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.
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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.
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Forever Fave Strapless Bodycon Mini Dress
This curve-flaunting mini dress will be a forever fave for rooftop bars or dressy date nights. The textured knit fabric adds a chic allure to the strapless bodycon silhouette.
Fit & Features
- Textured knit fabric, full-length knit lining, high stretch
- Strapless sweetheart neckline, no-slip strip
- Padded bust, bust seam outline
- Back zipper with hook-eye closure
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000190
Category Name: Casual Dresses
Price: $19.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Steal The Scene Floral Corset Ruffle Mini Dress
This floral corset mini dress serves up ruffles, romance, and just the right amount of sass. With its curve-hugging bodice and flirty layered hem, it’s basically a love letter in dress form.
Fit & Features
- Flocked floral pattern, mesh-lined fabric
- Strapless sweetheart neckline, padded bra cups
- Corset-inspired bodice
- Back zipper and hook-eye closure
- Form-hugging fit
- Tiered ruffle mini-length hem
- Runs true to size
Style Number/Barcode: 05101-001053
Category Name: Casual Dresses
Price: $59.90
Availability: In Stock
Available Color: IVORY-2
Available Size: L
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All Eyes On You Strapless Maxi Dress
Effortlessly sleek, this strapless maxi is giving luxe with zero effort. The body-hugging fit and flowy hem make it your go-to for dinner dates or rooftop hotel bars.
Fit & Features
- Rib knit stretchy fabric
- Strapless neckline
- Bodycon fit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 06005-000088
Category Name: Casual Dresses
Price: $12.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Through The Meadow Floral Corset Dress
Too sweet to scroll past. This corset floral dress brings all the cottagecore charm with a flirty twist—yes, that oversized bow is doing the most. Perfect for shower celebrations or dressy events!
Fit & Features
- Floral print, woven texture fabric, lace trim woven lining
- Sweetheart lace trim neckline, bust tie
- Adjustable shoulder straps
- Corset bodice, flexible boning inserts, lace trim
- Back bow tie, zipper and hook-eye closure
- Drop waist seam, skater short-length silhouette
- Runs true to size
Style Number/Barcode: 05101-000269
Category Name: Casual Dresses
Price: $9.97 $62.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sunkissed Curve Knit Midi Dress
This striped midi dress was made to highlight every curve with a sculpting rib texture, front cutout detail, and side slit. Dress it up with heels for a night out or keep it elevated with sandals for a chic daytime moment.
Fit & Features
- Striped print, rib knit fabric
- Sweetheart neckline, cutout bust accent
- Adjustable spaghetti straps
- Bodycon fit
- Dual side slits
- Midi-length hem
- Runs true to size
Style Number/Barcode: 06005-000084
Category Name: Casual Dresses
Price: $6.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Effortlessly Chic Ribbed Knit Skater Dress
When your outfit says polished but still playful, this is the skater dress. The mock neck and fit-and-flare silhouette keep it chic, flirty, and ready for any plans on your calendar.
Fit & Features
- Ribbed sweater knit fabric, moderate stretch
- Sleeveless mock neckline
- Tank shoulder straps
- Short skater silhouette
- Runs true to size
Style Number/Barcode: 06005-000085
Category Name: Casual Dresses
Price: $15.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Bloom Season Floral Mesh Maxi Tube Dress
Meet your new obsession for dinner dates and chic soirées. This floral mesh maxi dress hugs in all the right places with a strapless neckline that feels effortlessly elevated.
Fit & Features
- Sheer mesh fabric with knit lining, high stretch
- Floral print
- Strapless straight-across neckline
- Ruching
- Maxi-length hem, back slit
- Form-hugging silhouette
- Runs true to size
Style Number/Barcode: 05101-000252
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Laced In Love Corset Mini Dress
She’s giving drama, curves, and just the right amount of trouble. This corset mini dress hugs you in all the right places with a flirty ruffle that finishes the look with a wink.
Fit & Features
- Lace fabric, stretchy knit lining
- Strapless sweetheart neckline
- Built-in underwire padded but
- Corset bodice, flexible boning, back zipper and hook-eye closure
- Form-hugging fit
- Ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05101-000256
Category Name: Casual Dresses
Price: $20.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Dreamy Romance Floral Lace Skater Dress
Sweet? Always. Innocent? Rarely. This lace mini gives flirty vintage feels with a neckline made to be noticed and a hem made to be twirled.
Fit & Features
- Floral print, lace fabric, stretchy knit lining
- Adjustable spaghetti straps
- Ruched square neckline
- Skater silhouette, drop waist seam
- Flared mini-length hem
- Runs true to size
Style Number/Barcode: 05101-000240
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Whirlwind Romance Floral Abstract Maxi Dress
This maxi dress is giving goddess in the wild. The sheer mesh and abstract floral print bring soft drama to any scene, whether it's brunch or rooftop party soirees!
Fit & Features
- Abstract floral print, mesh lined fabric
- Sweetheart neckline, padded bra cups, ruched bust seam
- Spaghetti straps
- Curve-hugging maxi silhouette
- Runs true to size
Style Number/Barcode: 05101-000242
Category Name: Casual Dresses
Price: $7.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Vacation Booked Floral Maxi Dress
Already picturing the dinner plans in this one. This tropical floral maxi dress features a soft cowl neckline and an open back that brings just the right amount of drama for your getaway lineup.
Fit & Features
- Tropical floral print, mesh-lined fabric, high stretch
- Cowl neckline
- Adjustable spaghetti straps
- Open strappy back
- Form-hugging fit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000189
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Darling Babe Striped Drop Waist Skater Dress
So darling, this striped woven skater dress is effortless perfection. The sleeveless square neckline is accented with a mini bow detail, and the drop waist design leads to a pleated fit-and-flare silhouette.
Fit & Features
- Striped woven fabric
- Sleeveless square neckline, eyelet trim, mini bow detail
- Tank shoulder straps
- Square back, zipper closure
- V-shaped drop waist
- Short pleated skater silhouette
- Runs true to size
Style Number/Barcode: 05102-000145
Category Name: Casual Dresses
Price: $10.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Off-Duty Icon Mock Neck Mini Dress
A sleek mock neck and bodycon ruched silhouette keep your fit snatched from every angle, while the abstract print brings chic energy to your next date night or rooftop dinner.
Fit & Features
- Abstract print, mesh-lined fabric
- Mock neck
- Ruched bodycon silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000188
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sunshine Cutie Strapless Ruffle Eyelet Mini Dress
Created for the cuties, this eyelet mini dress is a cute look for shower celebrations or casual parties! Designed to hug your form for a flattering fit, the strapless neckline and ruffled mini hem add a flirty and playful touch.
Fit & Features
- Eyelet fabric, stretchy knit lining
- Strapless neckline
- Form-hugging fit
- Ruffled layer mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000187
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Once Upon This Corset Skater Dress
Whimsy in every stitch. With lace trims, corset details, and a floaty mini hem, this skater dress feels like it was made for fairy tales, flower fields, and falling in love (again).
Fit & Features
- Cotton-blend woven fabric
- Multiple petticoat tulle and lace trim woven linings
- Strapless lace trim drawstring tie square neckline
- Hidden side zipper and hook-eye closure
- Corset bodice, flexible boning, lace and pleated trims, back lace-up placket
- Drop waist seam, voluminous skater silhouette, mini-length hem
- Runs true to size
Style Number/Barcode: 05101-000229
Category Name: Casual Dresses
Price: $69.90
Availability: Out of Stock
Product Badge:- Ships Free
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Casual Fave Flowy V-Neck Midi Dress
This breezy lightweight midi dress will be your new casual fave for weekend plans. Designed with a sleeveless V-neck, low back, and mid-length flowy fit, style with a layered necklace and strappy sandals.
Fit & Features
- Gauze woven fabric, mini-length stretchy knit lining
- Sleeveless V-neckline
- Adjustable spaghetti straps, low back
- Hidden side pockets
- High side slit
- Midi-length flowy silhouette
- Runs true to size
Style Number/Barcode: 05102-000185
Category Name: Casual Dresses
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Gorgeous Vibe Floral Bodycon Mini Dress
Radiate a gorgeous vibe in this bold floral print mini dress designed with a strapless neckline and bodycon silhouette to flaunt your curves.
Fit & Features
- Smooth knit fabric with knit lining, high stretch
- Large floral print
- Strapless straight neckline, no-slip strip
- Mini-length hem
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000147
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Bubbly and Booked Striped Collar Dress
For the girl with plans, lattes, and an effortless look. This striped dress keeps it crisp with a collar button-down design and a bubble hem that adds a little bounce to every step.
Fit & Features
- Striped print, cotton fabric, sewn-in woven lining
- Collared neckline
- Button-down closures
- Belted waist
- Bubble short hem
- Runs true to size
Style Number/Barcode: 05102-000182
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Hot Glow Denim Western Mini Dress
Bold lines, bold moves. This strapless bodycon mini dress features standout topstitch detailing and a daring front cutout that sculpts your curves and keeps all eyes on you.
Fit & Features
- Denim fabric, slight stretch, Western flame stitched design
- Strapless sweetheart wired neckline, padded bra cups
- Front keyhole cutout
- Back zipper and hidden button-up closures
- Bodycon silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000181
Category Name: Casual Dresses
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Alluring Bloom Flocked Floral Mesh Maxi Dress
This dress is giving sultry garden goddess. The strapless neckline and body-hugging mesh silhouette keep it sleek, while the flocked floral detail adds just the right amount of romance. Perfect for whenever you want to turn a subtle moment into the moment.
Fit & Features
- Sheer mesh fabric with knit lining, high stretch
- Flocked floral print pattern
- Strapless straight-across neckline
- Back zipper closure
- Ruching
- Fitted silhouette, midi-length flared hem
- Runs true to size
Style Number/Barcode: 05101-000180
Category Name: Casual Dresses
Price: $24.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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So Sweet Floral And Plaid Patchwork Mini Dress
Create the perfect weekend look in this oh-so-sweet mini dress designed with a floral and plaid patchwork pattern. The crochet bust trim and tie-front detail are dainty details you'll adore.
Fit & Features
- Woven fabric, no stretch
- Ditsy floral and plaid patchwork pattern
- Sleeveless sweetheart neckline, crochet trim and tie-front detail, ruched bust
- Adjustable spaghetti straps
- Hidden back zipper, hook-eye closure
- Mini-length hem, fitted A-line silhouette
- Runs true to size
Style Number/Barcode: 05101-000178
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Ruffle Repeat Lace Tube Mini Dress
She’s sleek up top, party on the bottom—aka your new go-to for nights that need a little extra twirl. The strapless neckline and tiered ruffles make it an easy yes for going out.
Fit & Features
- Lace fabric, stretchy knit lining
- Strapless tube neckline
- Form-hugging fit
- Ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05101-000171
Category Name: Casual Dresses
Price: $9.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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That Girl Energy Cutout Tube Midi Dress
Steal the scene and leave them speechless. This sleek strapless midi hugs your curves with a smooth, sculpted fit perfect for date nights, parties, or whenever you’re feeling that girl energy.
Fit & Features
- Brushed knit soft fabric, knit lining, moderate stretch
- Strapless tube neckline
- Cutout back, lower ruched seam
- Bodycon silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-000176
Category Name: Casual Dresses
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Twirl Season One-Shoulder Skater Mini Dress
A little flirty, a little playful. This dress boasts a flattering skater silhouette and an off-shoulder neckline, making it made for cute date nights and celebrations!
Fit & Features
- Sweater knit fabric, moderate stretch
- Asymmetrical one-shoulder neckline
- Skater silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 06005-000079
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free