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.
$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.
$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.
$32.90
A sultry black knit halter top featuring a plunge lace trim neckline and flattering corset bodice.
$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.
$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.
$19.97 $34.90 43% off
A sleek pink knit mini dress featuring a ruched bust, off-the-shoulder neckline, and bodycon silhouette.
$42.90
A black crepe mini dress featuring a crew neck, front pleating, and a flattering bodycon silhouette.
$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.
$26.90
A stylish black halter crop top with a knotted bust and smooth stretchy knit fabric.
$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.
$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.
$44.90
A black floral maxi dress featuring sheer mesh, a lace-up strappy back, and a form-hugging silhouette.
$39.90
A denim mini skort with a mid-rise adjustable belted waist and form-hugging silhouette.
$39.90
A black stretchy mini dress featuring a halter plunge neckline, front cutout, and bodycon silhouette.
$46.90
A sultry black jumpsuit featuring a cowl halter neckline, cutout back, and wide-leg silhouette.
$32.90
A black mini bodycon dress with a sweetheart neckline and dramatic ruched bell sleeves.
$44.90
A strapless white mini dress in pleated ponte knit fabric with a form-hugging bodycon silhouette.
$59.90
A white lace mini dress with faux pearl embellishments and adjustable spaghetti straps for elegant outings.
$39.90
A sultry black romper featuring a plunge halter neckline and ruffled short hem in stretchy knit fabric.
$42.90
A denim blue knit bodycon midi dress featuring a cutout back, twist straps, and a side slit.
$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.
$44.90
A chic black mesh and satin short dress with sheer sleeves and an alluring back cutout.
$20.97 $46.90 55% off
An olive green gauze skater dress featuring V-neck cutouts, flowy sleeves, and a breezy silhouette.
$49.90
A brown mesh maxi dress featuring a bold floral print, drapey cowl halter neckline, and curve-hugging fit.
$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.
$49.90
An off-the-shoulder black midi dress featuring mesh-lined fabric, ruched bodycon silhouette, and a bold side slit.
$36.90
A black nylon mini dress featuring a fitted A-line silhouette, square neckline, and hidden shorts.
$34.90
A sage mesh midi dress featuring a cowl neckline, ruched sides, and adjustable tie-back straps.
$39.90
A sleek black knit midi dress featuring a ruched bodycon silhouette, sleeveless V-neckline, and spaghetti straps.
$21 $29.90 30% off
A sleek black knit bodycon mini dress with an asymmetric neckline and waist cutout.
$34.90
A sage acid-wash denim skort with a mid-rise waist, statement pockets, and a flattering bodycon fit.
$29.90
A sheer black mesh top with floral print, ruffled edges, lace trim, and a flirty tie-front.
$36.90
A high-rise denim skort with front patch pockets and stretchy knit shorts lining for all-day comfort.
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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 Pink | Size: L | Knit Fabric/Mesh Fabric/Mesh Fabric
The Lucy mini party dress is sleek and simple from the front and stunning from the back. Turn heads as you stun from the back with a flirty big bow tie with a dramatic train that glides against the floor! Fit & FeaturesTaffeta structured woven-lined fabric, slight stretch, Strapless, square neckline, non-slip grip, Hidden side zipper, hook and eye closure, Front and back pleating and ruching, Form-hugging, mini-length hem, Detachable back bow with train, Runs true to size, Where to Wear:Homecoming, weddings, brides, bachelorettes, big birthday events, fancy date nights, gorgeous dinner parties, cocktail soirees, rehearsal dinners, engagement photoshoots and parties Free Shipping on All Orders Over $75. | Windsor Lucy Taffeta Bow Mini Party Dress in White | Size: XS
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: L | Knit Fabric
This satin mini dress will be your favorite for celebrations, events, and date nights! Sleek and smooth satin shapes this off-the-shoulder dress, which features a flattering A-line silhouette perfect for styling with heels. Fit & FeaturesSmooth and sleek satin fabric, stretchy knit lining, Off-the-shoulder neckline, Short sleeve cuffs, A-line silhouette, Mini-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Classics Lover Off-The-Shoulder Satin A-Line Mini Dress in White | Size: L | Knit Fabric/Satin Fabric
Express your devotion to romance in the Lena mesh mini dress perfect for modern brides, birthday girls, or graduates! The strapless cowl neckline adds a touch of elegance, while the bodycon fit accentuates your figure. Fit & FeaturesBeaded mesh fabric, stretchy knit lining, Strapless cowl neckline, Back zipper and hook-eye closure, Bodycon fit, mini-length hem, Runs true to size, Where to Wear:Prom, date nights, bachelorettes, girl's night out, birthdays Free Shipping on All Orders Over $75. | Windsor Lena Strapless Bodycon Beaded Mesh Mini Dress in White | Size: M | 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: M | Knit Fabric
Bling on the sultry glamour with the sparkling details of the stunning Catalina formal mini dress with a bodycon silhouette that will flaunt your gorgeous figure! Fit & FeaturesSheer mesh fabric, full-length knit lining, plenty of stretch, Mini iridescent rhinestones, faux pearl embellishments, Sleeveless cowl neckline, Adjustable spaghetti straps, Mini-length hem, bodycon silhouette, Runs true to size, Where to Wear:Prom, bachelorettes, birthdays, girl's night out, date nights Free Shipping on All Orders Over $75. | Windsor Catalina Rhinestone And Pearl Formal Mini Dress in White | Size: M | Knit Fabric/Rhinestone/Mesh Fabric
Show off a flawless allure in this figure-flaunting mini dress! Designed with a sleek knit fabric with a fab sheen, this mini-length dress offers plenty of stretch so you can dance all night. The sleeveless bodice is shaped with a pleated cowl neckline for a chic draped effect and spaghetti straps. The pleating across the bodycon silhouette will accentuate your stunning curves. Style with metallic heels for a club night out.Fit & FeaturesStretchy sleek knit fabric, Sleeveless pleated cowl neckline, Spaghetti straps, Pleating, Bodycon fit, Strapless or sticky bra recommended, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Flawless Allure Cowl Neck Bodycon Mini Dress in Pink | Size: L | Knit Fabric
Keep it sophisticated with a satin mini dress that radiates luxe. The dress features a sleeveless square neckline, detachable rhinestone embellished spaghetti straps, ruched side and back seams, and a form-hugging silhouette and mini-length hem. Complete look with rhinestone heels and a satin clutch. Fit & FeaturesSleeveless square neckline, Detachable rhinestone spaghetti straps, Ruched side and back seams, Form-hugging silhouette, Mini-length hem, Lined sleek satin fabric, moderate stretch, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Stunning Sophistication Rhinestone Mini Dress in Wine | Size: M | Rhinestone/Satin Fabric
Make yourself known in this satin mini dress as you step into the club or party! The short dress is designed with a strapless neckline with non-slip grip lining, a pleated bust and side seam, a flattering bodycon silhouette, and a mini-length hem. Style the satin dress with rhinestone heels for a charming sparkle! Fit & FeaturesStrapless neckline, non-slip grip lining, Pleated bust and side seam, Bodycon silhouette, Mini-length hem, Silky satin fabric, minimal stretch, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Make It Known Satin Strapless Pleat Mini Dress in Pink | Size: L | Rhinestone/Satin Fabric
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.