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!
$59.90
A white woven maxi dress featuring a floral print, open tie back, and ruffled silhouette.
$44.90
A black one-shoulder tropical maxi dress with a ruffled slit and metal-accented strap.
$32.90
A natural crochet maxi skirt featuring a high-rise waist and sultry high front slit.
$46.90
A pink knit maxi dress featuring a halter neckline, bodycon fit, and an alluring lace-up back.
$46.90
An ivory striped midi dress with cutouts, adjustable straps, and dual side slits for casual elegance.
$36.90
A sheer crochet kimono in natural with slouchy sleeves and an open front design.
$42.90
An ivory knit wrap skirt with a tie-waist and cascading fringe hem for a chic getaway look.
$39.90
A sheer white crochet knit cover-up dress featuring a plunge neckline, hoop insert, and long flared sleeves.
$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.
$44.90
A rust-colored one-shoulder maxi dress with a tropical print, side cutout, and high slit.
$32.90
A natural crochet knit mini dress featuring a strapless neckline, side slit, and bodycon silhouette.
$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.
$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.
$42.90
A strapless ivory knit romper featuring a vibrant floral print, ruffled hem, and form-hugging 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.
$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.
$44.90
A mint crochet mini dress featuring a beaded halter neckline, cutout front, and bodycon silhouette.
$38.90
A sultry orange knit midi dress featuring a one-shoulder neckline, front cutouts, and gold O-ring accents.
$44.90
A sultry black floral maxi dress with a V-neckline and form-hugging silhouette, perfect for vacations.
$46.90
A natural knit maxi dress featuring a bold tropical leaf print, one-shoulder cutout, and gold hardware.
$32.90
A pair of ivory sheer woven palazzo pants with a wide-leg silhouette and adjustable tie-front drawstring.
$34.90
A yellow striped knit mini dress featuring a twisted strapless neckline and flattering bodycon silhouette.
$42.90
A taupe tropical print maxi dress featuring mesh fabric, a one-shoulder neckline, and chic O-ring detail.
$39.90
A natural paisley-print mesh maxi dress featuring a bodycon silhouette, square neckline, and high side slit.
$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.
$9.97 $22.90 56% off
A black and white tropical tie front crop top with fluttery sleeves and palm print knit fabric.
$42.90
A royal blue maxi dress featuring a tropical print, lace-up back, and high side slit in stretchy knit.
$24.90
A tropical print maxi skirt in black mesh with a high-rise waist and sultry side slit.
$34.90
A sheer black chiffon kimono featuring relaxed sleeves and a tie-front for effortless vacation layering.
$38 $46.90 19% off
A chic black and white pinstripe romper with floral lace straps and a pleated skater skirt.
$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.
$42.90
A sultry taupe jumpsuit with a tropical print, featuring a cutout design and wide-leg silhouette.
$46.90
A blue gauze skater dress featuring a halter neckline, cutout bodice, and ruffled mini hem.
$32.90
A relaxed off-white linen-blend crop top featuring a collared neckline and button-down front.
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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: 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 Vacation Outfits
Vacay mode: activated. When you’re planning your next getaway, every Windsor girl knows the real adventure starts with curating a suitcase full of casual vacation outfits that can handle every spontaneous detour and TikTok-worthy moment. Whether you’re jetting off to a dreamy coastal town, road-tripping with your ride-or-die crew, or just living your best life at a staycation hotspot, the vibe is all about keeping things effortlessly cute without sacrificing comfort. Think airy fabrics that let the breeze do its thing, playful silhouettes that move with you from brunch to beach bonfire, and those little details—like a flirty tie-back or a cheeky cut-out—that turn a basic look into something totally main-character energy. Every outfit should feel like a passport stamp: a little memory you can wear, whether you’re sipping iced lattes on a sun-drenched patio or chasing golden hour with your besties. The best casual vacation pieces are the ones you can throw on without overthinking, knowing you’ll look fire in every selfie and feel ready for whatever the day throws at you (impromptu dance party, anyone?).
Packing for a getaway is basically an Olympic sport, and your wardrobe should be as flexible as your itinerary. That’s why it’s all about mixing and matching—think flowy skirts that double as beach cover-ups, tops that go from daytime exploring to rooftop dinners, and dresses that make you feel unstoppable whether you’re snapping pics for the ‘gram or just living in the moment. Layering is your secret weapon: a lightweight button-down tossed over a tank, a cropped denim jacket for those breezy nights, or a statement accessory that pulls the whole look together. And let’s not forget, these pieces aren’t just for you—casual vacation outfits make the ultimate gift for your travel-obsessed BFF, your sister who’s always planning her next escape, or anyone who deserves a little extra sunshine in their closet. Because let’s be real, giving the gift of a killer outfit is basically giving the gift of confidence, and who doesn’t want their best girl to feel like a total icon?
No matter where your wanderlust takes you, the magic of a well-chosen casual vacation outfit is how it adapts to every adventure—whether you’re exploring hidden gems in a new city, lounging poolside with a mocktail in hand, or making memories on a spontaneous road trip. Comfort is non-negotiable, but style? That’s where you get to show off your personality and set the tone for your trip. If you’re all about that sunkissed, toes-in-the-sand aesthetic, you’ll want to check out our curated picks for Casual Beach Outfits—packed with easy-breezy looks that are basically made for salty hair and sunlit selfies. So go ahead, pack your bags with pieces that spark joy, bring the good vibes, and make every day feel like a getaway. You deserve to look and feel unstoppable, wherever the journey takes you.