Casual Vacation Outfits
Sunshine, palm trees, and a whole lot of chill vibes—sounds like the perfect getaway, right? Whether you're jet-setting to a tropical paradise or hitting up a cozy cabin retreat, nailing that effortlessly chic look is a must. Enter: casual vacation outfits that scream laid-back luxe without breaking the bank. Think breezy dresses that dance with the ocean breeze, flirty skirts perfect for sunset strolls, and tops that keep you cool while turning up the heat. It's all about packing those versatile pieces that let you mix, match, and slay every day of your vacay. Grab your sunnies, girl, because these looks are ready to make waves!
$44.90
A black one-shoulder tropical maxi dress with a ruffled slit and metal-accented strap.
$46.90
A pink knit maxi dress featuring a halter neckline, bodycon fit, and an alluring lace-up back.
$32.90
A natural crochet maxi skirt featuring a high-rise waist and sultry high front slit.
$36.90
A sheer crochet kimono in natural with slouchy sleeves and an open front design.
$46.90
An ivory striped midi dress with cutouts, adjustable straps, and dual side slits for casual elegance.
$42.90
An ivory knit wrap skirt with a tie-waist and cascading fringe hem for a chic getaway look.
$29.90
An off-white cotton crop top featuring flowy short sleeves, a tie-front, and a flattering V-neckline.
$32.90
A pair of white mid-rise denim shorts with distressed accents and a form-hugging fit.
$34.90
A chic strapless brown maxi dress with a high slit and flattering bodycon silhouette.
$34.90
A mocha halter jumpsuit featuring a cutout bodice and flattering wide-leg silhouette in stretchy knit.
$35.90
An olive green tropical print mini dress featuring a V-neckline, twisted bust, and strappy tie-back.
$32.90
A natural crochet knit mini dress featuring a strapless neckline, side slit, and bodycon silhouette.
$44.90
A rust-colored one-shoulder maxi dress with a tropical print, side cutout, and high slit.
$49.90
A sultry black knit jumpsuit featuring a cutout bodice and wide-leg silhouette.
$42.90
A navy blue paisley skater dress with a halter V-neckline and playful tie-back design.
$49.90
A brown mesh maxi dress featuring a bold floral print, drapey cowl halter neckline, and curve-hugging fit.
$39.90
A natural paisley-print mesh maxi dress featuring a bodycon silhouette, square neckline, and high side slit.
$42.90
A strapless ivory knit romper featuring a vibrant floral print, ruffled hem, and form-hugging fit.
$44.90
A strapless blue skort romper with a bodycon fit and flirty skirt overlay for stylish outings.
$39.90
A natural striped knit mini dress featuring a flirty cutout back and bodycon fit.
$19.90
A black tropical print crop top with a plunging V-neckline and ruffled babydoll hem.
$19.90
A natural crochet bandeau crop top with a tie-front closure, perfect for vacation or festivals.
$29.90
A white high-rise denim skort with a faux wrap-front, hidden shorts, and minimal-stretch cotton blend.
$24.90
A trendy brown abstract crop top with flowy short sleeves and a flattering tie-front design.
$44.90
A mint crochet mini dress featuring a beaded halter neckline, cutout front, and bodycon silhouette.
$46.90
A sage green mini dress featuring a halter neckline, ruffled skater silhouette, and airy woven fabric.
$49.90
An olive green gauze skater dress featuring a tie-front, ruffled tiers, and adjustable spaghetti straps.
$38.90
A sultry orange knit midi dress featuring a one-shoulder neckline, front cutouts, and gold O-ring accents.
$46.90
A natural knit maxi dress featuring a bold tropical leaf print, one-shoulder cutout, and gold hardware.
$34.90
A yellow striped knit mini dress featuring a twisted strapless neckline and flattering bodycon silhouette.
$44.90
A sultry black floral maxi dress with a V-neckline and form-hugging silhouette, perfect for vacations.
$32.90
A pair of ivory sheer woven palazzo pants with a wide-leg silhouette and adjustable tie-front drawstring.
$46.90
A bold ivory maxi tube dress in lightweight woven fabric, featuring a geometric print, fringe trim, and side slit.
$42.90
A royal blue maxi dress featuring a tropical print, lace-up back, and high side slit in stretchy knit.
$9.97 $22.90 56% off
A black and white tropical tie front crop top with fluttery sleeves and palm print knit fabric.
$44.90
A brown tropical print knit jumpsuit featuring a halter neckline, cutout bodice, and wide-leg silhouette.
$29.90
A vibrant mesh crop top featuring a tropical print, tie-front design, and long bell sleeves.
$24.90
A tropical print maxi skirt in black mesh with a high-rise waist and sultry side slit.
$28.90
A black gauze midi dress featuring a flowy silhouette, V-neckline, adjustable straps, and hidden side pockets.
$44.90
A flowy green gauze midi dress featuring a strapless smocked bodice and tiered A-line silhouette.
$56.90
A natural floral chiffon romper featuring a strapless neckline and flattering drop waist seam.
$38 $46.90 19% off
A chic black and white pinstripe romper with floral lace straps and a pleated skater skirt.
$34.90
A sheer black chiffon kimono featuring relaxed sleeves and a tie-front for effortless vacation layering.
$42.90
A sultry taupe jumpsuit with a tropical print, featuring a cutout design and wide-leg silhouette.
$42.90
A blue paisley halter mini dress featuring a smocked bust, open tie-back, and ruffled skater silhouette.
$32.90
A relaxed off-white linen-blend crop top featuring a collared neckline and button-down front.
$54.90
A breezy natural linen-blend maxi dress featuring a halter neckline, open tie back, and high side slit.
$46.90
A blue gauze skater dress featuring a halter neckline, cutout bodice, and ruffled mini 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
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
Bring the dazzling glamour to the party in this long sleeve rhinestone mesh mini dress! Designed with a stretchy sheer mesh fabric with a partial knit lining, the mini-length dress is accented with all-over rhinestone embellishments for a gorgeous and chic shine. The square neckline shapes the bodice, and the unlined long sleeves have slit accents and flare out for a trendy look. The bodycon silhouette will hug your gorgeous curves. Style this mini dress with rhinestone heels for all the more sparkle. Fit & FeaturesStretchy sheer mesh fabric, partial knit lining, Rhinestone embellishments, Square neckline, Long bell sleeves with slit detail, Back zipper, hook and eye closure, Bodycon fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Dazzling Glam Long Sleeve Rhinestone Mesh Mini Dress in Navy Blue | Size: XS | Knit Fabric/Rhinestone/Mesh 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
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 Coral | Size: XL | Knit Fabric/Mesh Fabric/Mesh Fabric
Casual Vacation Outfits
When it comes to packing for that long-awaited getaway, the Windsor girl knows the vibe is all about effortless style with a side of main character energy. Whether you’re jetting off to a dreamy destination or just planning a staycation with your besties, casual vacation outfits are your golden ticket to looking cute without trying too hard. Think easy-breezy dresses that move with you, flowy skirts that catch the breeze (and a few eyes), and tops that go from brunch to boardwalk without missing a beat. It’s all about pieces you can mix, match, and throw on in five minutes—because who has time to stress over an outfit when there are adventures waiting? These are the kinds of looks that work for exploring hidden gems in a new city, grabbing spontaneous coffee runs, or just living your best life poolside with a cold drink in hand. And let’s be real: nothing says “I’m on vacay” like an outfit that makes you feel like you could star in your own travel montage.
For the girls who love to gift their ride-or-die squad, casual vacation outfits are the ultimate way to say, “I see you, and you deserve a little getaway glam.” Maybe your BFF just landed her dream internship and needs a wardrobe upgrade for her celebratory trip, or your sister’s been manifesting a girls’ weekend and you want to surprise her with something she’ll actually wear. These pieces are not just about looking good—they’re about feeling free, confident, and totally in the moment. Imagine stepping out for golden hour photos, your outfit catching the last rays of sunlight as you laugh with your crew, everyone hyped up and living their best lives. That’s the magic of a well-chosen casual look: it’s a mood, a memory, and a little bit of mischief all rolled into one. And if your plans include sandy toes and salty air, don’t miss our curated collection of Casual Beach Outfits for even more inspo that brings the heat.
No matter where you’re headed or who you’re with, the right casual vacation outfits are your secret weapon for making every moment Insta-worthy. Prioritize lightweight fabrics that keep you cool when things heat up, silhouettes that let you move (because dance breaks are mandatory), and details that make you feel like the best version of yourself. These are outfits that work hard for you, whether you’re hopping between cute cafes, exploring local markets, or just catching up with friends on a rooftop with killer views. The best part? Every piece is designed to be worn again and again, long after your vacay glow fades—because the Windsor girl’s energy is too good to save for special occasions. Go ahead, treat yourself (and your squad) to styles that turn every day into a highlight reel.