Casual Dresses
Casual fall dresses that keep up with your plans—coffee runs, brunch dates, weekend hangs, and everything in between. Slip into long-sleeve silhouettes, cozy sweater knits, and soft ribbed jersey styles that make getting dressed feel easy. Go fitted in a bodycon mini, keep it polished with a midi, or lean into a long, flowy shape for an effortless finish. Layer your favorites with the season’s latest jackets for a look that feels warm, styled, and ready for whatever lands on your calendar.
Now Trending
Casual Dresses Made for Everyday Fall Plans
Windsor’s casual dresses make everyday styling easy with comfortable fabrics, relaxed silhouettes, and trend-right details for workdays, weekends, and everything in between. From breezy cotton and linen-blend day dresses to colored denim, playful prints, and cozy seasonal layers, these one-and-done looks help you feel polished without overthinking the outfit.
Easy Prints, Textures & Layers for the Season
Give your everyday dresses a fall refresh with polka dots, stripes, gingham, ditsy florals, and colored denim that add personality without making styling complicated. When temperatures dip, explore sweater dresses for an easy cozy layer that works with boots, jackets, and cold-weather accessories.
What Makes a Dress Casual?
A casual dress combines comfortable fabrication, an easy-to-wear silhouette, and details that fit naturally into everyday plans. Cotton and linen blends feel breathable and relaxed, while uncomplicated prints and laid-back shapes make getting dressed quick. The best casual dresses also leave room to change the vibe with your shoes, layers, and accessories instead of requiring a completely new outfit.
How Do You Transition a Casual Dress From Summer to Fall?
Start with a lightweight dress you already love, then add pieces that bring warmth without weighing down the look. Style a ditsy floral dress or plaid mini with ankle boots and a cardigan, or layer a colored denim dress with a fitted long sleeve as cooler weather arrives. Switching warm-weather sandals for boots and adding a jacket lets your favorite day dresses stay in rotation longer.
Which Fabrics Work Best for Everyday Dresses?
Think about comfort, movement, and the weather ahead. Cotton and linen blends are breathable choices for warmer transitional days, while knits add softness and extra warmth as fall turns to winter. On colder days, pair knit everyday dresses with tights, tall boots, and a coat for an easy outfit that feels cozy while still looking put together.
How Can You Style One Casual Dress for Different Plans?
Start simple and let your layers and accessories switch up the vibe. Wear a casual midi or skater dress with sneakers and a crossbody bag for daytime plans, then add ankle boots, jewelry, and a Windsor belt when dinner gets added to the group chat. An adjustable belt can define your waist, dress up a laid-back look, or layer with other belts for a more statement-making finish—and it works just as easily over dresses, tops, and jackets. Want more ways to remix your everyday looks? Discover how to blend relaxed pieces with statement details in Windsor’s sporty chic style guide. When winter arrives, add tights, tall boots, a cozy cardigan, or a polished coat for extra warmth. That day-to-evening and season-to-season flexibility is what makes casual dresses a closet favorite for fall and winter.
-
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 knit fabric with knit lining
- Halter plunge neckline with beaded bar strap
- Open back with lace-up design, lower back zipper with hook-eye closure
- Floral applique
- Bodycon mini-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000605
Category Name: Casual Dresses
Price: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
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: $25.97 $56.90
On Sale: Yes
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
-
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: $19.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
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, no-slip strip, padded cups, 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: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
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: $26.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
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: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
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
-
Weekend Away Strapless Maxi Dress
This chevron maxi dress hugs in all the right places with a sleek strapless neckline and leg-baring side slit that was practically made for resort dinners, sunset cocktails, and strolling the beachside town.
Fit & Features
- Chevron pattern, crochet fabric, smooth knit lining
- Strapless neckline
- Side slit
- Form-hugging fit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000595
Category Name: Casual Dresses
Price: $20.97 $46.90
On Sale: Yes
Availability: In Stock
Available Color: MULTI
Available Size: XS, S, M
Product Badge:- Sale
-
Twice As Nice Halter Ruffle Mini Dress
Date night just found its favorite dress. This halter mini dress serves a plunging neckline and a tiered ruffle skirt that moves with you from cocktails to the dancefloor.
Fit & Features
- Knit-lined fabric
- Plunge halter neckline
- Open back
- Form-hugging fit
- Tiered ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05103-000816
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Daydream Detour Paisley Maxi Dress
Easy, floaty, and somehow always the prettiest thing in your closet. This floral paisley maxi dress features a flowy silhouette, lace trim details, and an open tie back that feels made for brunch, weekend markets, and sunny day plans.
Fit & Features
- Floral paisley print, woven fabric, short woven lining
- V-neckline, spaghetti straps
- Open tie-back
- Center front button-up closures
- Flowy maxi silhouette, sheer lace trim
- Runs true to size
Style Number/Barcode: 05102-000592
Category Name: Casual Dresses
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Center Of Attention Floral Maxi Dress
This is the dress that gets the double-take. Designed with a curve-hugging mermaid silhouette and oversized floral print, it brings major romance with a little bit of drama.
Fit & Features
- Statement floral print, lined mesh fabric, high stretch
- Strapless tube neckline
- Curve-hugging, mermaid fit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000593
Category Name: Casual Dresses
Price: $19.97 $42.90
On Sale: Yes
Availability: In Stock
Available Color: BURGUNDY
Available Size: S
Product Badge:- Sale
-
Coast To Cocktails Striped Maxi Dress
The dress that belongs in your vacation photo dump. With a plunging halter neckline, textured striped knit, and an open tie-back design, this maxi dress was made for ocean views, dinner reservations, and weekend escapes.
Fit & Features
- Striped pattern, sheer texture crochet knit fabric
- Halter neckline, tie straps
- Open tie-back
- High side slit
- Curve-hugging, long hem
- Runs true to size
Style Number/Barcode: 05102-000591
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: In Stock
Available Color: NATURAL
Available Size: XS, S, M, L
Product Badge:- Sale
-
Salt Air Striped Knit Cutout Maxi Dress
Vacation photos are optional, but compliments won't be. This striped knit cutout maxi dress hugs your curves with statement O-ring details and a leg-baring slit that was made for turning heads.
Fit & Features
- Abstract striped textured knit fabric, moderate stretch
- Sleeveless sweetheart neckline
- O-ring halter design, tie-back halter spaghetti straps
- Waist cutout with O-ring design
- Open back, bar strap with hook-eye closure, lower back zipper closure
- Maxi-length hem, high-cut side slit, bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000590
Category Name: Casual Dresses
Price: $19.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Café Date Polka Dot Midi Dress
A little flirty, a little polished, and ready for wherever the day takes you. This polka dot midi dress combines a flattering lace-up corset bodice, sweetheart neckline, and leg-baring slit for an effortless look for brunch, showers, or weekend plans.
Fit & Features
- Polka dot pattern, linen-blend woven fabric, woven lining
- Drawstring bust tie square neckline
- Adjustable shoulder straps
- Side zipper and hook-eye closure, lace-up back detail
- Corset bodice, flexible boning, drop waist seam
- Front slit, A-line midi silhouette
- Runs true to size
Style Number/Barcode: 05102-000587
Category Name: Casual Dresses
Price: $54.90
Availability: In Stock
Available Color: NATURAL
Available Size: XS, S, M
-
Spice Done Right Mesh Midi Dress
Too good to save for just one occasion. This mesh midi dress hugs every curve with ruched detailing and a strapless neckline that makes the whole dress feel a little extra in the best way.
Fit & Features
- Mesh-lined fabric
- Strapless sweetheart neckline
- Back zipper closure
- Bodycon silhouette, ruched detail
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-000588
Category Name: Casual Dresses
Price: $19.97 $46.90
On Sale: Yes
Availability: In Stock
Available Color: ORANGE
Available Size: XS, S, M, L, XL
Product Badge:- Sale
-
Extra Flirty Ruffle Mini Dress
This is the mini dress you wear when you want something a little extra. The plunging halter neckline, open back, and ruched drop waist hugs your curves, while the tiered ruffle skirt keeps it flirty for parties, birthdays, and spontaneous nights out.
Fit & Features
- Smooth knit fabric with high stretch
- Sleeveless plunging V-neckline
- Tie-back halter straps, open back
- Ruched drop waist
- Tiered ruffled design
- Mini-length hem, A-line silhouette
- Runs true to size
Style Number/Barcode: 05103-000811
Category Name: Casual Dresses
Price: $39.90
Availability: In Stock
Available Color: NAVY, LIGHT, BLUE, RUST-2
Available Size: XS, S, M, L
-
She's Bold Abstract Floral Midi Tube Dress
Fit & Features
- Sleek knit fabric with knit lining, high stretch
- Abstract floral print
- Strapless straight-across neckline, no-slip strip
- Ruched detailing
- Midi-length hem
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000585
Category Name: Casual Dresses
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
One More Pic Button Denim Dress
Serving attitude with every button. This denim mini dress hugs in all the right places with a lace-up back that makes the exit just as good as the entrance.
Fit & Features
- Denim fabric, vintage-inspired wash, high stretch
- Sleeveless baot neckline
- Front button-up closures
- Tailored seams
- Cutout lace-up strappy back
- A-line mini silhouette
- Runs true to size
Style Number/Barcode: 05102-000586
Category Name: Casual Dresses
Price: $49.90
Availability: In Stock
Available Color: DENIM
Available Size: XS, S, M, L
-
Flirty Fit Lace Ruffle Romper
The one that instantly upgrades whatever’s on your calendar. A lace cutout ruffle romper with a flirty fit that’s made for parties, birthdays, and last-minute invites you’re definitely saying yes to.
Fit & Features
- Sheer lace fabric with knit lining, moderate stretch
- Sleeveless plunging V-neckline, bar strap accent
- Halter tie-back spaghetti straps
- Open back, lower tie-back spaghetti straps
- Drop waist
- Tiered ruffled mini-length overlay, skater silhouette, hidden fitted shorts
- Runs true to size
Style Number/Barcode: 06503-000252
Category Name: Casual Dresses
Price: $46.90
Availability: In Stock
Available Color: OFF, WHITE
Available Size: S, M, L
-
Brunch Booked Floral Mini Dress
Serving vacation mood before you've even packed a bag. This floral tube mini dress features a flattering A-line fit that feels effortless for brunch, parties, and every warm-weather plan that pops up.
Fit & Features
- Floral print, lined knit fabric
- Strapless tube neckline
- A-line mini-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000581
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Darling Detail Strapless Midi Dress
Clean lines, zero effort, maximum compliments. This strapless midi dress hugs in all the right places with a textured knit feel that makes dinner plans, celebrations, and last-minute invites look very handled.
Fit & Features
- Textured knit-lined fabric
- Strapless neckline
- Bodycon silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-000578
Category Name: Casual Dresses
Price: $42.90
Availability: In Stock
Available Color: IVORY
Available Size: XS, S, M, L
-
Getaway Ready Floral Print Maxi Dress
Out of office and not checking. This floral hem print maxi dress features a plunge halter neck, front slit, and a cross strap back that brings the drama from every angle. Perfect for packing with you on vacations, honeymoons, or weekend escapes!
Fit & Features
- Smooth knit stretchy fabric, knit lining
- Halter plunge neckline, hardware insert, adjustable cross back straps
- Open back design
- Cutout bosdice
- Flowy maxi-length silhouette with floral hem print
- Runs true to size
Style Number/Barcode: 05102-000576
Category Name: Casual Dresses
Price: $9.97 $64.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Sweet Charm Flower Strap Crochet Mini Dress
Serving shape with a side of charm. This crochet mini dress hugs your curves while the flower strap detail brings just enough sweetness—wear it when you want compliments without trying.
Fit & Features
- Crochet knit fabric with knit lining, moderate stretch
- Lettuce edge trims
- Sleeveless V-neckline
- Adjustable spaghetti straps, front flower accents
- Mini-length hem
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 06005-000318
Category Name: Casual Dresses
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free