Work Dresses & Outfits
Elevate your professional wardrobe with our sophisticated collection of work dresses, perfect for speaking presentations to business casual days. Our selection is tailored to meet the demands of the modern workplace, ensuring you find the ideal dress to showcase your style and professionalism. Opt for a refined crepe midi dress that exudes elegance and grace, ideal for important meetings or a day at the office. For a more contemporary twist, explore our sweater dresses, blending classic style with modern comfort. Whether you're presenting in the boardroom or networking at a business luncheon, our work dresses are designed to make a statement, balancing the perfect blend of sophistication, functionality, and style
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Workwear Dresses for the Office, Conference, or Meeting
Refresh your work wardrobe with our latest collection of spring-ready workwear dresses, designed to keep you polished, comfortable, and effortlessly stylish. Whether you're heading into the office, attending an industry conference, or meeting clients over lunch, our work dresses offer the perfect balance of sophistication and versatility for a seamless day-to-night transition.
Embrace Light & Breezy Fabrics for Spring
This season, refresh your professional look with midi dresses in breezy chiffon, soft crepe, and lightweight knit—perfect for a polished yet effortless aesthetic. These midi styles elongate your silhouette while offering a refined below-the-knee length that’s ideal for your workday. Style a sleeveless midi dress with a tailored blazer and sleek point-toe heels for a crisp, professional ensemble.
Layer with Chic Spring Staples
As the season transitions, layer up with a lightweight cardigan over a fresh floral or abstract print dress and finish the look with classic block-heel sandals for a polished, feminine touch. For a modern business casual vibe, pair a ribbed knit midi dress with a structured denim jacket and neutral-toned mules for an effortless blend of comfort and sophistication. These midi-length work dresses from Windsor make everyday styling effortless.
From Work to After-Hours in Style
Knit and lightweight sweater dresses are perfect for both the nine-to-five grind and after-work plans. These versatile pieces can take you from your desk to dinner with ease—simply swap out your blazer for a sleek faux leather moto jacket and add statement earrings for a polished evening look.
Step into spring with confidence in Windsor’s latest collection of workwear dresses that keep you looking chic and professional. Discover the newest styles online or visit your nearest Windsor store today!
How can I style a dress for work?
You can style your work dresses with layers, statement and minimal jewelry, and chic footwear. Starting with layers, you can layer your workwear dress with structured or boyfriend blazers to elevate your business casual look. You can style your blazer by rolling the sleeves up to a quarter length, then adorn your look with dainty chain link bracelets. For your sleeveless dresses that may not be work-appropriate when worn alone, you can style these dresses with long sleeve tops or collared blouses underneath to refresh your sleeveless dresses for work. Another chic layering option could be styling your tie-front tops over your sleeveless or strapless dresses. Be sure to choose a pattern that compliments your dress. Avoid clashing by pairing prints with muted colors to create a seamless contrast that goes together. Be sure to add accessories like statement necklaces, dainty chain-link necklaces, versatile hoops, and studs that elevate your workwear outfits. For your footwear, you can style your dress with sturdy mules, block heels, or ankle booties that are comfortable enough to wear all day but give your dresses a stylish feel—avoid wedges and sandals that may be deemed too casual for the workplace.
How do I know if my dress is ok to wear at work?
The best way to know if your dress is ok to wear at work is to consult your employee handbook to gauge whether your outfit is in line with the dress code. Now if your handbook isn’t explicitly clear on the dress code, a good rule of thumb would be to dress business casual or err on the side of classic and accessible. For the fabrication choose dresses that come in durable fabrications like ribbed knit, Ponte knit, and crepe—avoid sheer fabrics that can reveal more than you’d like to at work. For example, it’s best to not have any spaghetti straps, strapless styles, or halter dresses without another layer. That’s where sweaters and blazers as layering pieces come in handy to make sure your dress is work-appropriate. In addition, you should also think about the length of your dress and how tight it is. If it seems more club-appropriate than work-appropriate, it’s best to leave it at home and reach for a classic shift dress instead. The bottom line is that you want to look professional in all that you do in your career or that part-time gig, and wearing a work-appropriate dress sends just that message.
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Floral Fever Ribbed Knit Mini Dress
Keep it stylish with a floral dress that is all the rage! The dress features a sleeveless sweetheart neckline, spaghetti straps, a tie-front at the bust, a ditsy floral print, and a mini-length silhouette. The dress is composed of a ribbed knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with wedges.
Fit & Features
- Sleeveless sweetheart neckline
- Spaghetti straps
- Tie-frontÂ
- Ditsy floral printÂ
- Mini-length silhouetteÂ
- Ribbed knit fabric, form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-2032
Category Name: Work Dresses & Outfits
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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RSVP To Cute Ditsy Wildflower Tie A-Line Midi Dress
RSVP yes to shower or birthday invites when you have this cute ditsy wildflower tie A-line midi dress in your closet! Embellished with a ditsy wildflower print, this midi-length dress is sure to turn heads. With short puff sleeves and a square neckline, this dress is perfect for casual-dressy occasions. The tie front bust adds a touch of whimsy while the a-line silhouette and front slit provide movement and a flattering look. Complete the look with luxe earrings and tennis shoes.
Fit & Features
- Ditsy wildflower print
- Woven fabric lined with stretchy knit
- Tie front bust, back zipper and hook-eye closure
- Front slit
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05101-3008
Category Name: Work Dresses & Outfits
Price: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Fresh Lines Sleeveless Pinstripe Mini Tube Dress
Look fresh this season in this strapless pinstripe mini dress boasting a sleek bodycon silhouette and faux front pockets. Pair with chic flats.
Fit & Features
- Woven knit fabrication
- Sleeveless square neckline
- Pinstripe pattern
- Faux front pockets
- Mini length hem
- Runs true to size
Style Number/Barcode: 05102-5963
Category Name: Work Dresses & Outfits
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Wild And Chic Zebra Print Mini Sweater Dress
Add a wild flair to your everyday look with this chic zebra print sweater dress. It features a sleeveless V-neckline, halter straps with a tie-back design, an open back, a mini-length hem, and a curve-hugging fit. The sweater knit fabric offers a moderate stretch. Style with a mini handbag and clear mules for a fashion-forward look.
Fit & Features
- Sleeveless V-neckline
- Halter straps, tie-back design
- Open back
- Mini-length hem
- Curve-hugging silhouette
- Zebra print, sweater knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1699
Category Name: Work Dresses & Outfits
Price: $3.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Casual Chic Icon Long Sleeve Knit Midi Dress
Become an instant chic icon in this bodycon midi dress adorned with flare cuff long sleeves with flirty tie accents and a V-neckline. Pair with mules.
Fit & Features
- Lined brushed knit fabric, plenty of stretch
- V-neckline
- Long fitted sleeves with ruched slit flare accents, adjustable drawstrings
- Midi-length bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5895
Category Name: Work Dresses & Outfits
Price: $9.97 $38.90
On Sale: Yes
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
Product Badge:- Sale
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Feeling Good Turtleneck Maxi Dress
Look and feel good in this rib knit maxi dress perfect for everyday styling! It features long sleeves, a turtleneck, a form-hugging silhouette, and a side-slit accent. Complete the look in mules for a dinner date.
Fit & Features
- Long fitted sleeves
- Turtleneck
- Form-hugging silhouette
- Side slit
- Maxi-length hem
- Rib-knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4861
Category Name: Work Dresses & Outfits
Price: $5.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Cute In The City V-Neck Knit Midi Dress
You'll be looking cute in the city in this casual midi dress perfect for a dinner date! It features bell long sleeves, a front and back V-neckline, and a flattering bodycon silhouette on rib knit fabric with a sewn-in knit lining. Complete the look with a chic crossbody bag.
Fit & Features
- Rib knit fabric, sewn-in knit lining
- Moderate stretch
- Bell long sleeves
- Front and back V-neckline
- Bodycon silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-5192
Category Name: Work Dresses & Outfits
Price: $19.97 $33.90
On Sale: Yes
Availability: Out of Stock
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High Intentions Sleeveless Knit Mini Dress
Take your wardrobe to the next level in this little black dress perfect for day or night plans! This mini dress boasts a sleeveless high square neckline and spaghetti straps for a chic and modern look. The bodycon silhouette hugs your curves, while the mini-length hem adds a touch of flirtatiousness. The lightweight knit fabric offers a moderate stretch. Complete the look in a trendy crop jacket, mules, and a purse!
Fit & Features
- Knit fabric with moderate stretch
- High square neckline
- Spaghetti straps
- Bodycon fit
- Runs true to size
Style Number/Barcode: 06005-1881
Category Name: Work Dresses & Outfits
Price: $6.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Brunch Date Floral Chiffon Skater Dress
This adorable floral chiffon skater dress is perfect for brunch dates! The mini dress features a sleeveless square neckline, spaghetti straps, a smocked bust, a short skater skirt with a fit and flare silhouette, and a dainty floral print pattern, this dress is a must-have for the spring and summer seasons. Style with heeled sandals.
Fit & Features
- Sleeveless square neckline, spaghetti straps
- Smocked bust
- Short skater skirt, fit and flare silhouette
- Dainty floral print
- Swiss dot chiffon fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05101-2282
Category Name: Work Dresses & Outfits
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Polished Perfection Vest Pleated Short Dress
Capture polished perfection in this chic vest pleated short dress! Designed with a structured twill woven fabric, this dress features a fitted vest top with an A-line skirt. The top is shaped with a sleeveless V-neckline and tank shoulder straps, followed by a button-front design and an angled cropped hem for a snatched look. The chic waist cutout adds a touch of allure, leading to a fitted high waist and a flowy, pleated short-length hem. The dress includes a back zipper closure for effortless styling. Complete your look with gold hoops and strappy mules!
Fit & Features
- Non-stretch twill woven fabric
- Sleeveless V-neckline with tank shoulder straps
- Button-front design, angled cropped hem
- Back zipper with hook and eye closure
- Waist cutout, high-rise skirt with pleating
- A-line fit
- Runs true to size
Style Number/Barcode: 05102-5536
Category Name: Work Dresses & Outfits
Price: $5.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Back To Basics Ribbed Knit Midi Dress
Every girl needs this basic ribbed knit midi dress in her line up! The dress features a classic crew neckline and short sleeves perfect for layering with a sweater or jacket and a form-hugging fit.
Fit & Features
- Ribbed knit fabric with brushed knit lining, plenty of stretch
- Crew neckline
- Short sleeves
- Midi-length hem
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 05102-5603
Category Name: Work Dresses & Outfits
Price: $28.90
Availability: In Stock
Available Color: CHARCOAL
Available Size: XS, S, M, L
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Irresistible Romance Rose Velvet Lace Midi Dress
Who can resist your romantic allure in this rose velvet midi dress? It features a sleeveless sweetheart neckline with a sheer lace trim, sleek bungee spaghetti straps, a curved underbust seam, a bodycon silhouette, and a back-slit accent. The mid-length dress is composed of a flocked velvet rose pattern on sheer mesh fabric with a stretchy knit lining. Complete the look in chic stiletto mules for a cocktail party or rehearsal dinner!
Fit & Features
- Sleeveless sweetheart neckline, sheer lace trim
- Bungee spaghetti straps
- Curved underbust seam
- Bodycon silhouette
- Midi-length hem, back slit accent
- Rose flocked velvet pattern, sheer mesh fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05101-3544
Category Name: Work Dresses & Outfits
Price: $46.90
Availability: In Stock
Available Color: BURGUNDY
Available Size: XS, S
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Trendy Topic Strapless Denim Midi Dress
You'll be the topic of conversation in this denim midi dress for the trendiest look at casual hangs or brunch! This stunning denim dress features a strapless neckline and a form-hugging silhouette that will accentuate your curves. The belt loop accents and four-pocket styling add cute functional details, while the front center slit and midi-length hem provide a modern touch. Complete the look in sleek hoop earrings and pumps!
Fit & Features
- Denim fabric with minimal stretch
- Belt loops, four-pocket styling
- Front center slit
- Side zipper closure
- Form-hugging silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-5455
Category Name: Work Dresses & Outfits
Price: $9.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Charming Mood Collared Woven Skater Dress
Charm them all with your chic style in this sleeveless collared skater dress! Designed with a lightweight woven fabric, this short dress features a collared V-neckline and a flirty open back. The button-front design goes down the complete length of the dress for effortless styling. The high waist is accented with a wide belt for a cinched look, leading to the fit and flare skater silhouette. Complete the look for a spring party with clear heels.
Fit & Features
- Non-stretch lined woven fabric
- Sleeveless collared V-neckline, open back
- Button-down front
- High belted waist with circular buckle
- Skater silhouette
- Sticky bra recommended
- Runs true to size
Style Number/Barcode: 05101-3346
Category Name: Work Dresses & Outfits
Price: $6.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweet Vibes Collared Striped Woven Skater Dress
Sweet and stylish, this striped woven skater dress is spring-time perfection! The lightweight woven fabric features a chic vertical striped pattern for a polished look. The short dress has a collared V-neckline for that touch of sophistication, leading to a partial button-down front. The short puff sleeves add an adorable detail. The high waist is accented with a tie-back design, and flows out to a fit-and-flare skater silhouette. Pair this short dress with wedges for weekend brunch!
Fit & Features
- Non-stretch cotton-blend woven fabric, woven skirt lining
- Vertical striped pattern
- Collared V-neckline, button-down front
- Short puff sleeves with elastic cinched hems
- High waist with back elastic band, tie-back design
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05102-5657
Category Name: Work Dresses & Outfits
Price: $6.97 $56.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Perfect And Stylish Scoop Neck Ribbed Knit Midi Dress
Perfect and stylish for everyday occasions, this basic ribbed knit midi dress is just what you need for coffee dates, shopping downtown, or grabbing dinner with friends! This stunning dress features classic short sleeves, a flattering scoop neckline, and a bodycon silhouette for a sleek curve-flaunting appeal. The side slit offers movement along the mid-length hem, while the soft and stretchy ribbed knit fabric ensures all-day comfort. Style this midi dress with a casual jacket, sandals, and a crossbody bag to complete the look!
Fit & Features
- Soft, stretchy ribbed knit fabric
- Side slit
- Bodycon silhouette
- Midi-lengthÂ
- Runs true to size
Style Number/Barcode: 05102-5554
Category Name: Work Dresses & Outfits
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Compliment Me High Slit Knit Midi Dress
You'll spark up all the compliments in this simply chic high slit midi dress! Designed with a stretchy structured knit fabric, this dress is shaped with a sleeveless square neck and back with thin tank shoulder straps. The mid-length hem is accented with a high-cut side slit to show off some leg, and the bodycon silhouette will flaunt your stunning curves. Style with a faux leather jacket and heels to go bar-hopping!
Fit & Features
- Stretchy structured knit fabric
- Sleeveless square neck and back
- Tank shoulder straps
- High side slit
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5526
Category Name: Work Dresses & Outfits
Price: $5.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Preppy-Chic Belted And Pleated Skater Dress
 This preppy-chic twill skater dress features a collared neckline with a partial button-down front, short cap sleeves, and a subtle drop waist with a belted design. The mini-length pleated skater fit adds that flirty touch to the short silhouette.
Fit & Features
- Twill woven fabric, slight stretch
- Collared neckline, button-down front
- Cap sleeves
- Belted drop waist
- Mini-length pleated skater silhouette
- Runs true to size
Style Number/Barcode: 05102-5915
Category Name: Work Dresses & Outfits
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
- Twill woven fabric, slight stretch
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Living A Dream Marble Off-The-Shoulder Midi Dress
This dreamy mesh midi dress is ready for you to take on any event! The stylish marble mesh fabric is sure to make a dramatic statement with its off-the-shoulder neckline, ruched fitted sheer long sleeves, flattering side ruched seams, and bodycon silhouette. Complete the look in stiletto heels for a birthday dinner or date night!
Fit & Features
- Off-the-shoulder neckline
- Ruched fitted sheer long sleeves
- Side ruched seams
- Bodycon silhouette
- Midi-length hem
- Marble print, mesh fabric, sewn-in knit lining
- Runs true to size
Style Number/Barcode: 05102-5332
Category Name: Work Dresses & Outfits
Price: $19.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Check It Plaid Mini Skirt With Suspenders
Check this plaid mini skirt into your weekly lineup! Featuring a mid-rise waist with suspender straps with tie closure, a bodycon silhouette, and a flirty slit along the hem. Style with a basic tee and boots for a cute complete look!
Fit & Features
- Mid-rise waist
- Suspender straps with tie closure
- Bodycon silhouette
- Front slit, mini-length hem
- Plaid pattern, texture knit fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06501-0970
Category Name: Work Dresses & Outfits
Price: $10.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Good Looks Mock Neck Long Sleeve Knit Midi Dress
This mock neck midi dress will look so good on you! The midi dress features fitted long sleeves, a flattering form-hugging fit, and a center back slit on soft and stretchy ribbed knit fabric. Complete the look with a moto jacket for day or evening plans!
Fit & Features
- Soft and stretchy ribbed knit fabric
- Mock neckline
- Fitted long sleeves
- Form-hugging fit
- Center back slit
- Runs true to size
Style Number/Barcode: 05102-5221
Category Name: Work Dresses & Outfits
Price: $19.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Resort Babe Distressed Sweater Mini Dress
A chic sweater mini dress that'll have you dreaming of your next getaway plans or sunny adventure! The mini-length dress is designed with fitted long sleeves, a crew neckline, a flattering bodycon silhouette, trendy side cutout accents to show a peak of skin and an asymmetrical hem on distressed soft sweater knit fabric. Complete the look in clear sandals and a handbag!
Fit & Features
- Fitted long sleeves
- Crew neckline
- Bodycon silhouette
- Side cutout accents
- Asymmetrical mini-length hem
- Distressed soft sweater knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1837
Category Name: Work Dresses & Outfits
Price: $6.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Things To Do Ponte Plaid Blazer Dress
You've got things to do and this ponte plaid blazer mini dress will keep you chic throughout the day! Designed with a trendy glen plaid print, this mini blazer dress features long sleeves, a lapel collar neckline, double-breasted button closures, faux pockets, and a form-hugging fit. Complete the look in knee-high boots and a purse!
Fit & Features
- Long sleeves
- Lapel collar neckline
- Double-breasted button closures
- Form-hugging fit
- Mini-length hem
- Glen plaid print, ponte fabric, slight stretch
- Runs true to size
Style Number/Barcode: 06204-1684
Category Name: Work Dresses & Outfits
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Highly Selective Choker Neck Sweater Midi Dress
Highly sophisticated and selective, this off-the-shoulder sweater midi dress is an exquisite piece for any occasion! It features a choker neckline, fitted long sleeves, and a bodycon and midi-length hem to ensure you look polished and elegant. Complete the look in booties for dinner and drinks!
Fit & Features
- Off-the-shoulder, choker neckline
- Fitted long sleeves
- Bodycon silhouette
- Midi-length hem
- Sweater ribbed knit fabric
- Moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1897
Category Name: Work Dresses & Outfits
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance