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 Looks
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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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Stun The Scene V-Neck Lace Mesh Crop Top
Your attraction will be undeniable in this scenic print mesh crop top perfect for adding a romantic look! It features a flirty V-neckline adorned with delicate lace trim and ribbon, spaghetti straps, a babydoll silhouette that flatters, and a flowy cropped hem. Complete the look in a denim skirt and sandals for any casual plans!
Fit & Features
- Scenic print, sheer mesh fabric, moderate stretch
- Spaghetti straps
- V-neckline, lace trim and ribbon
- Babydoll silhouette
- Runs true to size
Style Number/Barcode: 06001-5391
Category Name: Vacation Looks
Price: $6.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Miami Nights Sleeveless Tropical Slit Maxi Dress
Turn up the heat in Miami in this tropical maxi dress on vacay! The square neckline and spaghetti straps accentuate your curves in a form-hugging fit while the high side slit adds a touch of sassy sophistication. Let the tropical print and maxi-length hem transport you to a paradise getaway! Complete the look in sandals.
Fit & Features
- Tropical print, knit fabric, stretchy short lining
- Spaghetti straps
- High side slit
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 05102-5624
Category Name: Vacation Looks
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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In My Element V-Neck Bow Ruffled Floral Romper
Time to show your playful side in this sleeveless ditsy floral romper for spring-to-summer fun! With a surplice V-neckline, adjustable spaghetti straps, and an open crisscross back, you'll turn heads. The front bow tie waist and ruffled short-length hem add a touch of fun to the ditsy floral print woven fabric. Complete the look in stiletto mules and earrings!
Fit & Features
- Ditsy floral print woven fabric, partial knit lining, minimal stretch
- Surplice V-neckline
- Adjustable spaghetti straps, open back, cross-back strap design
- Back zipper with hook and eye closure
- High waist seam, tie-front bow
- Ruffled short-length hem
- Runs true to size
Style Number/Barcode: 06403-0379
Category Name: Vacation Looks
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Beachy Perfection Strappy Straw Block Heels
These straw heels are the definition of beachy perfection! They feature a square toe with dual straps, an adjustable ankle strap with buckle closure to secure the style, and a trendy circular block heel. Complete the look with a cute tote bag for a beach trip!
Fit & Features
- 2.5" Circular block heel
- Square toe
- Dual straps
- Adjustable ankle strap with buckle closure
- Straw material
- Faux leather padded insole
- Runs true to size
Style Number/Barcode: 07401-4863
Category Name: Vacation Looks
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Stylish In Stripes Strapless Wide Leg Knit Jumpsuit
Spend your days looking stylish in this striped jumpsuit perfect for layering over your swimsuit or wearing on its own. The jumpsuit features a strapless neckline and an adjustable drawstring waist that cinches, leading to the flattering wide-leg silhouette. Complete the look with chic sunglasses.
Fit & Features
- Striped pattern, knit fabric, moderate stretch
- Strapless neckline
- Adjustable drawstring waist
- Wide-leg silhouette
- Runs true to size
Style Number/Barcode: 06502-2539
Category Name: Vacation Looks
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Oasis Babe Floral Wrap Tie Sarong
Perfect for poolside lounging or beachfront dining, this sarong adds instant babe status to your vacation wardrobe. This mesh sarong can be styled as a swimsuit cover-up or a stylish skirt with its adjustable tie design, with a vibrant floral print that captures tropical vibes.
Fit & Features
- Mesh fabric, floral print, stretchy
- Wrap tie adjustable waist
- Sheer design
Style Number/Barcode: 07105-000015
Category Name: Vacation Looks
Price: $9.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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In For The Frills Mid-Rise Eyelet Ruffle Shorts
Romp around in these adorable eyelet ruffle shorts for weekend brunch or a festival! Designed with a smocked mid-rise waist and flirty lace trim.
Fit & Features
- Eyelet lace chiffon fabric
- Stretchy knit shorts lining
- Smocked mid-rise waist
- Ruffled silhouette
- Runs true to size
Style Number/Barcode: 06403-1110
Category Name: Vacation Looks
Price: $15.97 $34.90
On Sale: Yes
Availability: In Stock
Available Color: IVORY
Available Size: L
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Sunny Dreams High-Rise Distressed Denim Shorts
Keep it cute and casual all season in these denim shorts from fun at the beach to weekend hangs! They feature a flattering high-rise waist, trendy distressed accents along the form-hugging silhouette, and a raw cut-off hem. Complete the look in a basic tee and sneakers!
Fit & Features
- Denim material with stretch
- High-rise waist
- Distressed accents
- Form-hugging
- Front button and hidden zipper closure
- Five-pocket styling
- Runs true to size
Style Number/Barcode: 06603-0397
Category Name: Vacation Looks
Price: $6.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Poolside Flirt String Bikini Top
Sit flirty and pretty in this eyelet string bikini top at a pool party or on vacation! Pair with the matching bikini bottoms.
Fit & Features
- Eyelet lined fabric
- Triangle cups
- Dual string spaghetti back ties
- Runs true to size
Shop The Matching Bikini Bottoms: Poolside Flirt Eyelet String Bikini Bottoms
Style Number/Barcode: 07104-0719
Category Name: Vacation Looks
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Serve Attitude Cat Eye Sunglasses
These aren’t just sunglasses—they’re your armor of IDGAF. With a sleek cat eye shape that oozes retro cool and mystery, these frames instantly upgrade your fit and your mood.
Fit & Features
- Cat eye frames
- Tinted lenses
- 100% UV protection
Style Number/Barcode: 07008-000065
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Perfect Striped Halter V-Neck Mini Dress
This striped mini dress will easily become your perfect favorite piece this season! The halter V-neckline and open back highlight your alluring figure, while the bodycon fit and mini-length hem flatters your curves on the striped mesh-lined fabric. Complete the look with sunglasses and sandals for a day out or on vacation!
Fit & Features
- Striped print, mesh fabric, soft stretchy knit lining
- Halter V-neckline
- Open back
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5811
Category Name: Vacation Looks
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sunny Chic High Slit Crochet Maxi Skirt
Create a sunny chic 'fit with the cutest crochet maxi skirt! Designed with a breezy sheer crochet knit fabric with a built-in panty lining, this skirt was made for summer getaways. It features a high-rise banded waist with a front adjustable drawstring for a customized fit, a high-cut back slit, and a slim-fit silhouette. Complete your look with the matching crop top and a pair of slip-on sandals!
Shop Matching Top: Sunny Chic Halter Ruched Crochet Crop Top
Fit & Features
- Sheer crochet knit fabric, moderate stretch
- Built-in knit panty lining
- High-rise elastic banded waist
- Front adjustable drawstring
- High back slit
- Slim-fit silhouette
- Runs true to size
Style Number/Barcode: 06501-0917
Category Name: Vacation Looks
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Vacay Vibes High Slit Tropical Knit Maxi Dress
Give off effortless vacay vibes in this high slit tropical knit maxi dress. The tropical palm leaf print on the lightweight knit fabric will have you looking like you're ready for a getaway, even if you're just grabbing drinks at a local happy hour! The dress is shaped with a sleeveless V-neckline and spaghetti straps, and features a high-cut side slit to showcase some leg on the form-hugging mid-length silhouette. Style with gold hoops and strappy wedges!
Fit & Features
- Stretchy knit fabric with a bust lining
- Tropical print
- Sleeveless V-neckline
- Spaghetti straps
- High side slit
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 05102-5537
Category Name: Vacation Looks
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Covetable Charm V-Neck Ruffled Maxi Dress
You'll covet the charm of this sleeveless maxi dress all season! With a flattering V-neckline and adjustable spaghetti straps, this dress will hug you in all the right places. The crisscross and smocked back add a trendy touch, while the flowy silhouette and ruffled long-length hem offer a breezy style. Complete the look in sandals.
Fit & Features
- Woven fabric, bust lining, no stretch
- Adjustable spaghetti straps
- Crisscross and smocked back
- Flowy silhouette
- Ruffled hem
- Runs true to size
Style Number/Barcode: 05102-5546
Category Name: Vacation Looks
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Think Sunshine Long Sleeve Cutout Crochet Mini Dress
Get in the summer vibe with this crochet mini dress perfect for pool parties or vacation! Featuring sheer flared long sleeves for a trendy touch, a sexy V-neckline, and a cutout waist and back for a daring look. The hoop insert adds a unique twist and the tie-back design creates a flattering look along the bodycon silhouette. Complete the look with sunglasses and sandals!
Fit & Features
- Crochet fabric, sewn-in knit lining, slight stretch
- Sheer flared long sleeves
- V-neckline
- Hoop insert, cutout waist and back
- Tie-back design
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5732
Category Name: Vacation Looks
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Perfect Company Sleeveless Button-Up Vest
Never worry about looking stylish with this sleeveless vest in your lineup! Designed from a linen-blend woven fabric, this vest offers a classic and trendy vibe with a collar neckline, button-up front closures, faux pockets, and a cropped hem. Complete the look in denim shorts.
Fit & Features
- Linen-blend woven fabric, no stretch
- Collar neckline
- Button-up front closures
- Buttoned chest pockets
- Cropped hem
- Runs true to size
Style Number/Barcode: 06204-1785
Category Name: Vacation Looks
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Meant To Be Surplice V-Neck Strappy Chiffon Romper
This chiffon romper was meant to be adored by everyone at showers or celebrations! The surplice V-neckline and adjustable spaghetti straps provide a flattering fit, while the crisscross open back adds a touch of playful charm. The tie waist cinches in at the perfect spot, and the layered ruffled short-length hem adds a flirty and feminine touch. Complete the look in wedge sandals.
Fit & Features
- Textured chiffon fabric, chiffon woven lining
- Surplice V-Neckline, adjustable spaghetti straps
- Criss-cross open back, zipper and hook-eye closure
- Layered ruffled short-length hem
- Runs true to size
Style Number/Barcode: 06403-0418
Category Name: Vacation Looks
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Chic Daydream Butterfly Chain Belt
Soft girl energy? Activated. This butterfly chain belt flutters right into your faves with dreamy layered charms and delicate movement—perfect for cinching your waist with a little fairycore flair.
Fit & Features
- Chain-link design
- Small and large butterfly charm accents
- Adjustable fit with lobster clasp closure
Style Number/Barcode: 07301-000144
Category Name: Vacation Looks
Price: $3.97 $14.90
On Sale: Yes
Availability: In Stock
Available Color: GOLD
Available Size: NS
Product Badge:- Sale
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Pretty In Paradise One-Shoulder Tropical Maxi Dress
You'll be looking so pretty as you stroll the beach in paradise in this tropical maxi dress! The smooth stretchy knit fabric showcases a bold tropical print perfect for an island vacay. The long dress is shaped with a sleeveless asymmetric one-shoulder neckline with a single spaghetti strap. The sultry ruched cutout at the waist features an adjustable drawstring for a customized look. Reveal some leg with the sexy high-cut side slit on the maxi-length silhouette. Style this slim-fit dress with espadrille wedges.
Fit & Features
- Stretchy knit fabric, knit lining at the bust
- Tropical print
- Asymmetric one-shoulder neckline, spaghetti strap
- Ruched side cutout, adjustable drawstring
- High side slit
- Slim-fit silhouette
- Runs true to size
Style Number/Barcode: 05102-5542
Category Name: Vacation Looks
Price: $9.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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On The Prowl Strapless Zebra Crop Top
On the prowl and ready to unleash fierceness in this zebra print crop top! It features a strapless neckline, a tie-back design, and a fitted crop hem that flaunts your figure. Complete the look with the matching skirt.
Shop Matching Skirt: On The Prowl High Rise Zebra Maxi Skirt
Fit & Features
- Zebra print, woven fabric, bust knit lining
- Strapless neckline
- Tie-back design
- Fitted crop hem
- Runs true to size
Style Number/Barcode: 06003-2507
Category Name: Vacation Looks
Price: $6.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Never A Dull Moment Strapless Cutout Maxi Dress
Bring a stunning look in this strapless maxi dress for your look-back-it moment! The strapless neckline and cutout bust add a touch of allure, while the strappy back and form-hugging fit emphasize your figure. With a center-back slit, you'll be able to move in style. Complete the look with earrings and a clutch!
Fit & Features
- Rib knit fabric, sewn-in knit lining, moderate stretch
- Strapless neckline
- Cutout bust, strappy back
- Form-hugging fit
- Center back slit
- Runs true to size
Style Number/Barcode: 05102-5766
Category Name: Vacation Looks
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Fiji Feeling Sleeveless Lace-Up Tropical Maxi Dress
Escape to the island or look like you did in this tropical maxi dress for an effortless summer style! With a flattering V-neckline and delicate spaghetti straps, this dress will keep you stylish all day long. The lace-up back adds a touch of playful detail, while the A-line silhouette and maxi-length hem create a flowy and romantic look.
Fit & Features
- Palm leaf tropical and border print, woven fabric with lining, no stretch
- V-neckline
- Spaghetti straps
- Lace-up back
- A-line maxi silhouette
- Runs true to size
Style Number/Barcode: 05102-5864
Category Name: Vacation Looks
Price: $11.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweet Sun Floral Bikini Bottoms
Enjoy the sweet sunshine at the pool or beach in these floral bikini bottoms! Pair with the matching bikini top.
Fit & Features
- Floral print, knit lined fabric
- Low-rise waist
- Ruffle trim
- Cheeky bottom
- Returns are not accepted without the hygienic liner
- Runs true to size
Shop The Matching Bikini Top: Sweet Sun Floral Tie-Front Bikini Top
Style Number/Barcode: 07105-0867
Category Name: Vacation Looks
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Vacation Queen High-Rise Slit Tropical Maxi Skirt
Unleash your inner vacation queen with this tropical maxi skirt! Made from stretchy knit fabric, this skirt is perfect for any tropical adventure with its eye-catching palm print. Its high-rise waist and flowy silhouette will flatter your figure, while the high front slit adds a touch of sass. Complete the look with sandals.
Fit & Features
- Tropical palm print, stretchy knit fabric, bikini brief lining
- High rise waist
- High front slit
- Flowy silhouette
- Runs true to size
Style Number/Barcode: 06501-0967
Category Name: Vacation Looks
Price: $16.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free