Casual Date Night Outfits
Hey, girl! Ready to make some heads turn on your next casual date night? Whether it's a moonlit stroll or a cozy dinner for two, we've got the ultimate lineup of outfits that scream effortless chic. Think flirty skirts, dreamy dresses, and tops that bring all the charm without breaking a sweat. Your wardrobe's about to become your new partner in crime, ensuring you look fabulous while keeping it cool and laid-back. So go ahead, make that date unforgettable with outfits that are as stunning as they are comfortable. Casual date night outfits have never looked so good!
$32.90
A chic black strapless mini dress with pleated bust and flowy A-line silhouette in stretchy knit.
$32.90
A lime yellow mesh mini dress with a cowl neckline and adjustable spaghetti straps.
$34.90
A sleek pink satin-like tie-front blouse with a collared neckline and cropped hem.
$34.90 - $42.90
A chartreuse crepe halter jumpsuit featuring a plunging neckline, midriff cutout, and straight-leg silhouette.
$84.90
A strapless black bodycon mini dress with beaded mesh fabric and a cowl neckline.
$9.97 $22.90 56% off
A sleek black faux leather mini skirt with a high waist, front slit, and hidden back zipper.
$46.90
A black strapless romper with rhinestone embellishments and a form-hugging silhouette for standout style.
$46.90
A vibrant yellow skater dress with a ruffled skirt, halter tie-back, and smocked high waist.
$9.97 $64.90 85% off
A sage woven skater dress with a lace-up back and asymmetric drop-waist for a sweet summer look.
$39.90
A navy blue knit mini dress featuring a sleeveless V-neck, padded bust, and ruched bodycon silhouette.
$48.90
An elegant black off-the-shoulder midi dress with ruched sides and a flattering bodycon fit.
$46.90
A sleek black bodycon midi dress with a square neckline and stretchy double-lined knit fabric.
$42.90
A black mesh mini dress with a plunging V-neckline and ruched details for a bold look.
$49.90
A chic brown knit jumpsuit featuring an open back, hoop neckline, and wide-leg silhouette.
$32.90
A chic brown sleeveless midi dress in smooth knit fabric with flattering ruched seams and bodycon fit.
$35.90
A white knit bodycon midi dress featuring a square neckline, spaghetti straps, and side ruched seams.
$48.90
A white eyelet knit mini skater dress featuring a flirty tie-back and tiered ruffled hem.
$42.90
A strapless black lace skater dress featuring a ruffled mini hem and stretch knit lining.
$44.90
A white strapless mini dress featuring lace corset bodice, chiffon ruffled skater skirt, and sweetheart neckline.
$32.90
A sultry black knit halter top featuring a plunge lace trim neckline and flattering corset bodice.
$42.90
A black crepe mini dress featuring a crew neck, front pleating, and a flattering bodycon silhouette.
$9.97 $39.90 75% off
A black bodycon mini dress with an asymmetrical hem, cutout bust, and sheer mesh sleeves.
$9.97 $42.90 77% off
A chic black strapless midi dress with a cowl-draped neckline and asymmetric hem for allure.
$44.90
A black floral maxi dress featuring sheer mesh, a lace-up strappy back, and a form-hugging silhouette.
$26.90
A stylish black halter crop top with a knotted bust and smooth stretchy knit fabric.
$9.97 $33.90 71% off
A denim satin mini dress with a lace-up back, spaghetti straps, and padded bra cups.
$32.90
A green knit mini dress with a twist-front design and sultry waist cutout for night-outs.
$22.90
A sleek black bodycon mini skort with faux leather fabric and a high-rise waist.
$46.90
A sultry black jumpsuit featuring a cowl halter neckline, cutout back, and wide-leg silhouette.
$19.97 $34.90 43% off
A sleek pink knit mini dress featuring a ruched bust, off-the-shoulder neckline, and bodycon silhouette.
$32.90
A black mini bodycon dress with a sweetheart neckline and dramatic ruched bell sleeves.
$29.97 $59.90 50% off
A black lace bodycon mini dress featuring faux pearl embellishments and adjustable spaghetti straps.
$42.90
A denim blue knit bodycon midi dress featuring a cutout back, twist straps, and a side slit.
$39.90
A black stretchy mini dress featuring a halter plunge neckline, front cutout, and bodycon silhouette.
$44.90
A strapless white mini dress in pleated ponte knit fabric with a form-hugging bodycon silhouette.
$20.97 $46.90 55% off
An olive green gauze skater dress featuring V-neck cutouts, flowy sleeves, and a breezy silhouette.
$42.90
A strapless black knit mini dress featuring a form-hugging silhouette and playful ruffled hem.
$39.90
A multicolor striped knit mini dress featuring bell sleeves, side cutouts, and a plunging V-neckline.
$39.90
A sultry black romper featuring a plunge halter neckline and ruffled short hem in stretchy knit fabric.
$69.90
A burgundy satin mini dress with a corset bodice, applique design, and adjustable spaghetti straps.
$39.90
A denim mini skort with a mid-rise adjustable belted waist and form-hugging silhouette.
$44.90
A chic black mesh and satin short dress with sheer sleeves and an alluring back cutout.
$49.90
A brown mesh maxi dress featuring a bold floral print, drapey cowl halter neckline, and curve-hugging fit.
$35.90
A red sheen knit mini dress featuring a cutout bust, sweetheart neckline, and flattering A-line silhouette.
$34.90
A strapless red-brown knit midi dress featuring side ruching, a bodycon silhouette, and a side slit.
$21 $29.90 30% off
A charcoal plaid mini dress with sheer lace trims and a chic bow detail for date night.
$25 $34.90 28% off
A burgundy crepe mini dress with a faux corset bodice and flattering bodycon fit.
$42.90
A berry velvet mini dress featuring a bold flocked cheetah print and sleek one-shoulder bodycon silhouette.
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Slip into the luxe vibes of Mayra! Designed to highlight your figure, this formal satin dress delivers a chic form-hugging fit and a high slit for effortless movement. Fit & FeaturesSmooth satin-knit fabric, moderate stretch, Sleeveless square neckline, spaghetti straps, Fitted bodice, side hip pleating, Form-fitting silhouette, high-cut front slit, Floor-length hem, Style runs small, Where to Wear:Homecoming, weddings, black-tie parties, galas, military balls, engagement parties, rehearsal dinners, bridal celebrations, birthday events, milestone celebrations Free Shipping on All Orders Over $75. | Windsor Mayra Formal Satin Slit Long Dress in Sage | Size: S | Satin Fabric
Create a captivating entrance in this formal wrap dress for your next soiree. All eyes are on you in this stylishly chic long formal dress with a plunging V-neckline to perfectly display a sparkling rhinestone lariat or delicate layers of dainty necklaces. Fit & FeaturesCrepe fabric, moderate stretch, Asymmetrical wrap V-neckline, Adjustable spaghetti straps, Ruched detailing, slim-fit bodice, High front slit, floor-length wrap silhouette, Runs true to size, Where to Wear:Prom, black-tie weddings, and formal parties. Free Shipping on All Orders Over $75. | Windsor Sasha Formal High Slit Wrap Dress in Black | Size: XS | Rhinestone
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
Chic and glamorous, the Rowena sequin mermaid long dress will stylishly elevate your formal night-out look. With a lace-up strap design and fitted mermaid silhouette with a high slit, you'll deliver stunning style. Fit & FeaturesSheer mesh fabric, knit lining, moderate stretch, embroidered sequin scroll design, Sleeveless square neckline, padded bust, Spaghetti straps, open back, lace-up strap design, tie closure, Lower back zipper with hook and eye closure, High waist seam, Fitted floor-length mermaid silhouette, high front slit, Runs true to size, Where to Wear:Prom, black-tie parties and galas, fancy engagement parties Free Shipping on All Orders Over $75. | Windsor Rowena Sequin Mermaid Dress in Navy Blue | Size: M | Knit Fabric/Mesh Fabric/Sheer Mesh Fabric
Get all wrapped up in this stylish sleek satin mini dress. Dance the night away at that upcoming wedding or celebrate a girl's night in this statement dress that will have all eyes on you. The dress features a sleeveless square neckline, spaghetti straps, and a ruched wrap silhouette that hugs curves in all the right places. The mini-length dress is composed of a satin-like fabric that offers a moderate stretch. Complete your look with rhinestone earrings and strappy heels. Fit & FeaturesSleeveless square neckline, spaghetti straps, Strapless bra recommended, Ruched wrap-front detail , Mini-length bodycon silhouette , Satin-like fabric, sheen finish, Form-hugging fit, moderate stretch, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Wrapped In Stylish Satin Mini Dress in Denim | Size: XS | Rhinestone/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: L | Knit Fabric/Mesh Fabric/Sheer Mesh Fabric
Make a sparkly statement at your next soiree in the trendy glam Addison glitter formal dress! Bring radiance to the room in this floor-length dress with a sleek design that fits like a glove. Fit & FeaturesSheer glitter mesh fabric, full knit stretchy lining, Sleeveless cowl neckline, spaghetti straps, High waist seam, Floor-length fitted silhouette, Runs true to size, Where to Wear:Prom, black tie weddings, galas, special date nights, rehearsal dinner Free Shipping on All Orders Over $75. | Windsor Addison Glitter Mesh Formal Dress in Black | Size: XS | Knit Fabric/Mesh Fabric/Mesh Fabric
This adorable strapless A-line mini dress is so your vibe! Designed with a stretchy lined knit fabric, it features a strapless straight-across neckline, chic pleated detailing at the bust, and a flirty flowy A-line silhouette on the mini-length hem. Style for a girl's night with statement earrings and strappy mules. Fit & FeaturesStretchy knit fabric with knit lining, Strapless straight neckline, no-slip strip, Pleated bust, A-line fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor So Your Vibe Strapless A-line Mini Dress in Wine | Size: XS | Knit Fabric
Embellished with light-catching sequins, the Bethanie formal dress is a clear stunner with a lace-up back and a flattering mermaid silhouette with a floor-length hem. Fit & FeaturesSequin-scroll pattern, mesh fabric, stretch knit lining, Sleeveless V-neckline, padded bust, Lace-up back, zipper and hook-eye closure, Mermaid silhouette, Floor-length hem, Runs true to size, Where to Wear:Prom, black-tie events, formal weddings, and upscale parties. Free Shipping on All Orders Over $75. | Windsor Bethanie Formal Sequin V-Neck Mermaid Dress in Yellow | Size: S | Knit Fabric/Mesh Fabric/Mesh Fabric
Sultry and stunning, the Alisha formal dress will keep all eyes on you. With thin rhinestone detailed straps that give effortless sparkle and a curve-hugging silhouette, and an alluring high slit. Fit & FeaturesLightweight, breathable stretchy fabric, Sleeveless cowl neckline, Rhinestone detailed straps, High waist seam, Floor-length hem, form-fitting silhouette, high slit, Runs true to size, Where to Wear:Prom, glamorous evenings, dinner parties, weddings Free Shipping on All Orders Over $75. | Windsor Alisha Rhinestone Strap Formal Dress in Black | Size: L | Stretchy Fabric/Rhinestone
Casual Date Night Outfits
When it comes to nailing the casual date night vibe, it’s all about striking that sweet spot between effortless and unforgettable. Whether you’re heading to your favorite rooftop spot, grabbing coffee at the cutest café in town, or just catching a movie under the stars, your outfit should feel like you—comfortable, confident, and just a little bit daring. Think well-fitted denim that hugs in all the right places, paired with tops that make you want to twirl in front of the mirror just because. There’s something about slipping into a flirty top with subtle details—maybe a hint of lace, a playful cut-out, or a bold color—that just sets the tone for a night full of sparks and inside jokes. And let’s not forget about those little extras: a leather jacket tossed over your shoulders or a pair of ankle boots that make you walk with a little more attitude. These are the pieces that turn a simple outfit into a full-on main character moment, perfect for anyone who wants to make a casual night out feel a little more special.
Casual date night outfits aren’t just for those spontaneous plans with your crush or your ride-or-die bestie—they’re also the go-to choice for gifting when you want to treat someone to a look that’s as versatile as it is stylish. Picture gifting your sister or your BFF a chic mini skirt or a cozy roll neck top; these are the kind of pieces that instantly become wardrobe favorites, ready to be mixed and matched for any low-key adventure. Jumpsuits and slip dresses are the ultimate confidence boosters, easy to dress up with a statement necklace or keep chill with a denim jacket and sneakers. For anyone who wants to keep things classic, a little black dress is always a win—timeless, flattering, and endlessly adaptable. When you’re shopping for casual date night looks, keep an eye out for details that make you smile: a unique neckline, a pop of color, or fabric that feels like a gentle hug. It’s all about curating a closet that’s ready for whatever the night brings, from impromptu concerts to long walks and late-night ice cream runs. And if you ever want to turn up the glam and trade in your jeans for something a little more luxe, check out our curated collection of Elegant Date Night Outfits for those moments when you’re feeling extra.
Every Windsor girl knows that the best memories are made when you’re feeling your absolute best, and that starts with an outfit that lets you own the night. Whether you’re styling wide-leg jeans with a tucked-in tee and layers of jewelry, or reaching for a jumpsuit that makes getting ready a breeze, it’s all about expressing your style and having fun with it. Don’t be afraid to play with textures and silhouettes—mix a mini skirt with a cozy knit, or layer a blazer over a breezy slip dress for that perfect blend of put-together and playful. The key is to choose pieces that make you feel fearless and ready for anything, because every date night—no matter how casual—is a chance to show up as your most confident self. So go ahead and build your dream lineup of casual date night outfits, knowing that whatever you choose, you’ll be serving looks and making memories that last way longer than the last round of fries at your favorite late-night spot.