Casual Summer Date Outfits
Ready to serve looks and steal hearts? Casual summer date outfits are your ticket to effortless charm, flirty vibes, and a little main-character energy—because who says you can't be comfy and totally crush-worthy at the same time? Whether it’s rooftop drinks or a spontaneous ice cream run, these styles are made for turning “just hanging out” into “can’t stop thinking about her.” Go ahead, make every date one for the group chat.
$34.90 - $42.90
A black crepe jumpsuit with a plunging V-neckline, midriff cutout, and halter neck design.
$46.90
A black strapless romper with rhinestone embellishments, offering a form-hugging silhouette and high waist.
$39.90
A trendy ivory lace romper with a plunging V-neck and ruffled mini-length overlay.
$64.90
A sage skater dress with a lace-up back, ruched bust, and tiered A-line silhouette.
$32.90
A brown strapless mini dress featuring ruched sides, a ruffled hem, and soft brushed knit fabric.
$48.90
A flirty white mini skater dress featuring a breezy eyelet knit and charming tie-back detail.
$89.90
A yellow mini dress with faux pearl embellishments, halter cowl neckline, and bodycon fit.
$39.90
A black knit romper featuring polka dots, a strapless neckline, and tiered ruffled overlay.
$32.90
A breezy white eyelet knit skater dress featuring a square neckline and double-layered flared skirt.
$44.90
A yellow crochet knit midi dress featuring a high halter neckline and form-hugging silhouette.
$46.90
An adorable white eyelet mini dress with a flirty tie-back and ruffled A-line silhouette.
$34.90
An off-white sheer lace mini skort featuring a drop waist and tiered ruffled overlay with hidden shorts.
$49.90
A yellow eyelet skater dress featuring a V-neckline, adjustable spaghetti straps, and a tie-back design.
$46.90
An olive green gauze skater dress featuring V-neck cutouts, flowy sleeves, and a breezy silhouette.
$34.90
A chic strapless brown maxi dress with a high slit and flattering bodycon silhouette.
$46.90
A natural crochet maxi dress featuring a bodycon fit, V-neckline, and open lace-up back.
$34.90
A mocha halter jumpsuit featuring a cutout bodice and flattering wide-leg silhouette in stretchy knit.
$34.90
A strapless red-brown knit midi dress featuring side ruching, a bodycon silhouette, and a side slit.
$49.90
A navy blue mini skater dress featuring sequin lace trim, adjustable straps, and a lace-up back.
$44.90
A natural ribbed knit midi dress featuring a bold cutout bodice, side slit, and bodycon silhouette.
$35.90
An olive green tropical print mini dress featuring a V-neckline, twisted bust, and strappy tie-back.
$39.90
A striped knit mini dress in natural with a flirty cutout back and bodycon fit.
$39.90
A brown mesh mini dress featuring a strapless neckline, side cutout, and ruffle-trim slit.
$32.90
A natural crochet knit mini dress featuring a strapless neckline, side slit, and bodycon silhouette.
$49.90
A brown mesh maxi dress featuring a bold floral print, drapey cowl halter neckline, and curve-hugging fit.
$32.90
A sheer black crochet mini dress featuring a halter V-neckline, wooden beaded accents, and bodycon silhouette.
$49.90
A denim chambray romper featuring floral embroidery, a ruched bust, smocked back, and flowy shorts.
$36.90
A sultry brown knit midi dress featuring a lace-up back, ruched bodycon fit, and side slit.
$44.90
A yellow skater dress featuring eyelet lace embroidery and a stretchy smocked bodice.
$49.90
A playful denim skater dress featuring a halter neckline, bust cutout, drop waist, and pleated silhouette.
$49.90
A strapless denim mini dress featuring a front lace-up detail and curve-hugging bodycon silhouette.
$34.90
A yellow striped knit mini dress featuring a twisted strapless neckline and flattering bodycon silhouette.
$34.90
A navy blue ribbed knit strapless mini dress featuring an A-line silhouette and high-stretch comfort.
$29.90
A sheer brown floral lace top featuring a V-neck, tie-front, and flared long sleeves.
$42.90
A rust floral skater dress in airy rayon with tie-back halter straps and an open back.
$49.90
An airy white eyelet skater dress featuring a lace-up bust, lace trim, and adjustable tank straps.
$35.90
A strapless white floral midi dress with a form-hugging fit and chic flared hem.
$28.90
A breezy black midi dress featuring gauze fabric, a V-neck, adjustable straps, and hidden side pockets.
$44.90
A flowy green gauze midi dress featuring a strapless smocked bodice and tiered A-line silhouette.
$46.90
A blue gauze skater dress featuring a halter neckline, cutout bodice, and ruffled mini hem.
$42.90
A flirty natural eyelet knit mini dress featuring ruffled trims, a plunging V-neck, and open tie-back.
$38.90
A vibrant multi-color tie-dye mesh mini dress featuring a plunge halter neckline and playful ruffle trims.
$54.90
A denim woven maxi dress featuring a flowy ruffled silhouette, square neckline, and spaghetti straps.
$42.90
A light blue gingham skater dress featuring a smocked waist, sweetheart neckline, and adjustable straps.
$34.90
A black and white gingham crop top featuring a square neckline, mini bows, and adjustable spaghetti straps.
$42.90
A white woven romper featuring a plunge halter neckline, smocked waist, and flowy silhouette for chic style.
$36.90
A high-rise denim skort with front patch pockets and stretchy knit shorts lining for all-day comfort.
$52.90
A light blue strapless mini dress featuring eyelet fabric, a smocked bodice, and a ruffled hem.
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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: L | 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: M | 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
Casual Summer Date Outfits
When it comes to nailing the vibe for a casual summer date, it’s all about easy-breezy style that lets you move, laugh, and flirt without a care in the world. Think about that golden hour glow, the kind that makes everything look like it’s straight out of a rom-com—and you’re the main character, obviously. The key is to pick pieces that feel as good as they look: lightweight, breathable fabrics like cotton, linen, and soft denim are total game-changers when the temps are up and the plans are spontaneous. Whether you’re heading for iced coffee on a sun-dappled patio, catching an outdoor movie, or strolling through a night market, comfort is non-negotiable. You want to be able to kick off your shoes, sit cross-legged on a picnic blanket, or dance down the sidewalk without a second thought. That’s why relaxed fits, flowy silhouettes, and shoes you can actually walk in are the MVPs of any summer date lineup. And let’s not forget those little details that take your look from “cute” to “can’t-stop-staring”—a pop of color in your jewelry, a playful hair scarf, or a pair of sunnies that make you feel like a celeb dodging paparazzi.
Picking out a casual date outfit isn’t just about following trends; it’s about finding something that feels like *you*, only with a little extra sparkle. For some, that might mean a flirty sundress that twirls with every step, paired with sandals made for walking (or running, if you’re late and have to make a dramatic entrance—hey, it happens). For others, it’s all about denim shorts and a top that says “I woke up like this” but in the best way possible. And if you’re the type who loves a one-and-done look, rompers and matching sets are basically your fairy godmothers. These picks aren’t just cute—they’re practical, too, letting you go from brunch to beach to rooftop drinks without missing a beat. Plus, if you’re shopping for a gift (maybe for your bestie who just landed a first date or your sister who’s living her main character moment), these styles are total crowd-pleasers. They’re the kind of pieces that get worn on repeat, popping up in group chat selfies and Insta stories all summer long. And if you’re craving more inspo or want to level up your date night game, don’t sleep on our Casual Date Night Outfits page for even more looks that’ll have you feeling unstoppable.
No matter where your plans take you—picnic in the park, sunset by the water, or a last-minute ice cream run—the right outfit is your secret weapon. It’s your confidence boost, your conversation starter, and your ticket to making memories that’ll have you grinning for weeks. The best part? These casual summer date outfits are designed to keep up with every adventure, big or small. So go ahead, mix and match, play with accessories, and make every look your own. You deserve to feel amazing, whether you’re out with someone special or just treating yourself to a little extra sunshine.