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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Easy Breezy Straw Clutch Bag
One bag, endless ways to wear it. This straw foldover clutch comes with a detachable wrist strap and crossbody strap, making it the ultimate grab-and-go sunny day accessory!
Fit & Features
- Front foldover flap with snap-button closure
- Detachable faux leather wrist strap
- Detachable faux leather crossbody strap
- Top zipper closure
- Spacious lined interior
- Straw material
Style Number/Barcode: 07203-000118
Category Name: Vacation Looks
Price: $6.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Glamour Steps Rhinestone Strappy Flat Sandals
Add glamour to your steps in these faux leather flat sandals showcasing a sparkling rhinestone embellished trim, round toe, and rhinestone-embellished strappy design with an adjustable ankle strap with buckle closure. Complete the look in a casual bodycon dress for a day out and about!
Fit & Features
- Flat sole
- Faux leather material
- Round toe
- Rhinestone trim
- Rhinestone embellished strappy design
- Adjustable ankle strap, buckle closure
- Luxe fit cushioned insole
- Runs true to size
Style Number/Barcode: 07404-1158
Category Name: Vacation Looks
Price: $9.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Too Cool Contrast Trim Faux Leather Sneakers
These faux leather sneakers are too cool for school! Kick back in these exclusive shoes featuring a round toe and lace-up placket for a perfect fit. A cool contrast trim for added style and a comfortable footbed and rubber insole. Complete the look with a zip-up hoodie for casual plans.
Fit & Features
- Round toe
- Lace-up placket
- Contrast trim
- Comfortable footbed
- Rubber insole
- Runs true to size
Style Number/Barcode: 07407-0225
Category Name: Vacation Looks
Price: $28.90
Availability: Out of Stock
Product Badge:- Ships Free
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Chic Fit Strapless Faux Wrap-Front Romper
This strapless romper will give you a chic fit with its faux wrap-front design and form-hugging silhouette. Style for happy hour with strappy mules.
Fit & Features
- Smooth woven fabric, partial knit lining, moderate stretch
- Strapless straight neckline, no-slip strip, dart seams
- Back zipper with hook-eye closure
- High waist seam
- Faux wrap-front mini-length overlay, short slit, fitted shorts
- Romper in size small is 22" top hem to bottom hem with a 12" front rise and a 2" inseam
- Runs true to size
Style Number/Barcode: 06403-1105
Category Name: Vacation Looks
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
- Smooth woven fabric, partial knit lining, moderate stretch
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Casual Scene Crew Neck Midi Dress
Your next casual plans call for this t-shirt midi dress for grabbing coffee or running errands in style! It features a classic crew neck, short sleeves, a cutout waist with a knot accent, a bodycon silhouette, and a flirty front slit on smooth cotton knit fabric. Complete the look in cute strappy sandals.
Fit & Features
- Crew neck, short sleeves
- Cutout waist, knot accent
- Bodycon silhouette
- Front slit, midi-length hem
- Smooth cotton knit fabric
- Moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5765
Category Name: Vacation Looks
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweet Escape Lace-Up Tropical Midi Dress
Have the sweetest look in this tropical midi dress for your next vacay escape! With a flattering square neckline, delicate spaghetti straps, and a lace-up back, this bodycon dress will hug your curves down to the high-cut asymmetrical midi-length hem. Complete the look in espadrille wedges.
Fit & Features
- Tropical print, lined knit fabric, plenty of stretch
- Square neckline
- Spaghetti straps
- Lace-up back
- Asymmetric high-cut hem
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5564
Category Name: Vacation Looks
Price: $19.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Western Showdown Etched Concho Belt
Saddle up with this playful etched concho belt, featuring an adjustable lobster clasp closure. Wrangle up some western vibes and complete the look in denim shorts for a festival or concert.
Fit & Features
- Etched concho belt
- Adjustable lobster clasp closure
Style Number/Barcode: 07301-1113
Category Name: Vacation Looks
Price: $14.90
Availability: In Stock
Available Color: GOLD, SILVER
Available Size: NS
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Luxe Flair Woven Loop Satin Scarf
Add a luxe flair to your spring and summer 'fits with this woven loop satin scarf! Designed with a silky satin material with a chic woven loop pattern, this sleek scarf offers multiple styling options. Tie it around your neck for a fab accent, as a headwrap, or a trendy hair tie! Pair with chunky gold hoop earrings.
Fit & Features
- Non-stretch satin material
- Woven loop pattern
Style Number/Barcode: 07305-0491
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Fresh Pick Flower Detail Sunglasses
Shade, but make it sweet. These sleek frame sunglasses get a playful twist with flower side details—your go-to pair for adding instant charm to sunny days.
Fit & Features
- Sleek metal frame design
- Flower detail side accents on the arms
- Tinted lenses
- Rubber nose supports
- 100% UV protection
Style Number/Barcode: 07008-000100
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sunny Vibes High Slit Woven Midi Skirt
This airy woven midi skirt will bring the sunny vibes to your weekend plans! Designed with a lightweight woven fabric with a mini-length lining, it features a high waist with the cutest tie detail, a high-cut side slit to showcase some leg, and a flowy slim-fit silhouette. Style with the matching crop top for a fabulous 'fit!
Shop Matching Orange Top: Sunny Vibes Bow Back Woven Crop Top
Fit & Features
- Woven fabric with mini-length knit lining, minimal stretch
- High-rise elasticized waist
- Tie detail
- High side slit
- Flowy slim-fit silhouette
- Runs true to size
Style Number/Barcode: 06401-0651
Category Name: Vacation Looks
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Chic Breeze Chain Printed Satin Scarf
Add a luxe flair to your spring and summer 'fits with this woven chain-printed satin scarf! Designed with a silky satin material with a chic woven chain pattern, this sleek scarf offers multiple styling options. Tie it around your neck for a fab accent, as a headwrap, or a trendy hair tie! Pair with high-rise denim shorts.
Fit & Features
- Satin chain printed woven scarf
- Multiple styling options
Style Number/Barcode: 07305-0500
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Chasing The Sun Banner Woven Satin Scarf
Chase this sun banner silky woven scarf for the perfect look for your next sweet escape! Designed with a silky satin material with a chic sun banner pattern, this sleek scarf offers multiple styling options. Tie it around your neck for a fab accent, as a headwrap, or a trendy hair tie! Pair with a sultry jumpsuit.
Fit & Features
- Sun banner print
- Woven satin fabric
- Multiple styling options
Style Number/Barcode: 07305-0499
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Free Riders Colored Stone Chain Belt
Accessorize your ride with this statement western chain belt featuring unique colored stones, oval-shaped charms, and an adjustable lobster clasp closure to secure the style. Complete the look in a fitted mini dress.
Fit & Features
- Colored stones
- Oval-shaped charms
- Adjustable lobster clasp closure
Style Number/Barcode: 07301-1146
Category Name: Vacation Looks
Price: $6.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Boardwalk Crop Denim Jacket
Stroll the boardwalk before your sunset dinner in this streetwear-inspired crop denim jacket featuring long sleeves with buttoned cuffs, a collared neckline, four-button front closure, flap pockets, distressed accents, and a pull tab button closure along the hem. Complete the look in breezy wide-leg pants and a bodysuit.
Fit & Features
- Non-stretch denim fabric
- Long sleeves, buttoned-cuffs, collared neckline
- Four-button front closure
- Flap pockets, buttons
- Distressed accents
- Pull tab button closure along crop hem
- Runs true to size
Style Number/Barcode: 06203-0540
Category Name: Vacation Looks
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Double Trouble Snake Chain Lariat Necklace Set
Two chains, one goal—steal the spotlight. This snake chain lariat necklace set is your new go-to for stacking drama and drip, whether you’re out for dinner or just feelin’ yourself in selfies.
Fit & Features
- Two-pack necklace set
- Short snake chain
- Longer snake chain, triangle-shaped center accent, long lariat design
- Back lobster clasp closures with extenders
Style Number/Barcode: 07002-000026
Category Name: Vacation Looks
Price: $4.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Bold Simplicity Bodycon Maxi Skirt
No frills, no fuss—just pure silhouette. The smooth look, bodycon fit, and maxi hem give you an effortlessly pulled-together look that’s timeless yet modern. Pair with the matching top.
Shop The Matching Top: Bold Simplicity Crop Tank Top
Fit & Features
- Double-lined slinky knit stretchy fabric
- Mid-rise waist
- Side ruched seams
- Bodycon silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 06501-000076
Category Name: Vacation Looks
Price: $13.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Cubic Zirconia Studs Set
Glam up your look with this cubic zirconia stud earrings set. This pack of six varying-sized studs gives you the option of how much bling you want to rock for the day. Perfect to dress up an everyday outfit to go run errands. Pair with a chic bodysuit and distressed denim and you'll be all ready to go!
Fit & Features
- Cubic zirconia
- Post-back closures, rubber stoppers
- Set of six studs
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-3731
Category Name: Vacation Looks
Price: $12.90
Availability: Out of Stock
Product Badge:- Ships Free
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When Life Gives You Lemons Tote Bag
Carry summer vibes everywhere with this canvas tote bag! This eye-catching canvas tote features a vibrant lemon print that adds a refreshing pop to any outfit while providing plenty of space for your must-haves.
Fit & Features
- Top handles
- Lemon print design
- Spacious interior
- Canvas material
Style Number/Barcode: 07203-000026
Category Name: Vacation Looks
Price: $4.97 $9.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Ardell Demi Wispies Lashes 5 Pack
Glam up your eyes with these gorgeous lashes. The Ardell Demi Wispies lashes offer a natural, long feathered and glamorous look, are easy to apply, and are even reusable! Perfect for your next sexy night out outfit like a sultry crop top and mini skirt. The lashes work best for large and deep-set eyes. Don't forget to pick up the eyelash glue!
Fit & Features
- Long, feathered natural look
- Reusable
- Includes 5 sets of eyelashes
- Eyelash glue sold separately
Style Number/Barcode: 07307-0372
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Beautiful Bliss Floral Sequin Mesh Babydoll Dress
Get swept up in the beauty of this babydoll dress perfect for brides-to-be, wedding showers, and dressy soirees! The sheer 3/4 length puff sleeves and square neckline add a touch of romance, while the babydoll silhouette and short hem create a playful and flirty look. The floral embroidery and sequins on the sheer mesh overlay add a touch of whimsy to this stunning dress. Complete the look with a chic ring set and heels!
Fit & Features
- Sheer mesh overlay line with woven fabric
- Floral embroidery, sequin embellishments
- Back zipper and hook-eye closure
- Babydoll silhouette
- Runs true to size
Style Number/Barcode: 05101-3357
Category Name: Vacation Looks
Price: $26.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Stunning Sparkle Large Hoop Earrings
Give off a stunning sparkle when these hoops catch the light! These hoop earrings feature beautiful crystal-like details to top off all your looks with a bit of bling. Topped with post-back closures for easy wear. Style these sleek hoops with a chic bodysuit and high waist jeans for an effortlessly put-together look.
Fit & Features
- Large hoop design
- Cyrstal-like details
- Post-back closure
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-0105
Category Name: Vacation Looks
Price: $10.90
Availability: Out of Stock
Product Badge:- Ships Free
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Here To Slay One-Shoulder Cutout Knit Crop Top
This iconic crop top was here to stay and slay your 'fits! Made with a stretchy ribbed knit fabric, it features an asymmetric one-shoulder neckline with a tank strap, a trendy twist-front design and sultry center bust cutout, and a cropped hem with a form-hugging fit for a snatched look. Style with high-rise jeans and sneakers for a cute and casual vibe!
Fit & Features
- Stretchy ribbed knit fabric
- Asymmetric one-shoulder neckline, tank strap
- Twist-front design
- Bust cutout
- Cropped
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06002-1950
Category Name: Vacation Looks
Price: $9.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Right Impression V-Neck Floral Ruffle Skater Dress
A cutie like you will always make the right impression in this floral skater dress on dates or at brunch! Featuring sheer peasant long sleeves and a flattering V-neckline, this skater silhouette is completed with a ruffled short-length hem. The V-cut back with a spaghetti strap tie adds a touch of allure. Style this floral skater dress with block heels.
Fit & Features
- Floral print, chiffon fabric with woven lining, no stretch
- V-neckline, V-cut back with spaghetti strap tie
- Skater silhouette
- Ruffled short-length hem
- Runs true to size
Style Number/Barcode: 05101-2894
Category Name: Vacation Looks
Price: $6.97 $56.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Artful Drama Floral Open Back Maxi Dress
Serve artful drama in this halter maxi dress featuring a draped cowl neckline, sultry open back, and a watercolor-inspired floral print. Made for cocktail receptions, weddings, and statement entrances into parties.
Fit & Features
- Watercolor floral print, mesh-lined fabric, stretchy
- Cowl halter neckline, tie closure
- Open back with tie closure
- Curve-hugging silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-000690
Category Name: Vacation Looks
Price: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale