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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Total Feels Sleeveless Maxi Sweater Dress
You'll love how you feel in this sleeveless maxi sweater dress perfect for casual day-to-night occasions! The maxi-length dress features a mock neckline, a form-hugging fit, and a flirty high slit along the hem. Complete the look in booties.
Fit & Features
- Sleeveless mock neck
- Form-hugging fit
- High slit
- Maxi-length hem
- Sweater ribbed knit fabric
- Moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1900
Category Name: Work Dresses & Outfits
Price: $3.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Floral Beauty Chiffon A-Line Midi Dress
Create a truly beautiful look for spring and summer weddings in this floral chiffon midi dress! The airy chiffon fabric showcases a blooming floral print and includes a stretchy knit lining for coverage. The tea-length dress is shaped with a sleeveless square neckline and adjustable spaghetti straps for a perfect customized fit. Smocking at the back provides added stretch and features a secure zipper closure. The fitted high waist seam flows out to a classic A-line silhouette with a front slit for extra movement. Style this pretty midi dress with sleek hoops and block heels.
Fit & Features
- Sheer chiffon fabric with stretchy knit lining, floral print
- Sleeveless square neckline, no-slip strip, adjustable spaghetti straps
- Stretchy smocked back, zipper with hook and eye closure
- High waist seam, front slit
- A-line silhouette
- Strapless or sticky bra recommended
- Runs true to size
Style Number/Barcode: 05101-2356
Category Name: Work Dresses & Outfits
Price: $21.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Off My Mind Cutout Long Sleeve Ribbed Knit Midi Dress
Make an unforgettable appearance in this long-sleeved midi dress at brunch or casual parties! The midi dress is designed with an off-the-shoulder neckline, a twisted bust with a sultry cutout, and a bodycon fit on stretchy ribbed knit fabric. Complete the look in strappy heels.
Fit & Features
- Ribbed knit fabric with moderate stretch
- Off-the-shoulder neckline
- Fitted long sleeves
- Twisted bust, cutout
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5280
Category Name: Work Dresses & Outfits
Price: $19.97 $35.90
On Sale: Yes
Availability: Out of Stock
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Find Your Style Button Down Pleated Mini Dress
Make a style statement in this woven shirt mini dress! Featuring long sleeves with button cuffs, a collar neckline, a button down front, and a flattering A-line silhouette and pleated mini-length hem for an adorable and undeniable stylish look. Complete the look in knee-high boots for brunch downtown!
Fit & Features
- Long sleeves with button cuffs
- Collar neckline
- Button down front
- A-line silhouette
- Pleated mini-length hem
- Woven poplin fabric, no stretch
- Runs true to size
Style Number/Barcode: 05102-5379
Category Name: Work Dresses & Outfits
Price: $14.97 $39.90
On Sale: Yes
Availability: Out of Stock
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Showstoppin' Staple Long Sleeve Maxi Dress
Put your curves on display in this basic maxi dress perfect for dressing up or down! The long dress features fitted long sleeves, a classic crew neck, and a flattering bodycon silhouette on hacci rib knit fabric. Complete the look with strappy heels and a purse!
Fit & Features
- Hacci rib knit fabric, plenty of stretch
- Fitted long sleeves
- Crew neckline
- Bodycon silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-5331
Category Name: Work Dresses & Outfits
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Glimmer Girl Long Sleeve Mini Sweater Dress
It's the season of glam, and you'll shimmer and glimmer in this mini sweater dress! It features a sweetheart neckline, long fitted sleeves, a mini-length hem with a fab side slit, and a bodycon silhouette to show off your curves. The ribbed knit fabric features a sparkly lurex threaded design for a glam touch. Style this sweater dress with strappy mules for a holiday party!
Fit & Features
- Sweetheart neckline
- Long fitted sleeves
- Mini-length hem, side slit
- Bodycon silhouette
- Ribbed knit fabric, lurex threaded design
- Plenty of stretch
- Runs true to size
Style Number/Barcode: 06005-1771
Category Name: Work Dresses & Outfits
Price: $3.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Abstract Beauty Printed Slit Midi Dress
Embrace your inner beauty in this abstract printed slit midi dress for any casual occasion! Featuring a flattering sleeveless square neckline perfect for layering, delicate spaghetti straps, and a bodycon fit, this dress flatters every figure. The front slit and midi-length hem add a touch of elegance, while the abstract print and mesh fabric create a unique style. Complete the look in mules and a cropped jacket.
Fit & Features
- Abstract print, stretchy mesh fabric, sewn-in knit lining
- Spaghetti straps
- Bodycon fit
- Front slit
- Runs true to size
Style Number/Barcode: 05102-5736
Category Name: Work Dresses & Outfits
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Strut And Snap Ribbed Knit Midi Dress
Strut it out in a knit midi dress that is perf for every day! Designed with a ribbed knit fabric, this dress offers a form-hugging fit with a moderate stretch. It features a sleeveless square neckline, tank shoulder straps, a high side slit accented with glossy metal buttons, and a midi-length hem. Complete the look with mules.
Shop More Sweater Dresses: Sweater Dress Collection
Fit & Features
- Ribbed knit fabric with moderate stretch
- Square neckline
- Tank shoulder straps
- Metal button accents
- Side slit
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06005-1167
Category Name: Work Dresses & Outfits
Price: $39.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
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Make It Work Sleeveless Tank Midi Dress
Make a bold statement in any setting in this sleeveless midi dress perfect for work or play! The midi dress features a sleeveless square neckline, an underbust seam, tank shoulder straps, a bodycon silhouette that flaunts your curves, and a flirty center back slit accent on smooth woven fabric. Complete the look with pumps and a posh jacket for business mixers and happy hour!
Fit & Features
- Sleeveless square neckline
- Tank shoulder straps
- Underbust seam
- Bodycon silhouetteÂ
- Midi-length hem, center back slit
- Smooth woven fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 05101-2871
Category Name: Work Dresses & Outfits
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Adorable Factor Chiffon Sweetheart Midi Dress
Raise the bar looking adorable in this chiffon midi dress perfect for upcoming dressy occasions! The midi-length dress features short puff sleeves, a sweetheart neckline, a ruched bust, and a flirty cutout waist to show some skin. The flattering A-line silhouette boasts a playful front slit and a flowy midi hem. Complete the look with cute sandals and jewelry!
Fit & Features
- Short puff sleeves
- Sweetheart neckline, stretchy smocked back
- Ruched bust, cutout waist
- A-line silhouette, front slit
- Midi-length hem
- Chiffon woven fabric, no stretch
- Runs true to size
Style Number/Barcode: 05101-3189
Category Name: Work Dresses & Outfits
Price: $10.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Casual And Cozy Off-The-Shoulder Sweater Dress
This on-trend sweater dress is the casual and cozy staple you need this fall and winter season. It features a chic off-the-shoulder neckline, long sleeves, a short-length hem, and a relaxed fit. The ribbed sweater knit fabric offers a moderate stretch. Pair this sweater dress with over-the-knee boots for a stylish and elevated look.
Fit & Features
- Off-the-shoulder neckline
- Long sleeves
- Short-length hem
- Relaxed silhouette
- Ribbed sweater knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1764
Category Name: Work Dresses & Outfits
Price: $15.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Major Charm Crepe One Shoulder Dress
Bring major charm in this one-shoulder midi dress showcasing a sleek and sultry silhouette perfect for flaunting curves! It features a sleeveless bodice with a single spaghetti strap, a tie-front waist belt, and a front-side slit accent on crepe fabric. Complete the look in simple nubuck block heels.
Fit & Features
- Sleeveless one-shoulder neckline
- Single spaghetti strap
- TIe-front waist belt
- Bodycon silhouette
- Front side slit. midi-length hem
- Crepe fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05101-1699
Category Name: Work Dresses & Outfits
Price: $19.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Stroll Along Surplice Tie Waist Mini Dress
Stroll along the city streets in this casual mini dress perfect for a day out! The mini dress features relaxed long sleeves with banded cuffs, a V-neckline with a surplice accent, a tie-waist belt, and a flattering bodycon fit on stretchy knit fabric. Complete the look with a crossbody bag.
Fit & Features
- Relaxed long sleeves, banded cuffs
- V-neckline, surplice accent
- Tie-waist belt
- Bodycon fit
- Mini-length hem
- Stretchy knit fabric
- Runs true to size
Style Number/Barcode: 05102-5354
Category Name: Work Dresses & Outfits
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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It's A Must Collared Denim Mini Dress
This denim mini dress is a must for curating a cute and trendy lineup this season! The short dress features long sleeves, a collar neckline, zipper front closure, dual flap pockets with snap-button closures and lower pockets, an elasticized waist with belt loop accents, a bodycon fit, and a mini-length hem. Complete the look in pointed-toe booties for a day out with friends!
Fit & Features
- Long sleeves, collar neckline
- Zipper front closure
- Flap pockets with snap-button closures
- Lower pockets
- Bodycon fit, mini-length hem
- Rigid denim fabric, no stretch
- Runs true to size
Style Number/Barcode: 05102-5364
Category Name: Work Dresses & Outfits
Price: $54.90
Availability: Out of Stock
Product Badge:- Sale
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Make A Debut Plaid Strapless Pleated Mini Dress
Make a debut in classic plaid and on-trend silhouette! This plaid mini dress is sure to stand out from any crowd. Featuring a strapless neckline, form-hugging bodice, belt loop accents, and a flirty pleated mini-length hem. Complete the look in lug boots for an edgy vibe!
Fit & Features
- Strapless neckline
- Back zipper closure
- Form-hugging bodice
- Belt loop accents
- Pleated mini-length hem
- Plaid print, woven fabric, knit lining at the bust, minimal stretch
- Runs true to size
Style Number/Barcode: 05102-5415
Category Name: Work Dresses & Outfits
Price: $19.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Effortlessly Trendy Striped Slit Maxi Dress
A trendy maxi dress features a flattering square neckline, form-hugging fit, and a high front slit to show off your shoes. Perfect for styling with a denim jacket and sandals.
Fit & Features
- Striped pattern, stretchy knit fabric
- Square neckline, spaghetti straps
- High front slit
- Form-hugging maxi-length fit
- Runs true to size
Style Number/Barcode: 05102-5867
Category Name: Work Dresses & Outfits
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Make An Appearance Lace-Up Sweater Mini Dress
Make an appearance in this sweater mini dress for dates to dinners! The mini dress features fitted long sleeves with flared cuffs and eye-catching lace-up packets, a mock neckline, and a flattering bodycon silhouette, on rib knit sweater fabric. Complete the look with simple hoop earrings and heels.
Fit & Features
- Fitted long sleeves
- Flared cuffs, lace-up plackets
- Mock neckline
- Bodycon silhouette
- Mini-length hem
- Rib-knit sweater fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1741
Category Name: Work Dresses & Outfits
Price: $3.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Babe With Taste Buckle Strap Pleated Mini Dress
Let everyone know you're a babe with taste in this pleated mini dress! Made from a twill woven fabric for structure and has a stretchy knit lining for coverage. With a square neckline and seam detailing, this dress exudes style. The adjustable buckle shoulder straps provide a customizable fit, while the fitted bodice and pleated mini-length hem flatter your figure. Complete the look with sunglasses and a purse!
Fit & Features
- Twill woven fabric, stretchy knit lining
- Square neckline
- Back zipper closure
- Adjustable buckle shoulder straps
- Pleated mini-length hem
- Runs true to size
Style Number/Barcode: 05102-5629
Category Name: Work Dresses & Outfits
Price: $6.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Impress Me Pinstripe Strapless Mini Dress
This pinstripe mini dress is sure to impress! Featuring a strapless foldover neckline with non-slip grip lining, a stretchy smocked back, form-hugging silhouette, and a flirty front slit along the hem. Complete the look in a cropped blazer for a posh vibe!
Fit & Features
- Strapless foldover neckline
- Non-slip grip lining
- Stretchy smocked back
- Form-hugging silhouette, front slit, mini-length hem
- Back zipper and hook-eye closure
- Pinstripe print, woven fabric, and lining
- Runs true to size
Style Number/Barcode: 05102-5469
Category Name: Work Dresses & Outfits
Price: $19.97 $36.90
On Sale: Yes
Availability: Out of Stock
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Your Needs Met Sleeveless Slit Midi Dress
A sleeveless midi dress that meets all of your style needs! This knee-length dress features a square neckline, wide shoulder straps, a flattering bodycon silhouette, and a front slit on woven fabric. Style this midi dress with sleek stiletto heels for a cocktail party or rehearsal dinner!
Fit & Features
- Sleeveless square neckline
- Wide shoulder straps
- Back zipper closure
- Bodycon silhouette, front slit
- Midi-length hem
- Woven fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 05101-2884
Category Name: Work Dresses & Outfits
Price: $5.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Garden Chic Floral Chiffon Midi Dress
Enchanting and chic, this floral chiffon midi dress is perfect for a garden wedding. It features a sleeveless sweetheart neckline with a bust outline, adjustable spaghetti straps, a high waist seam, a smocked back panel with a zipper closure, a midi-length hem with a high front slit, and a flowy A-line silhouette. The airy chiffon fabric features a romantic blooming floral print alongside a dainty flower pattern. Style with clear block heels.
Fit & Features
- Sleeveless sweetheart neckline, padded bust and outline
- Adjustable spaghetti straps
- High waist seam, stretchy smocked back, zipper and hook-eye closure
- Midi-length hem
- Front slit, A-line silhouette
- Floral print, chiffon fabric, smooth stretchy knit lining
- Style runs small
Style Number/Barcode: 05101-2212
Category Name: Work Dresses & Outfits
Price: $20.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Jullian Formal Crepe Off-The-Shoulder Midi Dress
Special Occasion
A timeless addition to your wardrobe, the Jullian formal midi dress is beautiful and perfect for banquets or formal parties! With its foldover off-the-shoulder neckline, bodycon fit, and midi-length hem with a front slit - you'll exude classic sophistication. The formal midi dress is composed of a sleek crepe fabric with a bust knit lining and plenty of stretch for comfort! Complete the look with strappy block heels.
Fit & Features
- Foldover off-the-shoulder neckline
- Bodycon fit
- Front slit, midi-length hem
- Crepe fabric, bust knit lining
- Strapless bra recommended
- Runs true to size
Style Number/Barcode: 05001-2035
Category Name: Work Dresses & Outfits
Price: $24.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Preppy Spirit Collared Midi Dress
Get some pep in your step by styling this casual midi dress for art shows or family dinners! The mid-length dress features a collared V-neckline, long fitted sleeves, and a bodycon silhouette on stretchy ribbed knit fabric. Style with knee-high boots to complete the look!
Fit & Features
- Collared V-neckline
- Long fitted sleeves
- Bodycon silhouette
- Midi-length hem
- Ribbed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4785
Category Name: Work Dresses & Outfits
Price: $19.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Chic In The City Turtleneck Mini Dress
You'll look chic as you take a stroll in the city in this trendy turtleneck mini dress! It features a turtleneck that you can fold over, long fitted sleeves, ruching down the side seams, a mini-length hem, and a bodycon silhouette to showcase your curves. The soft brushed knit fabric offers plenty of stretch for comfortable wear. Style this mini dress with a faux leather blazer and over-the-knee boots for a cute fall 'fit.
Fit & Features
- Turtleneck
- Long fitted sleeves
- Ruched side seams
- Mini-length hem
- Bodycon silhouette
- Brushed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5220
Category Name: Work Dresses & Outfits
Price: $17.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale