City Dresses
Step into the urban jungle and strut your stuff with our collection of city dresses that are as vibrant and dynamic as you are. Whether you're taking on a power lunch or dancing the night away, these dresses are your ticket to turning sidewalks into runways. From sleek silhouettes to playful patterns, our city dresses are here to make sure every street corner is your personal spotlight. So go ahead, let your style roam free and embrace the city life with confidence and flair.
$36.90
A denim satin mini dress with a ruched wrap silhouette and sleeveless square neckline.
$32.90
A lime yellow mesh mini dress with a cowl neckline and adjustable spaghetti straps for a chic night.
$32.90
A sage satin mini dress with an off-the-shoulder neckline and flattering A-line silhouette.
$36.90
A chic pink skater dress with a ribbed knit, off-the-shoulder neckline, and long fitted sleeves.
$40.90
A black glitter mini dress with a halter cowl neckline and side ruched seams.
$46.90
A black glitter crepe knit mini dress with sheer bell sleeves and a bodycon silhouette.
$46.90
A sleek black bodycon midi dress with a square neckline and stretchy double-lined knit fabric.
$36.90
A lavender ribbed knit mini dress with a scoop neckline and flattering skater silhouette.
$54.90
A navy blue floral satin dress with a lace-up back and flirty A-line silhouette.
$42.90
A black mesh mini dress with a plunging V-neckline and ruched details for a bold look.
$32.90
A chic red sleeveless midi dress with ruched seams and a curve-hugging bodycon silhouette.
$49.90
A lavender glitter skater dress with sheer peasant sleeves and a fit and flare silhouette.
$32.90
A green knit mini dress with a twist-front design and sultry keyhole waist cutout.
$42.90
A black ponte mini dress with sheer chiffon sleeves and a playful square neckline.
$9.97 $39.90 75% off
A black mini dress with a cutout bust, ruched wrap design, and sheer mesh long sleeves.
$32.90
A black bodycon mini dress with ruched mesh bell sleeves and a sweetheart neckline.
$9.97 $42.90 77% off
A slate A-line mini dress with a V-neckline and ruffled hem in soft knit fabric.
$44.90
A green off-the-shoulder glitter mini dress featuring a bodycon silhouette and sheer mesh fabric.
$19.97 $39.90 50% off
A khaki woven midi dress with a smocked bodice, ruffled hem, and dual spaghetti straps.
$36.90
A black glitter knit mini dress with an off-the-shoulder neckline and flirty A-line silhouette.
$32.90
A slinky black knit mini dress with a square neckline and flirty A-line silhouette.
$9.97 $38.90 74% off
A brown knit bodycon midi dress with flare cuff sleeves and a stylish V-neckline.
$46.90
An olive green gauze skater dress featuring V-neck cutouts, flowy sleeves, and a breezy silhouette.
$25 $34.90 28% off
A burgundy crepe mini dress with a faux corset bodice and flattering bodycon fit.
$42.90
A black ribbed knit bodycon mini dress with trendy cutouts and lattice accents for a chic look.
$65.90
A strapless floral skater dress featuring a bustier bodice, sweetheart neckline, and hidden side pockets.
$39.90
A strapless black and white striped mini dress with a cutout bodice and bodycon silhouette.
$59.90
A black sequin skater dress with an open back and tie-back bow, perfect for parties.
$21 $29.90 30% off
A charcoal plaid mini dress with sheer lace trims and a chic bow detail for date night.
$42.90
A red gingham skater dress with lace trim V-neckline and flattering drop waist seam.
$64.90
An elegant black mermaid dress with an off-the-shoulder neckline and ruched bodice.
$29.90
A taupe ribbed knit bodycon mini dress with spaghetti straps and a scoop neckline for casual outings.
$25 $34.90 28% off
A grey plaid strapless mini dress with a pleated hem and form-hugging knit fabric.
$39.90
A vibrant multi-color mesh mini dress featuring a cowl halter neckline, open back, and bodycon fit.
$39.90
A multicolor striped knit mini dress featuring bell sleeves, side cutouts, and a plunging neckline.
$42.90
A brown strapless mini dress with a bodycon silhouette, cargo pockets, and cotton-blend fabric.
$56.90
An ivory floral skater mini dress with a sweetheart neckline and adjustable spaghetti straps.
$34.90
A sleek green knit midi dress with a ruched V-neckline and high front slit.
$39.90
A teal glitter knit mini dress with a lace-up open back and asymmetrical hem.
$34.90
A yellow striped knit mini dress featuring a twisted strapless neckline and flattering bodycon silhouette.
$42.90
A black skater dress with a sweetheart neckline, spaghetti straps, and a low-cut back.
$79.90
A playful yellow A-line dress featuring side pleats, scuba woven fabric, and a flattering square neckline.
$52.90
A white mini bodycon dress with faux pearl embellishments and adjustable spaghetti straps.
$69.90
A white bodycon mini dress with iridescent rhinestones and faux pearls on sheer mesh fabric.
$19.97 $54.90 64% off
A wine-colored glitter-knit mini dress with a cowl neckline and ruched bodycon silhouette.
$42.90
A sultry wine mesh mini dress with a sweetheart neckline and alluring lace-up back.
$37.90
A pink satin strapless mini dress featuring a pleated bust and bodycon silhouette for parties.
$68.90
A mauve floral jacquard satin skater dress featuring a corset bodice and lace-up back design.
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The Marissa long satin dress brings elegance and sultriness to your formal night. The floor-length gown enhances your curves with a fitted bodice and flattering A-line silhouette while the high front slit provides movement. Fit & FeaturesStretch-satin fabric, non-see-through, double-lined bust, Sleeveless pleated cowl neckline, spaghetti straps, Slim-fit bodice, empire waistline, High front slit, floor-length hem, A-line silhouette, Runs true to size, Where to Wear:Prom, weddings, black-tie soirees, special date nights, and engagement parties. Free Shipping on All Orders Over $75. | Windsor Marissa Formal Satin Cowl Neck Dress in Green | Size: S | Satin Fabric
Shine bright and sparkle up the night in the gorgeous Leila mini dress. The dress boasts an alluring open back with a lace-up strappy design for a customized fit, and a short, curve-hugging silhouette. Shop Long Version: Kailani Formal Sequin Slit Mermaid DressFit & FeaturesSheer mesh fabric, full knit lining, moderate stretch, Sequin embroidery, scroll pattern, Sleeveless square neckline, adjustable spaghetti straps, Open back, lace-up strappy design, tie closure, High waist seam, lower back zipper, hook and eye closure, Mini-length hem, fitted bodycon silhouette, Runs true to size, Where to Wear:Prom, bachelorettes, birthdays, Vegas weekends, date nights Free Shipping on All Orders Over $75. | Windsor Leila Sequin Bodycon Mini Dress in Royal Blue | Size: XL | Knit Fabric/Mesh Fabric/Sheer Mesh Fabric
Look and feel like a sultry senorita in this mesh mini dress perfect for an chic night on the town! It features a sleeveless cowl neckline, dual adjustable spaghetti straps with a tie-neck closure, and side and back ruched seams designed to flaunt your curves along the bodycon silhouette. Complete the look with hoop earrings. Fit & FeaturesSleeveless cowl neckline, Dual adjustable spaghetti straps, tie-neck closure, Side and back ruched seams, Back zipper and hook-eye closure, Bodycon silhouette, mini-length hem, Mesh fabric, brushed soft knit stretchy lining, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Senorita Mesh Strappy Mini Dress in Red | Size: M | Knit Fabric/Mesh Fabric/Mesh Fabric
Every occasion is worth celebrating in this off-the-shoulder midi dress! The smooth and stretchy knit fabric includes a full-length knit lining for additional coverage. The off-the-shoulder neckline and short-sleeve cuffs add a touch of elegance, while the bodycon silhouette and flared midi-length hem accentuate your curves in all the right places. Complete the look with teardrop earrings and heels. Fit & FeaturesSmooth stretchy knit fabric with knit lining, Off-the-shoulder neckline, Short-sleeve cuffs, Bodycon fit, Flare hem, Style runs small, Free Shipping on All Orders Over $75. | Windsor Exceptional Off-The-Shoulder Flared Midi Dress in Natural | Size: XS | Knit Fabric
Bring on the cute attitude in this ponte mini skort brings featuring a flattering high-rise waist, and a skirt overlay designed with dual front slits along the form-hugging fit. Fit & FeaturesSmooth ponte knit fabric, minimal stretch, High-rise waist, Skirt overlay, dual front slits, Form-hugging silhouette, Mini-length hem, Shorts lining, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Cute Attitude Ponte Slit Mini Skort in Black | Size: XL | Knit Fabric
Show up and stun this formal season in the gorgeous Brynlee bodycon mini dress! She features a sleeveless square neckline, a built-in padded bust, halter spaghetti straps, an open back with a lace-up design for a customized fit, and a short, curve-hugging silhouette. The lined mesh fabric features all-over sequin embroidery in an intricate scroll pattern. Style the formal mini dress with clear heels for a night to remember. Fit & FeaturesSleeveless, square neckline, Built-in padded bust, no bra required, Halter spaghetti straps, back button closure, Open back, lace-up design, zipper closure, Bodycon silhouette, mini-length hem, Sequin scroll embroidery, mesh fabric, knit lining, minimal stretch, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Brynlee Sequin Embroidered Bodycon Dress in Sage | Size: S | Knit Fabric/Mesh Fabric/Mesh Fabric
A mini dress that brings the luxe sensation! The Keira faux pearl short dress is a stunning style with a strappy tie-back design and a bodycon silhouette that highlights your figure. Fit & FeaturesLightweight mesh fabric, stretchy knit lining, Faux pearl and bead embellishments, Sleeveless cowl neckline, Spaghetti straps, strappy tie-back design, open-back, Bodycon silhouette, mini-length hem, Runs true to size, Where to Wear:Prom, birthday parties, bachelorettes, Vegas weekends, rooftop cocktails Free Shipping on All Orders Over $75. | Windsor Keira Faux Pearl Strappy Open-Back Mini Dress in Light Blue-2 | Size: XS | Knit Fabric/Mesh Fabric/Mesh Fabric
A fashionista like you will adore this basic mini skirt for creating your day and night looks! Featuring an elasticized high-rise waistband, bodycon silhouette, and a flirty front hem slit on stretchy and smooth knit fabric. Style with a corset top and heels. Fit & FeaturesHigh-rise elasticized waistband, Bodycon silhouette, Front hem slit, Mini-length hem, Stretchy and smooth knit fabric, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Get Down With Basic Slit Mini Skirt in Black | Size: XL | Knit Fabric
Everyone will see you shining at the club in this glitter mini dress! It features an off-the-shoulder sweetheart neckline, sheer fitted ruched long sleeves, adjustable spaghetti straps, a ruched seam along the padded bust, a sheer bodice with trim, and side ruched seams that hug your curves on the bodycon silhouette. Complete the look with a clutch and heels. Fit & FeaturesOff-the-shoulder sweetheart neckline, Adjustable spaghetti straps, Sheer fitted ruched long sleeves, Ruched and padded bust, sheer bodice, trim, Side ruched seams, bodycon silhouette, mini-length hem, Glitter mesh fabric, sewn-in knit lining, moderate stretch, Runs true to size, Free Shipping on All Orders Over $75. | Windsor See Me Shining Glitter Off-The-Shoulder Mini Dress in Wine | Size: S | Knit Fabric/Mesh Fabric/Mesh Fabric
Both sexy and demure, the Kristen party dress wows from every angle! Perfect for bachelorette weekends, themed soirees, and formal birthdays! She features a sleeveless sweetheart neckline with a padded bust, cowl draping, adjustable spaghetti straps, and side ruched seams that hug your curves along her short bodycon silhouette. The formal party dress is composed of a faux pearl embellished mesh fabric with a stretchy knit lining. Complete the look in statement block heels. Fit & FeaturesSleeveless sweetheart neckline, Padded bust, cowl draping, Adjustable spaghetti straps, Side ruched seams, bodycon silhouette, Mini-length hem, Faux pearl embellishments, mesh fabric, stretch knit lining, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Kristen Faux Pearl Mini Party Dress in White | Size: XS | Knit Fabric/Mesh Fabric/Mesh Fabric
City Dresses
You know that feeling when the city lights start flickering on, the skyline glows, and suddenly every sidewalk feels like your personal runway? That’s exactly the energy city dresses bring—ready for anything, made for everywhere. Whether you’re dashing from a rooftop brunch with the girls to a gallery opening or just want to turn the farmer’s market into your own little fashion show, the right city dress is your secret weapon. These aren’t just dresses; they’re confidence boosters, crafted to keep up with your wildest plans and spontaneous adventures. Think breezy fabrics that catch the breeze as you hail a cab, sleek silhouettes that slip seamlessly from day to night, and little details—like a flirty cutout or a bold print—that spark compliments from strangers and friends alike. City dresses are all about versatility and attitude. They’re for the girl who wants to look pulled together with zero fuss, the one who’s always got a backup plan for her backup plan, and the friend who knows how to make every moment feel like a main character moment.
Shopping for the perfect city dress is all about finding those pieces that feel like they just *get* you. Maybe you love a classic shirt dress that looks impossibly chic with sneakers or ankle boots, or perhaps you’re vibing with a fitted midi that hugs in all the right places and says, “Yes, I woke up like this.” For our Windsor girls who are gifting, city dresses are the ultimate “just because” treat for your bestie, your sister, or even your mom—especially if you’re on the hunt for casual dresses for women over 50 that don’t compromise on style or comfort. City dresses make amazing gifts because they’re practical yet exciting, and let’s be real, who doesn’t love unwrapping something that instantly makes them feel like a million bucks? If you’re building your own collection, consider how a dress city vibe can work for everything from coffee runs to date nights. Look for pieces that play well with your favorite jackets, bags, and statement shoes. And don’t sleep on those windsor dresses that bring a little extra drama—think ruching, high slits, or daring necklines—because sometimes you just need to remind everyone you’re the one setting the bar.
When it comes to making your city dress work for you, it’s all about the styling game. Toss on an oversized blazer for an office-ready twist, layer up with chunky jewelry for a night out, or keep it low-key with a denim jacket and some killer sunglasses for a chill day vibe. City dresses are the definition of low-maintenance glam, perfect for the girl who wants to look like she tried (even if she rolled out of bed 20 minutes ago). No matter your age, style, or plans, there’s a city dress that’ll match your energy and keep you feeling unstoppable from sunrise to last call. Ready to find your next obsession? Check out our Shopping Dresses page for the latest drops and endless inspo. Because every city adventure deserves a dress that’s just as bold as you are.