Casual 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!

  • Simple Charm Gingham Mini Dress

    Feels like a picnic invite just showed up. This gingham mini dress keeps it cute and easy with a collar, cap sleeves, and a button-down front that works from coffee shop hangs to casual plans.

    Fit & Features

    • Gingham pattern, cotton-blend woven fabric, woven lining
    • Collar neckline
    • Cap sleeves
    • Front button-down closures
    • Tie-back strap
    • A-line mini silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000598

    Category Name: Casual Dresses

    Price: $38.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M, L

  • Effortless Confidence Sheer Lace Maxi Dress

    A little sheer, a little bold—exactly how you like it. This lace maxi dress skims your body with a soft stretch feel, made for slipping into when the vibe calls for effortless confidence.

    Fit & Features

    • Textured lace fabric with a mini-length knit lining, moderate stretch
    • Sleeveless V-neckline with O-ring accent at the bust
    • Adjustable spaghetti straps
    • Maxi-length hem
    • Form-hugging silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000599

    Category Name: Casual Dresses

    Price: $44.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M, L

  • Flirting With Drama Lace Ruffle Skater Dress

    A little lace, a lot of attitude. This sheer lace skater dress hugs at the top and flares into flirty, ruffled layers that make every step feel like a moment.

    Fit & Features

    • Sheer lace fabric with partial knit lining, moderate stretch
    • Strapless bodice with smooth woven fabric with sheer lace inserts and trim
    • Sweetheart neckline, front hook-eye closures
    • Open lace-up back design with tie closure
    • Drop waist seam, tiered ruffled design
    • Mini-length skater silhouette
    • Runs true to size

    Style Number/Barcode: 05103-000824

    Category Name: Casual Dresses

    Price: $39.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

  • Coconut Coast Cutout Maxi Dress

    Booked the trip and packed this tropical maxi dress that brings vacay vibes with a smocked fit, breezy skirt, and just the right amount of skin-baring detail. Pair with sandals and sunnies.

    Fit & Features

    • Tropical palm print, gauze-woven fabric
    • Strapless sweetheart neckline
    • Ruched drawstring tie-front bodice
    • Cutout accent
    • Flowy maxi silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000601

    Category Name: Casual Dresses

    Price: $59.90

    Availability: In Stock

    Available Color: NATURAL

    Available Size: XS, S, M, L

    Product Badge:
    • New Arrival
  • Cool Confidence Animal Print A-Line Mini Dress

    A little wild, a lot unforgettable. This strappy abstract animal print A-line mini dress skims and sways with every step, giving you that effortless, throw-it-on-and-own-the-night kind of confidence.

    Fit & Features

    • Mesh fabric with knit lining, high stretch
    • Abstract animal print
    • Sleeveless sweetheart neckline, no-slip strip
    • Cross-front spaghetti strap design leading to a tie-back halter design
    • Open back design
    • Mini-length asymmetric hem, flowy A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05103-000823

    Category Name: Casual Dresses

    Price: $39.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Small Town Stunner Denim Mini Dress

    Giving county fair flirt with a side of sassy. This strapless denim mini dress mixes corset-inspired seam detailing with a tiered poplin hem that makes every head turn. Pair with sandals for any sunny day plans or events.

    Fit & Features

    • Denim fabric, slight stretch
    • Strapless sweetheart neckline, poplin ruffle trim, non-slip grip lining
    • Padded bra cups, back zipper and hook-eye closure
    • Corset-inspired seam detailing
    • Bodycon fit
    • Poplin side ruffle panels, mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000603

    Category Name: Casual Dresses

    Price: $69.90

    Availability: In Stock

    Available Color: DENIM

    Available Size: XS, S, M, L

  • Brown Sugar Breeze Cutout Maxi Dress

    This strapless maxi dress brings the kind of effortless allure that looks good from beach strolls to walks back to the hotel. The smocked fit, soft cutout detail, and flowy skirt keep it stylish with a pair of sandals.

    Fit & Features

    • Gauze woven fabric
    • Strapless sweetheart neckline
    • Stretchy smocked bodice with cutout
    • Flowy maxi-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000602

    Category Name: Casual Dresses

    Price: $56.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M, L

  • Golden Hour Crochet Halter Dress

    Booked for golden hour and not coming back early. This crochet halter mini dress features floral appliqué and a lace-up back that keeps things effortlessly pretty with just enough detail to stand out.

    Fit & Features

    • Crochet texture-lined knit fabric
    • Halter plunge neckline with beaded strap
    • Open back with lace-up design
    • Floral applique 
    • Bodycon mini-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000605

    Category Name: Casual Dresses

    Price: $52.90

    Availability: In Stock

    Available Color: NATURAL

    Available Size: XS, S

  • Island Nights Mesh Halter Maxi Dress

    Vacay booked. This tropical mesh maxi dress brings that breezy, curve-skimming fit with a trendy ruffled slit that moves with you from beach cocktails to dinner.

    Fit & Features

    • Tropical print, mesh fabric, soft knit lining
    • Halter V-neckline with hardware insert
    • Tie straps, open back
    • High front ruffled slit
    • Curve-hugging maxi silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000607

    Category Name: Casual Dresses

    Price: $49.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Vacation Flirt Knit Cutout Maxi Dress

    Serving vacation flirt and trendy vibes. This knit maxi dress hugs in all the right places with lace-up cutouts, a plunging halter neckline, and an open back that knows exactly what it’s doing.

    Fit & Features

    • Knit fabric with flame stitch pattern
    • Sleeveless plunging V-neckline, beaded strap
    • Tie-back halter straps
    • Lace-up side cutouts
    • Open back, lower tie-back spaghetti straps
    • Back zipper and hook-eye closure
    • Maxi-length bodycon silhouette, back slit accent
    • Runs true to size

    Style Number/Barcode: 05102-000606

    Category Name: Casual Dresses

    Price: $48.90

    Availability: In Stock

    Available Color: MULTI

    Available Size: XS, S, M, L

  • Raise A Toast Mesh Bodycon Midi Dress

    Made for wedding invites, cocktail receptions, and the kind of nights that deserve extra photos. This strapless mesh midi dress sculpts your figure with flattering ruching and a draped side sash that brings the drama.

    Fit & Features

    • Mesh-lined fabric
    • Strapless neckline
    • Wrap side sash detail
    • Back zipper closure, center back slit accent
    • Ruched bodycon midi-length silhouette
    • Runs true to size

    Style Number/Barcode: 05101-001186

    Category Name: Casual Dresses

    Price: $46.90

    Availability: In Stock

    Available Color: LIGHT, BLUE-2

    Available Size: XS, S, M, L

  • Weekend Flare Paisley Skater Mini Dress

    Your weekend lineup just got cuter. This paisley mesh skater dress features delicate straps and a flowy tiered hanky hem that moves with every step, making it an easy pick for any sunny day plans.

    Fit & Features

    • Paisley print, mesh-lined fabric
    • V-neckline
    • Adjustable spaghetti straps
    • Flowy skater silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000610

    Category Name: Casual Dresses

    Price: $19.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Garden Party Glow Floral Halter Midi Dress

    Soft, sweet, and lowkey stealing all the attention. This floral halter midi dress hugs just right with a flattering fit that’s perfect for brunch plans, date nights, or any last-minute invite.

    Fit & Features

    • Lightweight eyelet fabrication with soft lining
    • Sleeveless halter neckline
    • Delicate floral pattern
    • Fitted bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000609

    Category Name: Casual Dresses

    Price: $36.90

    Availability: In Stock

    Available Color: WHITE

    Available Size: XS, S, M, L

  • Sunset Stunner Mesh Strapless Midi Dress

    Hot plans, zero overthinking—this dress just gets it. A sleek strapless mesh midi that hugs in all the right places and shows up ready for every RSVP on your calendar.

    Fit & Features

    • Lightweight mesh fabric with stretch lining
    • Bodycon midi silhouette
    • Strapless straight neckline
    • Abstract print with contouring effect
    • Runs true to size

    Style Number/Barcode: 05102-000611

    Category Name: Casual Dresses

    Price: $42.90

    Availability: In Stock

    Available Color: ORANGE

    Available Size: XS, S, M, L

  • Soft Spoken Statement Linen V Neck Maxi Dress

    Quiet luxury, but make it cool girl. This linen V-neck maxi dress skims the body with an easy drape, delicate straps, and lace panel details that feel effortless for dinner plans, gallery nights, or that last-minute RSVP.

    Fit & Features

    • Lightweight linen blend fabrication
    • Sleeveless v-neckline
    • Adjustable spaghetti straps
    • Lace panel inserts
    • Maxi-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000614

    Category Name: Casual Dresses

    Price: $28.97 $64.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BLACK

    Available Size: S, M

    Product Badge:
    • Sale
  • Bad Decisions Denim Mini Dress

    This dress definitely starts stories. The denim bodycon mini dress features lace-up side details and corset seam shaping that hugs close and pairs perfectly with boots, tiny bags, and plans that were never fully confirmed.

    Fit & Features

    • Denim fabric, slight stretch
    • Strapless tube neckline, non-slip grip lining
    • Back zipper and hook-eye closure
    • Side lace-up plackets with bungee cords
    • Corset-seamed bodice
    • Bodycon mini-length silhouette
    • Runs true to size

    Style Number/Barcode: 05103-001126

    Category Name: Casual Dresses

    Price: $59.90

    Availability: In Stock

    Available Color: DENIM-2

    Available Size: XS, S, M, L

  • Spritz And Plans Strapless Mini Dress

    This dress has "take me on vacay" written all over it! The playful print and easy strapless fit keep it light, while the flowy mini hem makes it perfect for enjoying a sunny day on your next getaway.

    Fit & Features

    • Garden fruit and veggie print, woven fabric, stretchy knit lining
    • Strapless neckline, stretchy smocked bodice
    • Fit and flare silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000617

    Category Name: Casual Dresses

    Price: $19.97 $32.90

    On Sale: Yes

    Availability: In Stock

    Available Color: IVORY

    Available Size: XS, S, M, L

    Product Badge:
    • Sale
  • Miss Me Yet Abstract Babydoll Mini Dress

    Serving just enough cuteness with every step. This abstract print chiffon babydoll dress features a plunge V-neckline with studded trim and an open back that practically guarantees compliments before you even make it to dinner.

    Fit & Features

    • Abstract print, chiffon fabric, smooth woven lining
    • Plunge V-neckline with a studded trim bust
    • Open back, adjustable spaghetti straps
    • Babydoll mini-length silhouette, hanky hem
    • Runs true to size

    Style Number/Barcode: 05103-000851

    Category Name: Casual Dresses

    Price: $49.90

    Availability: In Stock

    Available Color: GRAY

    Available Size: XS, S, M, L

  • Vacay State Of Mind Tropical Print Maxi Dress

    Vacation state of mind, no passport required. This tropical print maxi dress hugs you in all the right places with a sleek bodycon fit and bold cutout details that feel both effortless and elevated.

    Fit & Features

    • Knit fabric with high stretch, soft knit lining
    • Tropical print
    • Strapless neckline
    • Triple bust cutouts and oval-shaped hardware accents
    • Maxi-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000622

    Category Name: Casual Dresses

    Price: $46.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M, L

  • Second Glance Beaded-Trim Halter Midi Dress

    The kind of dress that gets a second glance before you even say a word. This beaded-trim halter midi dress hugs in all the right places with a textured knit feel, open lace-up sides, and an open back that makes every entrance look intentional.

    Fit & Features

    • Textured knit fabric, high stretch, knit lining
    • Sleeveless V-neckline, beaded bar strap accent
    • Tie-back halter spaghetti straps, beaded accents
    • Open back, lower tie-back spaghetti straps, back zipper closure
    • Open lace-up side design
    • Midi-length hem, back slit detail, bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000627

    Category Name: Casual Dresses

    Price: $49.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M, L

  • Island Heat Mesh Maxi Dress

    Booked, busy, and dressed like it. This tropical floral maxi dress is form-hugging with a high side slit that brings just enough drama for your next getaway or sunset dinner.

    Fit & Features

    • Tropical floral print, mesh fabric, brushed knit lining
    • Strapless tube neckline, non-slip grip lining
    • High side slit
    • Form-hugging fit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000626

    Category Name: Casual Dresses

    Price: $45.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Paradise Found Halter Mini Dress

    Straight into the vacation outfit folder. This textured knit mini dress features playful side cutouts and cascading bead details that bring just the right amount of drama to beach cabanas, tropical dinners, and every photo-worthy plan.

    Fit & Features

    • Texture knit fabric, smooth kint lining
    • High halter neckline, tie straps
    • Open tie-back, lower zipper and hook-eye closure
    • Side cutouts with beaded fringe trim
    • Bodycon fit
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000628

    Category Name: Casual Dresses

    Price: $52.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: XS, S, M, L

  • Ruffle Rush Tropical Floral Mini Dress

    Booked trip or just booking attention, this tropical floral ruffle mini dress gets the invite. The stretchy lined mesh, halter cowl neckline, open back, and flowy ruffled sash bring flirty movement with a fitted A-line shape.

    Fit & Features

    • Mesh fabric with knit lining, high stretch
    • Tropical floral print
    • Sleeveless cowl neckline
    • Tie-back halter straps, open back, lower tie-back spaghetti straps
    • Asymmetric tiered ruffled design, ruffled side sash accent
    • Mini-length hem, fitted A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000624

    Category Name: Casual Dresses

    Price: $49.90

    Availability: In Stock

    Available Color: MULTI

    Available Size: XS, S, M, L

    Product Badge:
    • New Arrival
  • Blush Blossom Halter Mini Dress

    A little flirty mini dress, a little romantic, and made for sunny plans. This embroidered floral halter mini dress features a soft A-line shape that skims the body, while the delicate tie front and open back keep the look playful.

    Fit & Features

    • Embroidered floral woven fabric
    • Halter neckline with adjustable tie
    • Front tie detail at bust
    • A-line silhouette with mini-length hem
    • Hidden back zipper closure
    • Runs true to size

    Style Number/Barcode: 05102-000630

    Category Name: Casual Dresses

    Price: $44.90

    Availability: In Stock

    Available Color: SAGE, PINK

    Available Size: M, L