Vacation Clothing Ideas
Sunshine, sandy toes, and a suitcase full of dreams—it's time to dive into those vacation clothing ideas that are as unforgettable as your next getaway. Whether you're jet-setting to a tropical paradise or planning a chic city escape, every Windsor girl knows the secret to slaying those vacay vibes is all about the right wardrobe. Picture breezy skirts that dance with the ocean breeze, dresses that turn heads faster than a sunset cocktail, and tops that make every moment Instagram-worthy. Your adventure awaits, and with these killer outfit ideas, you'll be living your best life in style. So pack your bags, grab your shades, and let's make some memories!
$38.90
A white sleeveless ribbed knit midi dress featuring a V-neckline and chic high front slit.
$46.90
A vibrant yellow skater dress with a ruffled skirt, halter tie-back, and smocked high waist.
$44.90
A brown cotton-blend romper with a halter plunge neckline and playful skater silhouette.
$44.90
A gold metallic knit maxi dress featuring a plunge cowl halter neckline and adjustable strappy open back.
$20.97 $46.90 55% off
An abstract red knit maxi dress featuring a cowl neckline with hoop trims and a high side slit.
$59.90
An ivory A-line maxi dress featuring gauze fabric, sheer lace insets, and a faux leather belt.
$32.90
A natural crochet maxi skirt featuring a high-rise waist and sultry high front slit.
$42.90
An ivory knit wrap skirt with a tie-waist and cascading fringe hem for a chic getaway look.
$14.97 $34.90 57% off
A pink floral mesh maxi skirt with a high-rise waist and flattering bodycon fit.
$54.90
A denim woven maxi dress featuring a flowy ruffled silhouette, square neckline, and spaghetti straps.
$46.90
A chic black knit jumpsuit featuring a strapless neckline and flattering wide-leg silhouette.
$29.90
An off-white cotton crop top featuring flowy short sleeves, a tie-front, and a flattering V-neckline.
$39.90
A sheer white crochet knit cover-up dress with long sleeves, plunge neckline, and chic hoop insert.
$24.90
An olive tropical crop top with a strappy lace-up back and trendy palm print.
$34.90
A chic brown strapless maxi dress with a high slit and flattering bodycon silhouette.
$44.90
A sultry black floral maxi dress with a V-neckline and form-hugging silhouette, perfect for vacations.
$34.90
A mocha halter jumpsuit featuring a cutout bodice and flattering wide-leg silhouette in stretchy knit.
$38.90
A vibrant pink mini dress featuring a leopard snake print, mesh fabric, side cutout, and ruffled slit.
$39.90
A denim mini skort with a mid-rise adjustable belted waist and form-hugging silhouette.
$9.97 $19.90 50% off
A black tropical print crop top with a plunging V-neckline and ruffled babydoll hem.
$34.90
A sheer mesh zebra print maxi skirt in brown, perfect for vacation or going out.
$29.90
A rust-colored halter crop top in slinky knit fabric perfect for festivals or vacations.
$19.97 $34.90 43% off
A yellow striped knit mini dress featuring a twisted strapless neckline and flattering bodycon silhouette.
$39.90
A breezy ivory lace maxi skirt with a high-rise waist, side slit, and asymmetric hem.
$19.97 $39.90 50% off
A natural paisley-print maxi dress in mesh with a bodycon fit, square neckline, and high side slit.
$49.90
A sultry black knit jumpsuit featuring a cutout bodice and wide-leg silhouette.
$18.97 $44.90 58% off
A strapless blue skort romper with a bodycon fit and flirty skirt overlay for stylish outings.
$26.90
A vibrant orange floral tube top in chiffon with a tie-back detail and stretchy smocked panel.
$34.90
A trendy wide-leg pant in brown abstract print with a flattering high-rise waist.
$14.90
A beige jelly sandal featuring a thong strap, pretty flower accent, and easy open-back design.
$24.90
A brown one-shoulder bikini top with a metallic sheen and sweetheart padded bust.
$39.90
A black tropical print maxi skirt in stretchy knit fabric featuring a high front slit and flowy silhouette.
$29.90
A black tropical print crop top in stretchy knit fabric with long sleeves and a sultry tie-front.
$24.90
A black tropical print maxi skirt in sheer mesh with a high-rise waist and sultry side slit.
$36.90
A natural high-rise mini skort featuring a printed woven overlay, side tie, and stretchy knit shorts lining.
$34.90
An ivory crochet lace kimono with a relaxed fit, perfect for festival or vacation vibes.
$9.97 $56.90 82% off
A floral chiffon romper in natural with a strapless neckline and flattering drop waist seam.
$9.97 $29.90 67% off
A boho chic ivory lace flare pant with a high-rise waist and sheer floral design.
$36.90
A pair of mid-rise denim hot shorts with a color wash tint and cheeky fit.
$32.90
A relaxed off-white linen-blend crop top featuring a collared neckline and button-down front.
$39.90
A black floral mesh maxi skirt featuring a high-rise waist, dramatic front slit, and attached panty lining.
$44.90
A brown tropical-print knit jumpsuit featuring a halter neckline, cutout bodice, and wide-leg silhouette.
$29.90
A black floral mesh crop top featuring long sleeves, a tie-front closure, and an ultra-cropped hem.
$36.90
A denim satin mini dress with a ruched wrap silhouette and spaghetti straps for a chic look.
$42.90
A sleek black knit midi dress with a high slit, cowl neckline, and spaghetti straps.
$59.90
A white mini dress with iridescent sequins, sheer velvet fabric, and adjustable spaghetti straps.
$39.90
An ivory lace romper with a plunging V-neck, open back, and ruffled mini-length overlay.
$59.90
A green satin bodycon mini dress with a sheer lace sequin corset and adjustable straps.
Now Trending
Slay It With Style Mini Skirt in Black
$9.97 $22.90
56% off
Elevate your going-out looks in this sleek faux leather mini skirt! This high-waist mini skirt features a sexy front slit and hidden back zipper for a seamless look at every angle. Make this faux leather mini skirt your wardrobe must-have for date night or clubbing with your party squad. Pair this flirty mini skirt with a beaded bustier top or long-sleeve satin tie-front top for a sexy and fierce night-out look. Fit & FeaturesHigh-rise fit, Vertical seam details, back zipper, Front slit accent, Form-hugging fit, Mini-length hem, Unlined faux leather fabric, minimal stretch, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Slay It With Style Mini Skirt in Black | Size: L | Leather/Satin Fabric
Channel your western side with this trendy-chic skirt that will level up your festival look! It features a high-rise waist, an asymmetric mini-length hem with a form-hugging fit, and long fringe detailing that cascades to your ankles. The stylish fringe design will dance with you to your favorite band! Complete your 'fit with a cropped graphic tee and cowboy boots. Fit & FeaturesHigh-rise waist, Back zipper, hook and eye closure, Asymmetric mini-length hem, Form-hugging fit, Long fringe design, ankle-length hem, Faux suede fabric, moderate stretch, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Wild At Heart Long Fringe Skirt in Tan | Size: XS | Faux Suede
Windsor Cute And Trendy Cargo Mini Skirt in Dark Denim-2
$13.97 $34.90
60% off
This cute and trendy cargo mini skirt will step up this season's 'fits! It features a mid-rise waist, an included removable belt with a double grommet design, cargo-style side pockets, a mini-length hem, and a fitted silhouette. The denim fabric offers a moderate stretch. Style this denim skirt with a crop top and clear mules. Fit & FeaturesMid-rise waist, hidden front buttons, zipper closure, Included removable belt, double grommet design, Dual cargo-style side pockets, Mini-length hem, Fitted silhouette, Denim fabric, moderate stretch, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Cute And Trendy Cargo Mini Skirt in Dark Denim-2 | Size: S
Fit & FeaturesStretchy smooth knit-lined fabrication, High-rise fit, Ruching, Asymmetrical high-side slit, Midi length hem, Runs true to size, Shop Matching Crop Top: Bold Staple Long Sleeve Crop Top Free Shipping on All Orders Over $75. | Windsor Bold Staple Ruched Asymmetrical Midi Skirt in Black | Size: XS
Level up your sleek status with this chic mini skirt made with smooth faux leather fabric to elevate your casual 'fits. It features a high-rise waist, a side slit accent at the hem, and a form-hugging silhouette to highlight your stunning curves. Fit & FeaturesFaux leather fabric, plenty of stretch, High-rise elasticized waist, Side slit, Mini-length hem, Form-hugging fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sleek Status Faux Leather Mini Skirt in Black | Size: S
Step out looking like goals in this micro mini skirt with a flirty side slit and bodycon fit that'll get you noticed! Fit & FeaturesStretchy knit fabric, High-rise waist, Side slit, Bodycon silhouette, Micro mini-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor First Take Micro Slit Mini Skirt in Black | Size: L | Knit Fabric
Make a statement in this lace slit maxi skirt. With sheer lace, ruching, and a high slit, it's your go-to for that effortlessly chic vibe. Fit & FeaturesSheer lace fabric with mini-length knit lining, plenty of stretch, High-rise waist, Ruching, High front slit, Maxi-length hem, Flowy silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Keep A Secret Lace Slit Maxi Skirt in Black | Size: M | Lace Fabric/Knit Fabric/Sheer Lace Fabric
Channel an effortless boho vibe in this breezy sheer lace maxi skirt featuring a high-rise waist, ruched detailing with an adjustable drawstring, a high-cut side slit, and an asymmetric hem with a flowy silhouette. Perfect for pairing with a crop top and booties. Fit & FeaturesSheer lace fabric with mini-length knit lining, plenty of stretch, High-rise waist, Ruching, adjustable drawstring, High side slit, Asymmetric maxi-length hem, Flowy fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Breezy Boho Sheer Lace Asymmetric Maxi Skirt in Ivory | Size: M | Lace Fabric/Knit Fabric/Sheer Lace Fabric
Heading on vacation? Don't forget to grab this vacay ready high-rise crochet maxi skirt with a sultry high front slit that flaunts some leg. Pair with the matching top and your fave shades! Fit & FeaturesCrochet fabric, stretchy knit lining, High-rise elasticized waist, High front slit, Flowy maxi-length silhouette, Runs true to size , Shop The Matching Top: Vacay Ready Tie-Front Bandea Crochet Crop Top Free Shipping on All Orders Over $75. | Windsor Vacay Ready High Rise Crochet Maxi Skirt in Natural | Size: L | Knit Fabric
Call Me Cutie Floral Eyelet Mini Skirt in White
$16.97 $39.90
57% off
Get ready for everyone to call you cute in this floral mini skirt designed with a flirty layered ruffle that captures attention and a mini-length hem that lets you flaunt your figure. Pair with the matching top. Shop Matching Top: Call Me Cutie Lace-Up Floral Eyelet Corset TopFit & FeaturesFloral print, eyelet woven lined fabric, Stretchy smocked high-rise waist, Layered ruffle , Mini-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Call Me Cutie Floral Eyelet Mini Skirt in White | Size: L
Vacation Clothing Ideas
When it comes to packing for a getaway, your suitcase is basically your passport to feeling like the main character—so make every piece count. Whether you’re jet-setting to a tropical paradise, road tripping with your besties, or planning a dreamy staycation, the secret sauce is all about mixing comfort with confidence. Think breezy linen sets that keep you cool from sunrise to golden hour, cotton tees that play nice with literally everything, and wide-leg pants that move with you as you chase sunsets or last-minute dinner reservations. The real MVPs are those versatile pieces you can style up or down, turning a late-night adventure into an impromptu photo shoot. And don’t even get us started on accessories—oversized sunnies, statement earrings, and a swipe of bold lip color can take your look from “just landed” to “where’s the afterparty?” faster than you can say “out of office.”
If you’re shopping for yourself (because self-love is always in style) or looking for the perfect gift for your ride-or-die, vacation clothing ideas are the ultimate game-changer. Imagine gifting your BFF a matching set that’s made for poolside lounging and spontaneous brunches, or surprising your sister with a flowy dress that’ll have her twirling through every Insta story. Windsor vacation outfits are made for those who want to own every moment—whether you’re exploring a new city, dancing under the stars, or just soaking up good vibes with your crew. Prioritize lightweight, breathable fabrics that keep you feeling fresh, even when the group chat dares you to take on a full day of exploring. And don’t underestimate the power of layers; a denim jacket or a slouchy cardigan is your ticket to surviving chilly flights or breezy nights without missing a beat. Shoes? Go for comfort-meets-style: think cute slip-ons for airport sprints and sandals that can handle both boardwalk strolls and rooftop cocktails.
Packing for a trip is your chance to curate a wardrobe that feels as adventurous as your itinerary. Start with a foundation of neutral colors for easy mixing and matching, then add pops of personality with bold prints, vibrant accessories, or a killer pair of shades. The best vacation looks are the ones that make you feel unstoppable—ready for a day of sightseeing, a spontaneous dip in the pool, or a night out that turns into morning. If you’re looking to level up your wanderlust wardrobe, check out our curated picks for Stylish Vacation Wear and get inspired to pack like a pro. No matter where your travels take you, remember: you’re not just dressing for the destination—you’re dressing for the memories you’re about to make.