Workwear Dresses

Workwear dresses are your secret weapon for turning every office hallway into your personal runway. Whether you're going from boardroom boss to post-meeting happy hour hero, these looks are made to keep up with your hustle (and your style). From power moves to coffee breaks, you’ll be serving confidence and main character energy all day long. Get ready to break the glass ceiling—and a few hearts—while you’re at it.

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$36.90

4.714286 star rating

A dark denim ribbed knit skater dress with an off-the-shoulder folded neckline and long sleeves.

$46.90

4.666667 star rating

A black knit midi sweater dress with abstract stripes, square neckline, and back slit accent.

$46.90

4.888889 star rating

A brown woven midi dress with a ditsy floral pattern, corset bodice, and high front slit.

$28.90

5 star rating

A chic ivory cable knit midi dress featuring a strapless neckline and form-hugging silhouette.

$46.90

A taupe plaid strapless skater dress with a sweetheart neckline and pleated mini silhouette.

$29.90

5 star rating

An olive green cable knit midi dress featuring a mock neck, sleeveless design, and side slit.

$49.90

5 star rating

A grey pinstripe mini dress in woven fabric featuring a strapless collared neckline and pleated hem.

$36.90

4.142857 star rating

A black knit midi dress with a sleeveless square neckline, ruching, and pleated mermaid silhouette.

$39.90

5 star rating

A sleeveless ivory ribbed knit midi dress featuring a mock neckline and flattering bodycon silhouette.

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Perfectly Stylish Sleeveless Ribbed Knit Midi Dress in Black
(46) 4.5869565 star rating

Achieve a perfectly stylish everyday look with this sleeveless ribbed knit midi dress! Designed with a comfortable ribbed knit fabric offering plenty of stretch, it features a V-neckline, spaghetti straps, a midi-length hem with a chic high front slit, and a form-hugging silhouette. Pair with a cropped denim jacket and clear mules. Fit & FeaturesStretchy ribbed knit fabric, V-neckline, Spaghetti straps, High front slit, Form-hugging fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Perfectly Stylish Sleeveless Ribbed Knit Midi Dress in Black | Size: M | Knit Fabric

Windsor Chic Fall Vibe Ditsy Floral Corset Midi Dress in Brown
(27) 4.888889 star rating

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 & FeaturesDitsy 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, Free Shipping on All Orders Over $75. | Windsor Chic Fall Vibe Ditsy Floral Corset Midi Dress in Brown | Size: S | Woven Fabric

Windsor Smooth Talker Strapless Bodycon Midi Dress in Mocha
(11) 4.909091 star rating

Show off your smooth moves in this strapless bodycon midi dress perfect for dressing up or down for any occasion! Fit & FeaturesRib knit fabric, sewn-in knit lining, moderate stretch, Strapless neckline, Side slit, Bodycon silhouette, Midi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Smooth Talker Strapless Bodycon Midi Dress in Mocha | Size: XS | Knit Fabric

Windsor Dinner Downtown Sleeveless Ruched Midi Dress in Brown
(10) 5 star rating

The perfect chic sleeveless midi dress for grabbing dinner downtown! Crafted from smooth knit fabric, this crew neck dress boasts curve-accentuating ruched seams along the bodycon silhouette and a sleek midi-length hem. Pair with kitten heels and a clutch. Fit & FeaturesSmooth knit fabric, stretchy knit lining, Sleeveless crew neck, Side ruched seams, Bodycon silhouette, Midi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Dinner Downtown Sleeveless Ruched Midi Dress in Brown | Size: XS | Knit Fabric

Windsor Blissful Cutie Halter Cutout Skater Dress in Blue
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(7) 5 star rating

Get swept off your feet in this cute skater dress for any casual occasion! With its halter neckline and cutout bodice, this dress is designed to show off your figure, while the ruffled mini-length hem adds a flirty touch. Fit & FeaturesGauze woven fabric, woven lining, Halter neckline with spaghetti strap ties, Stretchy smocked bust, Cutout bodice, Ruffled skater silhouette, Mini-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Blissful Cutie Halter Cutout Skater Dress in Blue | Size: L | Gauze/Woven Fabric

Pretty Vibes Eyelet Knit Layered Skater Dress in White-2
(5) 4.6 star rating

Show off pretty vibes in this adorable layered skater dress made with breezy eyelet knit fabric. Pair with sneakers for a cute casual look or wedges for a dressier style. Fit & FeaturesStretchy sheer eyelet knit fabric, partial knit lining, Square neckline, Spaghetti straps, Double-layered skater skirt, Short fit-and-flare silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Pretty Vibes Eyelet Knit Layered Skater Dress in White-2 | Size: L | Knit Fabric

Windsor Sway With Me Halter V-Neck Paisley Skater Dress in Navy Blue
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(4) 5 star rating

This breezy skater dress brings the romance with a halter neckline and swingy silhouette made to float with you. Perfect for golden hour snaps, weekend wandering, or spontaneous getaways! Fit & FeaturesPaisley print, woven fabric, bust lining, Halter V-neckline with spaghetti strap ties, Stretchy smocked bust, Tie back design, Skater silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sway With Me Halter V-Neck Paisley Skater Dress in Navy Blue | Size: L | Woven Fabric

Windsor Chic Paradise Halter Open Back Slit Midi Dress in Red Brown
(4) 5 star rating

Own the spotlight on vacation in this midi dress! Featuring a bold halter neckline and an sexy open back, this dress exudes allure, while the bodycon silhouette and slit add a flattering look. Fit & FeaturesSlinky knit fabric, smooth stretchy knit lining, Halter cowl neckline, beaded spaghetti strap tie, Open back with spaghetti strap tie, Bodycon silhouette, Slit accent, midi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Chic Paradise Halter Open Back Slit Midi Dress in Red Brown | Size: L | Knit Fabric

Casually Sultry Strapless Bodycon Midi Dress in Red Brown
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(4) 4.75 star rating

Strut looking casually sultry in this strapless midi dress that accentuates your curves and can easily be dressed up or down! Fit & FeaturesBrushed knit double-lined stretchy knit fabric, Strapless neckline, Side ruched seams, Bodycon silhouette, Midi-length hem, side slit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Casually Sultry Strapless Bodycon Midi Dress in Red Brown | Size: L | Knit Fabric

Windsor It Girl High Neck Lace Up Maxi Dress in Black
(4) 4.75 star rating

That “did she just walk in?” kind of dress. The bodycon knit dress hugs in all the right places with a lace-up back that does the flirting for you. Fit & FeaturesTexture knit fabric, knit lining, High neckline, Spaghetti straps, Lace-up back, Bodycon fit, maxi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor It Girl High Neck Lace Up Maxi Dress in Black | Size: M | Knit Fabric

Workwear Dresses