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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Chic Night Out Abstract Print Mesh Midi Dress
Create a chic vibe to grab drinks with the girls in this airy mesh midi dress designed with a bold abstract print pattern. The dress features a sleeveless mock neckline, tank shoulder straps, ruching at the waist, and a bodycon silhouette to flaunt your curves.
Fit & Features
- Sheer mesh fabric with brushed knit lining, plenty of stretch
- Abstract print
- Mock neckline
- Tank shoulder straps
- Ruched waist
- Midi-length bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5929
Category Name: Work Dresses & Outfits
Price: $34.90
Availability: In Stock
Available Color: OLIVE
Available Size: XS, S
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So Irresistible Mesh Midi Dress
You'll be a vision in this simply irresistible mesh midi dress perfect for an engagement party or cocktail soiree! It features a sleeveless plunge v-neck, adjustable straps, a back slit accent, and ruched seams that accentuate your curves along the bodycon silhouette. Complete the look in stiletto heels.
Fit & Features
- Sleeveless plunge v-neck
- Adjustable spaghetti straps
- Back zipper and hook-eye closure
- Ruched seams, back slit accent
- Bodycon, midi-length hem
- Mesh fabric, sewn-in knit lining, minimal stretch
- Fits true to size
Style Number/Barcode: 05101-1857
Category Name: Work Dresses & Outfits
Price: $19.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Modern Stripes Ribbed Knit Long Sleeve Mini Dress
Capture a modern vibe in this striped rib knit long sleeve mini dress designed with a chic mock neck and flattering bodycon fit. Pair with boots.
Fit & Features
- Ribbed knit fabrication
- Mock neck
- Fitted long sleeves
- Multi-stripe pattern
- Mini length hem
- Runs true to size
Style Number/Barcode: 06005-2095
Category Name: Work Dresses & Outfits
Price: $16.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Wear Your Art Striped Midi Dress
Wear this fine work of art and every eye will be on you! This marble striped midi dress features long sleeves, front and back v-necklines, a bodycon silhouette, and a tie-front waist. Complete the look in PVC mules for a casual lunch!
Fit & Features
- Long sleeves
- Front and back v-necklines
- Bodycon silhouette
- Tie-front waist
- Midi-length hem
- Marble striped print, stretch-knit fabric
- Fits true to size
Style Number/Barcode: 05102-4821
Category Name: Work Dresses & Outfits
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Casual Affair Long Sleeve Ruched Midi Dress
Make a casual-chic impression in this long sleeve ruched midi dress showcasing a folded off-the-shoulder neckline and a bodycon silhouette. Pair with heels.
Fit & Features
- Smooth knit fabrication, moderate stretchÂ
- Off-the-shoulder neckline, foldover accent
- Fitted long sleeves
- Ruching
- Midi length hem
- Runs true to size
Style Number/Barcode: 05101-3723
Category Name: Work Dresses & Outfits
Price: $39.90
Availability: In Stock
Available Color: BROWN, WINE
Available Size: S, M, L
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Only The Best Cutout Sweater Dress
Treat yourself to the best sweater midi dress to have this season! It features fitted long sleeves, an asymmetrical neckline with contrast trim, a form-hugging silhouette, and a flirty side waist cutout with contrast trim. Style with block heels to complete the look!
Fit & Features
- Fitted long sleeves
- Asymmetrical neckline, contrast trim
- Form-hugging silhouette
- Side waist cutout, contrast trim
- Midi-length hem
- Rib-knit sweater fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1639
Category Name: Work Dresses & Outfits
Price: $6.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Chic Fall Vibe Ditsy Floral Corset Midi Dress
Channel the chic fall vibe in this ditsy floral woven midi dress featuring a sleeveless sweetheart neckline with a ruched bust and tie-front detail, thin tank shoulder straps, and a corset-style bodice. The high waist leads to a flowy A-line silhouette accented with a high-cut front slit.
Fit & Features
- Ditsy floral-printed woven fabric
- Sweetheart neckline, ruched bust, tie-front detail, underwire bust
- Thin tank shoulder straps
- Corset-style bodice with piping, high waist seam
- Hidden side zipper and hook-eye closure
- High front slit
- Midi-length A-line fit
- Runs true to size
Style Number/Barcode: 05101-3706
Category Name: Work Dresses & Outfits
Price: $46.90
Availability: In Stock
Available Color: BROWN
Available Size: S
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Classic And Sleek Knit Off-Shoulder Long Sleeve Midi Dress
Classic and sleek, this stretchy knit midi dress features an asymmetric off-shoulder neckline with long fitted sleeves, ruching at the waist to accentuate your curves, and a bodycon silhouette. Style with stiletto heels for a chic outing!
Fit & Features
- Jersey knit fabric with plenty of stretch
- Asymmetric off-shoulder neckline
- Long fitted sleeves
- Ruched waist
- Midi-length bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5977
Category Name: Work Dresses & Outfits
Price: $19.97 $24.90
On Sale: Yes
Availability: Out of Stock
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Sleek Silhouette Ribbed Knit Off-The-Shoulder Midi Dress
Showcase a sleek silhouette in this ribbed knit midi dress featuring an off-the-shoulder neckline with a fold-over design and a mermaid silhouette to highlight your curves. Style with knee-high boots for a chic look.
Fit & Features
- Ribbed knit fabric, plenty of stretch
- Off-the-shoulder neckline
- Fold-over design, short sleeves
- Midi-length mermaid silhouette
- Runs true to size
Style Number/Barcode: 05102-5896
Category Name: Work Dresses & Outfits
Price: $14.97 $44.90
On Sale: Yes
Availability: In Stock
Available Color: BROWN
Available Size: XS, S
Product Badge:- Sale
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Chic Girl Flocked Mesh Mock Neck Midi Dress
Create a chic look for a rooftop party in this sheer mesh midi dress designed with a floral velvet flocked pattern that will turn heads. It features a sleeveless mock neckline, tank shoulder straps, and ruched side seams to accentuate your curves along the bodycon silhouette.
Fit & Features
- Sheer mesh fabric with floral velvet flocked pattern, knit lining
- Mock neckline
- Tank shoulder straps
- Back zipper closure
- Ruched side seams
- Midi-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05101-3567
Category Name: Work Dresses & Outfits
Price: $44.90
Availability: In Stock
Available Color: GRAY
Available Size: XS, S, M, L
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Steal The Spotlight Leopard Slit Midi Dress
Steal the spotlight looking so fierce in this leopard midi dress! It features a sleeveless V-neckline, spaghetti straps, a flowy midi-length hem, and a front slit perfect for showing off some skin. Style with a pair of strappy sandals.
Fit & Features
- Sleeveless V-neckline
- Spaghetti straps
- Midi-length hem, flowy silhouette
- Front slit
- Leopard print
- Crepe knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4306
Category Name: Work Dresses & Outfits
Price: $19.97 $37.90
On Sale: Yes
Availability: Out of Stock
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Standout Staple Crew Neck Cutout Midi Dress
This midi dress may just become that special staple piece in your lineup! It features fitted long sleeves, a crew neck with a button-back closure and keyhole accent, a flattering bodycon silhouette and front slit, and a flirty cutout back design. Complete the look with statement earrings for a cocktail hour.
Fit & Features
- Fitted long sleeves
- Crew neck, back button closure, keyhole
- Bodycon silhouette, front slit
- Cutout back design
- Soft knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5335
Category Name: Work Dresses & Outfits
Price: $24.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
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Endlessly Effortless Crew Neck Abstract Midi Dress
You'll always look and feel perfect in this sleeveless midi dress for parties or going out! Crafted from an abstract print mesh fabric, this dress boasts a crew neckline, a flattering bodycon silhouette, and a midi-length hem. Complete the look in stiletto heels and a purse!
Fit & Features
- Abstract print, mesh fabric, soft knit lining
- Crew neckline
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-5819
Category Name: Work Dresses & Outfits
Price: $19.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Plaid Moment Sleeveless Knit Romper
Fit & Features
- Plaid printed woven knit fabrication with minimal stretch
- Strapless straight neckline, no-slip strip
- Flexible boning, back zipper with hook-eye closure
- Mini skirt length front overlay, dual side slits
- Cheeky shorts
- Romper in size small is 23" top hem to bottom hem with a 12" front rise and a 3" inseam
- Runs true to size
Style Number/Barcode: 06403-0627
Category Name: Work Dresses & Outfits
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
- Plaid printed woven knit fabrication with minimal stretch
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Flirty Expression Sleeveless Plaid Mini Dress
A sleeveless plaid mini dress features a flattering square neckline with a satin bow, shoulder straps, and a bodycon silhouette. Perfect for back-to-school styling.
Fit & Features
- Plaid woven fabric, bust lining, minimal stretch
- Square neckline with satin bow
- Shoulder straps
- Bodycon mini-length silhouette
- Runs true to size
Style Number/Barcode: 05102-5825
Category Name: Work Dresses & Outfits
Price: $19.97 $39.90
On Sale: Yes
Availability: Out of Stock
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Chic Trendsetter Knit Chiffon Drop Waist Midi Dress
This trendy midi dress features a sleeveless mock neckline, tank shoulder straps, and a V-shaped drop waist design. The midi-length A-line silhouette is accented with a shirred sheer chiffon overlay for an effortlessly chic look.
Fit & Features
- Smooth knit lined fabric
- Mock neckline, tank shoulder straps
- Back zipper closure
- V-shaped drop waist
- Sheer chiffon overlay with shirring
- Midi-length A-line silhouette
- Runs true to size
Style Number/Barcode: 05101-3691
Category Name: Work Dresses & Outfits
Price: $11.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Carefree Chic Long Sleeve Ribbed Knit Midi Dress
An off-the-shoulder midi dress perfect for those carefree days! It features fitted long sleeves and a bodycon fit that shows off your curves. Pair with sneakers.
Fit & Features
- Ribbed knit fabrication, stretchy knit lining
- Off-the-shoulder neckline
- Fitted long sleeves
- Midi length hem
- Runs true to size
Style Number/Barcode: 05102-5924
Category Name: Work Dresses & Outfits
Price: $9.97 $38.90
On Sale: Yes
Availability: In Stock
Available Color: DARK, MARSALA
Available Size: S, M, L
Product Badge:- Sale
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Casual Luxe Long Sleeve Ribbed Knit Mini Dress
Part casual, part luxe, this long-sleeved mini dress is perfect for your next date night! The ribbed knit dress features a square neckline, long sleeves, and a mini-length hem. Complete look with knee-high boots!Â
Fit & Features
- Ribbed knit fabric with knit lining, plenty of stretch
- Square neckline
- Long fitted sleeves
- A-line silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-5899
Category Name: Work Dresses & Outfits
Price: $38.90
Availability: In Stock
Available Color: IVORY
Available Size: XS, S, M, L
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Raise The Bar Ribbed Knit High Slit Midi Dress
Raise the bar in this knit high slit midi dress boasting a sultry off-the-shoulder neckline and a form-hugging fit. Pair with boots.
Fit & Features
- Ribbed knit fabric, plenty of stretch
- Off-the-shoulder neckline
- Fold over accent at bust
- High side slit
- Midi-length hem
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06005-2081
Category Name: Work Dresses & Outfits
Price: $7.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Cute Flirt Drop Waist Ruffled Hem Mini Dress
Show off your stunning figure in this smooth knit mini dress featuring a boat neckline, long fitted sleeves, a cute scoop back, a drop waist design, and a short tiered ruffled hem with an A-line fit for that flirty flair. Style with strappy mules!
Fit & Features
- Smooth nylon knit fabric, plenty of stretch
- Boat neckline
- Long fitted sleeves
- Scoop back
- Drop waist
- Tiered ruffled mini-length hem, A-line fit
- Runs true to size
Style Number/Barcode: 05102-5938
Category Name: Work Dresses & Outfits
Price: $9.97 $39.90
On Sale: Yes
Availability: In Stock
Available Color: BLACK
Available Size: S, M, L
Product Badge:- Sale
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Bold Allure Abstract Print Mesh Midi Dress
Show up and stun in this airy mesh midi dress accented with a trendy abstract print for a bold allure. The dress features a crew neckline, short cap sleeves, and a form-hugging silhouette to highlight your curves.
Fit & Features
- Abstract printed sheer mesh fabric with partial knit lining, plenty of stretch
- Lettuce edge hems
- Crew neckline
- Short cap sleeves
- Midi-length hem
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 05102-5628
Category Name: Work Dresses & Outfits
Price: $36.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M
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Sharp And Stylish Woven Belted Blazer Dress
Look sharp and stylish in this woven blazer dress. With its sheer peasant long sleeves, lapel collar neckline, and form-hugging silhouette, you'll be looking cute and refined. The double-breasted button closure and belted waist provide a tailored fit for a chic finish. Complete the look in sleek block heels for a lunch meet or a dressy bridal shower!
Fit & Features
- Sheer peasant long sleeves
- Lapel collar neckline
- Double-breasted button closures
- Belted waist
- Form-hugging, mini-length hem
- Woven fabric, sewn-in lining, no stretch
- Runs true to size
Style Number/Barcode: 06204-1720
Category Name: Work Dresses & Outfits
Price: $6.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Radiant Vacay V-Neck Floral Chiffon Skater Dress
Twirl your problems away on vacay in this radiant floral chiffon skater dress! The sheer peasant long sleeves, V-neckline, and corset-inspired bodice add a touch of romance, while the skater silhouette and ruffled hem bring a playful charm. Perfect for any occasion, from vacation to brunch! Complete the look in cute wedge sandals and sunnies.
Fit & Features
- Floral print, chiffon fabric lined with woven fabric
- Keyhole back with button closure
- Skater silhouette
- Ruffled short-length hem
- Sticky bra or pasties recommended
- Runs true to size
Style Number/Barcode: 05101-3186
Category Name: Work Dresses & Outfits
Price: $6.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Stripes In Style Off The Shoulder Mini Dress
Stay stylish in this trendy off-the-shoulder mini dress showcasing a classic striped pattern and a form-hugging fit. Pair with knee-high boots.
Fit & Features
- Ribbed knit fabrication
- Off-the-shoulder neckline
- Long dolman sleeves
- Stripes
- Mini length hem
- Runs true to size
Style Number/Barcode: 05102-5885
Category Name: Work Dresses & Outfits
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale