Vacation Looks
Vacation dressing should be easy, stylish, and ready for wherever the day takes you. Start with mini sundresses and flirty rompers that work for both sightseeing and rooftop drinks at sunset. Add in flowy maxis, crochet cover-ups for poolside sunbathing, and sleek sunnies that instantly pull a look together. From cutoff denim shorts to swimwear with eye-catching details, these outfits keep your suitcase light and your style on point for every getaway moment.
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Vacation Dresses & Outfits for Effortless Getaways
Pack light and look luxe in vacay dresses and vacation outfits designed for sun-soaked escapes. Whether you’re poolside at a beach resort or exploring cobblestone streets, Windsor’s resortwear blends breezy fabrics, relaxed silhouettes, and bold prints for travel outfits you’ll want to wear on repeat.
Easy, Packable Styles
Slip into breezy maxi dresses in tropical prints or neutral tones—white, ivory, and tan—for instant cruisewear elegance. Chic rompers and vacay outfits like matching top-and-bottom sets in airy cotton or linen make packing a breeze and styling stress-free.
Day-to-Night Versatility
Transition from sunrise yoga to sunset cocktails in flowy sundresses or relaxed separates. Mix and match colorful vacation-ready separates—think high-waist shorts with off-shoulder tops—or choose effortless travel outfits in knit jumpsuits and wrap skirts that go anywhere.
Resort & Beach Essentials
Complete your look with stylish bikinis under sheer cover-up dresses or mesh tunics. Add slide sandals, statement sunglasses, and a woven tote for poolside chic. From beach days to rooftop lounges, these vacay dresses keep you feeling confident and carefree.
Ready to jet off in style? Explore Windsor’s full collection of vacation dresses and outfits online, in-app, or at your nearest Windsor store.
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Seas The Day Pearl and Charm Statement Necklace
Giving total mermaid-on-vacay energy—and we’re obsessed. This pearl and charm necklace brings soft glam with a splash of beachy vibes, perfect for brunch plans or sunset selfies.
Fit & Features
- Faux pearl and charms
- Long chain
- Lobster clasp closure
Style Number/Barcode: 07002-000143
Category Name: Vacation Looks
Price: $3.97 $9.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Alluring Marble Mesh Bodycon Dress
This alluring marble mesh bodycon dress will draw all the attention your way! It features a square neckline, sheer long fitted sleeves, a short, curve-hugging silhouette, and an all-over marble swirl pattern. The partially lined mesh fabric offers plenty of stretch. Style with platform heels.
Fit & Features
- Square neckline
- Sheer long fitted sleeves
- Mini-length hem
- Fitted bodycon silhouette
- Marble swirl pattern
- Sheer mesh fabric, partial knit lining, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4863
Category Name: Vacation Looks
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Faux Leather Paper Bag Tie Waist Shorts
Create a sleek and edgy look in these faux leather paper bag shorts. Step out in style in these high-waist shorts with side pockets and a matching self-tie belt. The faux leather material instantly makes dressy shorts the perfect bottoms to pair with your going-out looks for a girls' night out or clubbing. Pair these faux leather shorts with a mesh bodysuit or sparkly corset top for a fierce and sexy look.
Fit & Features
- High-rise paper bag waist
- Tie front belt
- Back zipper, hook and eye closure
- Side pockets
- Form-fitting style
- Faux leather fabric with moderate stretch
- Runs true to size
Style Number/Barcode: 06403-0146
Category Name: Vacation Looks
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Ray Of Sunshine Eyelet Lace Bustier
Look and feel like a ray of sunshine in this eyelet bustier for a flirty day date or weekend plans! The bustier is designed to snatch your figure while the ruffled crop hem adds the prettiest look to your favorite denim shorts.
Fit & Features
- Eyelet lace woven fabric
- Sweetheart neckline
- Adjustable shoulder straps
- Front hook and eye fasteners
- Stretchy smocked back
- Ruffled crop hem
- Runs true to size
Style Number/Barcode: 06003-2767
Category Name: Vacation Looks
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Kacey Formal Halter Pleated Long Dress
Special Occasion
Serve pure bliss in the Kacey formal dress designed for twirling all night at a wedding reception, banquet, or gala! She features an adorable halter neckline with a tie-back closure, an open-back, and a pleated flowy long-length silhouette. The formal dress is composed of a plisse airy fabric with no stretch. Complete your dressy look with a stunning hair accessory for a glam updo and lace-up heels.
Fit & Features
- Sleeveless halter neckline, tie-back closure
- Adhesive bra recommended
- Open-back design
- Hidden back zipper closure
- Pleated, flowy, long-length silhouette
- Plisse airy fabric, no stretch
- Runs true to size
Style Number/Barcode: 05002-3182
Category Name: Vacation Looks
Price: $9.97 $79.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Fawn Over You Marble Print Chiffon Skater Dress
You'll be fawned over when in this marble print chiffon skater dress! From the adjustable spaghetti straps to the flattering square neckline, this dress has got you covered. The stretchy smocked bodice creates a comfortable and perfect fit, while the tie waist belt accentuates your curves. With a playful ruffled tiered short-length hem, this dress is perfect for twirling! Complete the look in wedges for a dressy occasion.
Fit & Features
- Marble print, chiffon lined fabric
- Adjustable spaghetti straps
- Square neckline
- Tie waist belt, ruffled short-length hem
- Runs true to size
Style Number/Barcode: 05101-3081
Category Name: Vacation Looks
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Feeling Pretty Cute Floral Skater Short Dress
Nothing comes as close to cute as this floral skater dress! Perfect for shower celebrations or afternoon teas, this short dress boasts a pretty corset-inspired bodice and a voluminous hem.
Fit & Features
- Floral print, cotton woven fabric, tulle and woven linings
- Square neckline, bust tie
- Wide shoulder straps
- Back zipper and hook-eye closure
- Corset-inspired bodice, pleating
- Skater silhouette, short-length hem, pleated trim
- Runs true to size
Style Number/Barcode: 05101-4037
Category Name: Vacation Looks
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Trendy Style Belted Twill Skort
Show off a trendy style this summer season with this of-the-moment twill skort. It features a mid-rise waist with an adjustable faux leather belt, a hidden side zipper closure, a front skirt overlay with pleated detailing, shorts, and a fitted silhouette. Pair with a graphic tee and booties for a cool vibe.
Fit & Features
- Mid-rise waist, belt loops
- Adjustable faux leather belt, rectangular buckle
- Hidden side zipper closure
- Front skirt overlay, pleating, shorts
- Fitted silhouette
- Smooth twill fabric, no stretch
- Runs true to size
Style Number/Barcode: 06303-0238
Category Name: Vacation Looks
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Adoring Style V-Neck Tie Eyelet Skater Romper
Chanel this adoring and stylish eyelet skater romper for sweet summer looks at BBQs and Fourth of July parties! The V-neckline, spaghetti straps, and surplice bust provide a flattering fit, while the tie-back design adds a touch of sophistication. The skater silhouette and flowy short-length hem create an effortlessly chic look. Complete the look in wedge sandals.
Fit & Features
- Eyelet knit fabric, moderate stretch
- V-neckline
- Spagehtti straps
- Skater silhouette
- Runs true to size
Style Number/Barcode: 06503-1124
Category Name: Vacation Looks
Price: $16.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Summer Glam Espadrille Sequin Fringe Sandals
Slip into these espadrille sequin fringe sandals to glam up to your summer looks! Designed with a braided espadrille material, they feature a round toe, a wide strap across the foot with woven embroidery, shimmering sequins, and trendy fringe trims, and a flat sole. The open back offers effortless on-and-off styling. Pair with your flowy sundresses to create fabulous 'fits for your weekend plans!
Fit & Features
- Espadrille upper material
- Round toe
- Wide strap
- Woven embroidery, sequins, fringe trims
- Open back, flat sole
- On-and-off styling
- Runs true to size
Style Number/Barcode: 07404-1209
Category Name: Vacation Looks
Price: $9.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Kick Up The Style Cowboy Boots
Kick the dust off in these stylish faux leather cowboy boots perfect for music festivals and country bars! They feature a pointed toe, stacked block heel, classic western-inspired stitched designs, and a curved mid-length shaft with pull tabs to easily slide on and off. Complete the look in a fringe cowboy hat.
Fit & Features
- Pointed toe
- Stacked block heel
- Classic western-inspired stitched designs
- Mid-length shaft, pull tabs
- Faux leather material
- Runs true to size
Style Number/Barcode: 07403-1620
Category Name: Vacation Looks
Price: $12.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Take Me Away Crochet Tunic Sweater
Look good on the go in this crochet tunic sweater for your upcoming trip! Designed on sheer crochet fabric, it features long sleeves with chic flare cuffs, a crew neckline, and a sultry open-back design. Finished with a form-hugging fit and short-length hem. Style with sleek hoop earrings.
Fit & Features
- Long sleeves, flare cuffs
- Crew neckline
- Open back design
- Form-hugging
- Short-length
- Sheer crochet fabric
- Runs true to size
Style Number/Barcode: 06005-1828
Category Name: Vacation Looks
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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On Vacay Flower Strap Jelly Sandals
These cute jelly sandals say "I'm on vacay" with the thong strap design and pretty flower accent. The open back offers effortless on-and-off styling.
Fit & Features
- Jelly material
- Open almond-shaped toe
- Thong strap design
- Flower accent
- Open back, on-and-off styling
- Flat sole
- Runs true to size
Style Number/Barcode: 07404-000018
Category Name: Vacation Looks
Price: $6.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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The Vibe Rhinestone Star Clear Shield Sunglasses
Channel that iconic early 2000s vibe with these fabulous clear shield sunglasses! They feature a wide shield design with a flat top, sleek metal and plastic arms with trendy cutout detailing, mini rhinestones and star accents at each side, rubber nose pads, and clear lenses. Style with hoop earrings and a mini handbag.
Fit & Features
- Shield design with flat top
- Metal and plastic arms, cutout detail
- Mini rhinestones, star detail
- Metal nose bridge, rubber nose pads
- Clear lenses
- 100% UV protection
Style Number/Barcode: 07008-1078
Category Name: Vacation Looks
Price: $3.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Drop It Low Rise Bootcut Denim Jeans
Pop, lock, and drop it down in these low-rise denim jeans to give your style a cute throwback vibe! They feature a hip-hugging fit, and a bootcut silhouette, and are composed of premium medium-wash denim with color fading and slight stretch. Complete the look in a flirty crop top and your favorite sneakers!
Fit & Features
- Low-rise waist
- Hip-hugging fit
- Bootcut silhouette
- Front button and hidden zipper closure
- Five-pocket styling, belt loop accents
- Premium medium wash denim, slight stretch, color fading
- Runs true to size
Style Number/Barcode: 06602-0440
Category Name: Vacation Looks
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Western Babe Cow Print Mini Skirt
Make the room say, "Yeehaw" looking like a sassy western babe! Create your perfect party outfit in this cow print mini skirt featuring a high-rise waist, bodycon fit, and a slit accent. The skirt is composed of french terry knit fabric with plenty of stretch. Complete the look with a faux leather bustier and accessories.
Fit & Features
- High-rise waist
- Bodycon silhouette
- Slit accent
- Mini-length hem
- Cow print
- Lined french terry knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06501-0697
Category Name: Vacation Looks
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Outside The Lines Floral Print Maxi Skirt
Style outside the lines and go for a bold chic look in this floral print maxi skirt. Style with the matching top for a complete look.
Shop Matching Top: Outside The Lines Floral Print Crop Top
Fit & Features
- Bold floral print, lined stretchy knit fabric
- High-rise waist
- Flowy maxi-length hem
- Runs true to size
Style Number/Barcode: 06501-1123
Category Name: Vacation Looks
Price: $15.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Throwback Babe Side Slit Mini Skort
Bring on the throwback vibes with this stylish mini skort! It's designed with a high-rise waist, front slit, and a hidden back zipper with a mini skirt overlay and shorts lining. Wear with a crop top to embrace the '90s look.
Fit & Features
- High-rise waist
- Back zipper closure
- Form-hugging, front slit
- Mini skirt overlay
- High-waist shorts
- Smooth woven fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06403-0188
Category Name: Vacation Looks
Price: $6.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Babe Alert Scoop Neck One-Piece Swimsuit
Fit & Features
- Smooth nylon-blend fabric with contrast trim, plenty of stretch
- Scoop neckline, adjustable spaghetti straps
- Low back
- High-cut design, cheeky bottom
- Form-hugging fit
- Runs true to size
- Returns are not accepted without the hygienic liner
Style Number/Barcode: 07105-0871
Category Name: Vacation Looks
Price: $14.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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City Chic Ruffled Midi Dress
Step out like a scene straight out of a rom-com in a midi dress that gives major butterflies! The city-chic midi dress features a sleeveless square neckline, spaghetti straps that lead to a cross-strap design, and a high side slit on the left leg with a romantic ruffled trim. The relaxed fit waist leads to a midi-length A-line silhouette. The dress is composed of a smooth knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with mules.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps, cross-back design
- Strapless bra friendly
- High side slit, ruffled trim
- Relaxed fit waist, A-line silhouette
- Midi-length hem
- Smooth knit fabric
- Form-hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05101-1038
Category Name: Vacation Looks
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sultry Blossom Sweetheart Floral Mesh Mini Dress
Your amount of admirers will blossom when they see you in this sultry floral mesh mini dress! This flirty mini dress features a sweetheart neckline and padded bra cups for a flattering fit. Its adjustable spaghetti straps and ruched seams ensure the perfect bodycon silhouette. Complete the look in block heels.
Fit & Features
- Floral print, mesh fabric, sewn-in knit lining, moderate stretch
- Sweetheart neckline
- Adjustable spaghetti straps, padded bra cups
- Back zipper and hook-eye closure
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5478
Category Name: Vacation Looks
Price: $19.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Cool Meter Mid-Rise Parachute Cargo Pants
These parachute cargo pants have a high rating on the cool girl meter! They feature an elasticized mid-rise waist with side adjustable drawcords, side flap pockets with button closures, a loose-fit silhouette, and an adjustable drawcord hem. Style with a basic crop top for a movie night with friends!
Fit & Features
- Mid-rise elasticized waist, side adjustable drawcords
- Side flap pockets, button closures
- Loose-fit silhouette
- Adjustable drawcord hem
- Lightweight nylon woven fabric, no stretch
- Runs true to size
Style Number/Barcode: 06302-0745
Category Name: Vacation Looks
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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All Angles Metal Trim Square Sunglasses
Sleek and sculpted, these square sunglasses bring instant cool-girl energy. The metal-trimmed arms add just the right hint of shine—your new go-to for blocking shade in style.
Fit & Features
- Sleek square frames
- Tinted lenses
- Metal trim arms
- Rubber nose supports
- 100% UV protection
Style Number/Barcode: 07008-000084
Category Name: Vacation Looks
Price: $10.90
Availability: Out of Stock
Product Badge:- Sale
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High-Rise Destructed Boyfriend Jeans
Give your casually chic outfits an edgy aesthetic with these deconstructed high-rise jeans. These boyfriend-fit medium-wash denim jeans have the perfect amount of ripped detailing at the knees with a straight-leg silhouette for an absolutely on-trend look. Pair these high-waist ripped jeans with a cute crop top and chunky sneakers for day or a sparkly bustier with strappy heels for a sexy night look.
Fit & Features
- High-rise waist
- Boyfriend style leg
- Distressed detailing, slits at the knees
- Multi button-down front closure
- Five-pocket and belt loop design
- Medium wash denim fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06602-0184
Category Name: Vacation Looks
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance