicks graphic team logo
    • Corset bodice, flexible boning
    • Side zipper and hook-eye closure
    • Bodycon mini-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000548

    Category Name: Casual Dresses

    Price: $49.90

    Availability: In Stock

    Available Color: WHITE

    Available Size: XS, S, M, L

    Product Badge:
    • Best Seller
  • Ultra Game NBA LA Lakers Mini Dress

    Game night, but make it stylish. This Los Angeles Lakers tube mini dress snatches with a structured bodice while the embroidered team logo and stud accents keep it bold from every angle.

    Fit & Features

    • Sleek knit-lined stretchy fabric
    • Strapless tube neckline, padded bra cups
    • Los Angeles Lakers embroidered team logo, mini stud accents
    • Lace-up back design, side zipper and hook-eye closure
    • High waist seam
    • Bodycon mini-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000549

    Category Name: Casual Dresses

    Price: $23.97 $52.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

    Product Badge:
    • Sale
  • Stylish Plans Ribbed Knit Bodycon Midi Dress

    One of those dresses that somehow does all the styling for you. This ribbed knit bodycon midi dress hugs just right with a notched V-neckline and sleek silhouette that works from casual plans to dressed-up moments.

    Fit & Features

    • Ribbed knit fabric, high stretch
    • Sleeveless scoop neckline, notched V-neckline
    • Thin tank shoulder straps
    • Back slit accent
    • Midi-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000552

    Category Name: Casual Dresses

    Price: $42.90

    Availability: In Stock

    Available Color: BLUE

    Available Size: S, L

  • Favorite Thing Sleeveless Midi Dress

    The kind of dress that somehow works for every plan on your calendar. This rib knit bodycon midi dress keeps it chic and simple, perfect for dressing up or down.

    Fit & Features

    • Rib knit fabric, double-lined, stretchy
    • Sleeveless scoop neckline
    • Tank shoulder straps
    • Bodycon silhouette
    • Side slit, midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000551

    Category Name: Casual Dresses

    Price: $39.90

    Availability: In Stock

    Available Color: BROWN, IVORY

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

  • Barely Trying Open Back Midi Dress

    This is that effortless dress you reach for when you want to feel cute and put together. The open back adds a soft, unexpected moment, while the ribbed fit keeps everything sleek and flattering.

    Fit & Features

    • Rib knit stretchy fabric
    • Scoop neckline
    • Spaghetti straps
    • Open back
    • Side slit
    • Form-hugging, midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000553

    Category Name: Casual Dresses

    Price: $39.90

    Availability: In Stock

    Available Color: YELLOW

    Available Size: M, L

  • Desert Heat Faux Suede Strapless Mini Dress

    This mini dress is doing the most in the best way. The faux suede strapless dress hugs in all the right places while the curved fringe detail brings the drama for nights out or festival plans.

    Fit & Features

    • Faux suede fabric, smooth knit lining
    • Strapless neckline, non-slip grip lining
    • Back zipper and hook-eye closure
    • Bodycon fit
    • Curved seam detailing, curved front fringe trim
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000555

    Category Name: Casual Dresses

    Price: $19.97 $42.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S

    Product Badge:
    • Sale
  • Flirt First Strapless Lace Tiered Mini Dress

    Sweet at first glance, bold once you turn around. This strapless lace mini dress hugs through the bodice and finishes with playful tiered ruffles—made for nights that start casual and end unforgettable.

    Fit & Features

    • Stretch lace-lined fabric with a soft, floral texture
    • Strapless neckline
    • Drop waist silhouette
    • Tiered ruffle skirt
    • Mini length hem
    • Runs true to size

    Style Number/Barcode: 05102-000557

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet Plans Ahead Long Sleeve Skater Dress

    Soft, cute, and already booked. This ribbed skater dress hugs up top and floats just right at the hem, making it an easy yes for brunches, daytime plans, and V-day dates!

    Fit & Features

    • Pointelle knit soft stretch fabric
    • Crew neckline
    • Fitted long sleeves
    • Fitted bodice with a defining drop waist seam
    • Ruffled skater silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000556

    Category Name: Casual Dresses

    Price: $19.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Flirting In Positano A-Line Mini Dress

    Meet the dress equivalent of booking the flight before asking questions. With its dreamy coastal print and easy strapless fit, this mini dress was made for European getaways, brunch, and sunny day plans.

    Fit & Features

    • Multi-print design, linen-blend woven fabric, woven lining
    • Strapless neckline, non-slip grip lining
    • Side hidden zipper and hook-eye closure
    • Bar back accent and cutout
    • A-line fit
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000561

    Category Name: Casual Dresses

    Price: $44.90

    Availability: In Stock

    Available Color: MULTI

    Available Size: XS, S, M, L

  • Such A Vibe Ribbed Knit Mini Tube Dress

    Simple, chic, and such a vibe. This ribbed knit mini tube dress hugs your curves with a comfy stretch fit—made for plans that come together at the last minute, but you still look fab.

    Fit & Features

    • Hacci ribbed knit fabric, high stretch, knit lining
    • Strapless fold-over neckline
    • Mini-length hem
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000562

    Category Name: Casual Dresses

    Price: $35.90

    Availability: In Stock

    Available Color: LIGHT, BLUE

    Available Size: XS, S, M, L

  • Flirty Chic Cutout Maxi Dress

    The kind of dress that makes every plan feel a little more chic. With its flowy silhouette, flirty cutout detail, and side pockets, this maxi dress was made for vacations, weekend plans, and showers.

    Fit & Features

    • Gauze cotton woven fabric, woven lining
    • Sweetheart neckline, spaghetti straps
    • Open tie-back design
    • Cutout bodice
    • Hidden side pockets
    • Flowy maxi-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000559

    Category Name: Casual Dresses

    Price: $46.90

    Availability: In Stock

    Available Color: WHITE

    Available Size: XS, S, M, L

  • Wine Night Pinstripe Mini Dress

    Clock out, but keep the attitude. This pinstripe mini dress brings tailored energy up top and flirty drama at the hem, hugging you in all the right places for wine bar nights and dinner.

    Fit & Features

    • Pinstriped pattern, woven fabric, sewn-in knit lining
    • Strapless lace trim sweetheart neckline
    • Padded bra cups
    • Back zipper and hook-eye closure
    • Ruched side lace panels
    • Form-hugging fit, ruffled mini hem
    • Runs true to size

    Style Number/Barcode: 05102-000558

    Category Name: Casual Dresses

    Price: $46.90

    Availability: In Stock

    Available Color: WINE

    Available Size: XS, S, M, L