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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Tropical Cutie Halter Cutout Wide-Leg Jumpsuit
This tropical halter jumpsuit will transport you to a beautiful paradise! The sleeveless plunging halter neckline and cutout bodice are both trendy and flattering, while the wide-leg silhouette adds a touch of style to the stretchy smooth knit fabric. Complete the look in strappy sandals.
Fit & Features
- Tropical palm leaf print
- Smooth knit fabric, moderate stretch
- Plunging halter neckline with tie closure, partial open back
- Cut out bodice
- Hip-hugging fit
- Wide-leg silhouette
- Runs true to size
Style Number/Barcode: 06502-2493
Category Name: Vacation Looks
Price: $17.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Destination Paradise Tropical Slit Maxi Dress
Make a statement in this tropical maxi dress on your next visit to paradise! This stunning strapless maxi dress features an alluring side cutout and flirty side slit that creates movement with every step.
Fit & Features
- Tropical print, smooth knit stretchy fabric
- Strapless neckline
- Side cutout with adjustable drawstring
- High side slit
- Form-hugging fit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000138
Category Name: Vacation Looks
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Chic Muse Watercolor Wrap-Slit Midi Skirt
Showcase your iconic style like the chic muse you are in this printed wrap-slit midi skirt! Crafted from a breezy woven fabric with a stretchy knit lining, it is detailed with a gorgeous watercolor print for a mesmerizing look. This skirt features delicate pleating, leading to the wrap-slit front design and a midi-length hem. Style with the matching crop top and espadrille wedges for a sunset dinner!
Shop Matching Top: Chic Muse Watercolor Tie-Front Crop Top
Fit & Features
- Watercolor print
- Woven fabric, stretchy knit lining
- High-rise pleated waist
- Back zipper and hook-eye closure
- Front wrap-slit design
- Midi-length
- Runs true to size
Style Number/Barcode: 06301-0186
Category Name: Vacation Looks
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Found Love Corset Rhinestone Lace Skater Dress
Celebrate your romantic era in this strapless skater dress designed with a corset bodice that snatches your figure and rhinestone embellishments for a glam allure!
Fit & Features
- Lace-lined fabric, rhinestone embellishments
- Strapless sweetheart neckline, padded bra cups, non-slip grip lining
- Corset bodice, flexible boning
- Back zipper and hook-eye closure
- Skater silhouette
- Short-length hem
- Runs true to size
Style Number/Barcode: 05101-3935
Category Name: Vacation Looks
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Soak Up The Rays O-Ring Bikini Bottoms
Get ready to soak up the rays in these chic O-ring bikini bottoms, which have a flattering low-rise waist and flirty, cheeky bottom coverage! Pair with the matching bikini top.
Fit & Features
- Lined knit fabric
- Low-rise waist, spaghetti strap side ties
- O-ring insets
- Cheeky bottom coverage
- Runs true to size
- Returns are not accepted without the hygienic liner
Shop The Matching Bikini Top: Soak Up The Rays O-Ring Bikini Top
Style Number/Barcode: 07105-0869
Category Name: Vacation Looks
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Too Cute to Care Babydoll Mini Dress
Low effort, high reward kind of vibe. This babydoll mini dress features a strappy cutout back and hidden pockets—aka your new throw-on-and-slay essential.
Fit & Features
- Poplin woven fabric
- Square neckline
- Spaghetti straps
- Spaghetti strap tie-back and cutout accent
- Hidden side pockets
- Babydoll silhouette, mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000092
Category Name: Vacation Looks
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Knock Knock Statement Earrings
Bold enough to stand out, chic enough to wear on repeat. These geometric door knocker earrings bring vintage vibes with a modern twist—and they're ready to elevate everything.
Fit & Features
- High-shine metal finish
- Chunky geometric hoop design
- Door knocker-inspired silhouette
- Post back closure
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-000039
Category Name: Vacation Looks
Price: $9.90
Availability: Out of Stock
Product Badge:- Ships Free
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Getaway Bound Lace-Up Print A-Line Dress
With an Italian-inspired print, this A-line dress is perfect for packing with you! This dress is designed in a flattering A-line mini silhouette with a stylish lace-up front and a chic cutout back that turns heads.
Fit & Features
- Multi-printed, woven fabric, woven lining
- V-neckline with lace-up bust
- Adjustable spaghetti straps
- Cutout back
- A-line silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000150
Category Name: Vacation Looks
Price: $10.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Wild Side Leopard Halter Crop Top
Serving up fierce with a side of flirty, this halter crop top is pure attitude. The hoop inserts bring the drama while the fit keeps it effortlessly cool for nights out or rooftop hangs.
Shop The Matching Bottoms: Wild Side Leopard Wide-Leg Pants
Fit & Features
- Soft stretch knit fabric with leopard print
- Halter neckline with hoop insert details, tie closure
- Cropped silhouette with open back and tie closure
- Crop hem
- Runs true to size
Style Number/Barcode: 06001-000265
Category Name: Vacation Looks
Price: $29.90
Availability: In Stock
Available Color: MULTI
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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Everyday Allure Plunging Linen Corset Top
Show off an everyday allure in this sultry plunging linen corset top! Designed with a lightweight linen-blend fabric, it features a sleeveless sweetheart plunging neckline, pleating at the bust, an angled underwire and flexible boning to provide structure, and thin tank shoulder straps. The back hook and eye closures offer a secure fit, and the fitted, angled, cropped hem gives that snatched silhouette. Style with distressed jeans and booties!
Fit & Features
- Linen-blend woven fabric lined with knit, slight stretch
- Sleeveless plunging sweetheart neckline
- Pleated bust, angled underwire, flexible boning
- Thin tank straps
- Back hook and eye closures
- Fitted, angled, cropped hem
- Runs true to size
Style Number/Barcode: 06003-2307
Category Name: Vacation Looks
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Bold And Beautiful Rosette Halter Cutout Maxi Dress
Step out like a bold beauty in this printed maxi dress for brunch, shower celebrations, or parties! This stunning maxi features an elegant halter neckline adorned with rosette detail, flirty cutouts that flatter your silhouette, and a flowing skirt that moves gracefully with every step.
Fit & Features
- Abstract print, woven fabric
- Halter neckline with rosette detail, bust knit lining
- Side cutout accents
- Flowy ruffled maxi-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000054
Category Name: Vacation Looks
Price: $9.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Subtle Charm V-Neck Ruffled Floral Skater Dress
Embrace your inner charm in this floral skater dress at showers or birthdays! The flattering V-neckline and adjustable spaghetti straps provide a perfect fit, while the tiered ruffled skater silhouette adds a touch of feminine flair. With its tie-back design, short-length hem and beautiful floral print, this dress will make you feel effortlessly stylish. Complete the look in mules and earrings!
Fit & Features
- Ditsy floral print
- Chiffon fabric lined with stretchy knit
- Adjustable spaghetti straps
- Tie-back design
- Tiered ruffled skater silhouette
- Runs true to size
Style Number/Barcode: 05101-3022
Category Name: Vacation Looks
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Playful Mood Strapless Ruffled Skater Dress
Frolicking is expected in this playful ruffled skater dress at brunch, shower celebrations, or graduation parties!
Fit & Features
- Chiffon lined fabric
- Strapless sweetheart neckline
- Stretchy smocked bodice
- Ruffled skater silhouette
- Short-length hem
- Runs true to size
Style Number/Barcode: 05101-3999
Category Name: Vacation Looks
Price: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Gorgeous Perfection Halter Floral Chiffon Crop Top
Be gorgeous and perfect all season in this floral chiffon crop top at formal soirees! Made with floral and leaf print chiffon fabric, this top is a must-have for any fashion-forward girlie. Its sleeveless halter neckline and cropped hem create a flattering fit. Complete the look with the matching skirt.
Shop The Matching Skirt: Gorgeous Perfection Ruffled Floral Chiffon Maxi Skirt
Fit & Features
- Floral and leaf print, chiffon fabric lined with stretchy knit
- Halter neckline
- Back zipper hook-eye closure
- Cropped length
- Runs true to size
Style Number/Barcode: 06003-2505
Category Name: Vacation Looks
Price: $6.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Breezy As Can Be Strapless Ruffled Midi Dress
This midi dress will be your go-to choice from shower celebrations to sunset dinners. Cascading ruffles create a feminine silhouette that flows with your movements, while the midi hem lets you show off your shoes.
Fit & Features
- Gauze woven fabric, woven lining
- Strapless smocked stretchy bodice
- Ruffled cascading silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-000027
Category Name: Vacation Looks
Price: $15.97 $69.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Pretty Picture Striped Midi Dress
With an ice cream in hand and strappy sandals on, this striped midi dress will have you looking pretty everywhere you go! Featuring a flattering square neck and curve-hugging fit, this dress accentuates your figure down to the midi hem.
Fit & Features
- Striped print, stretchy knit fabric, sewn-in knit lining
- Square neckline
- Wide shoulder straps
- Curve-hugging fit
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-5860
Category Name: Vacation Looks
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Gone Coastal Snake Triangle Bikini Top
If you're heading on vacay or the beach, this snake triangle bikini top will keep you fiercely stylish on and off the shore! Pair with the matching bikini bottoms.
Fit & Features
- Snake print, lined fabric
- Triangle cups, removable padded bra cups
- Adjustable spaghetti straps
- Back spaghetti strap tie
- Runs true to size
Shop The Matching Bikini Bottoms: Gone Coastal Snake Side Tie Bikini Bottoms
Style Number/Barcode: 07104-0729
Category Name: Vacation Looks
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Boho Era Multi-Beaded Bracelet Set
Effortless and made for your boho era. This four-pack bracelet set levels up any look with a mix of bold beads and breezy vibes—just stack and go, babe.
Fit & Features
- Four-pack bracelet set
- Multi-beaded designs with smooth and faceted textures
- Layered look with mixed bead shapes and finishes
- Stretchy fit
Style Number/Barcode: 07003-000027
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Moment Of Beauty Lace Up Floral Maxi Dress
Have your moment of beauty during soiree hour in this floral maxi dress perfect for showers or garden parties! The vibrant floral print adds an extra touch of fun to this maxi length dress. Featuring a playful lace up back, adjustable spaghetti straps, and a high front slit, this dress will have you looking effortlessly chic! Complete the look with earrings and block heels.
Fit & Features
- Floral print, chiffon fabric lined with stretchy knit
- Adjustable spaghetti straps
- Lace up back
- V-neckline, padded bra cups
- High front slit
- Maxi silhouette
- Runs true to size
Style Number/Barcode: 05101-3047
Category Name: Vacation Looks
Price: $26.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Island Style One-Shoulder Slit Tropical Maxi Dress
Get that tropical feeling when you're in this one-shoulder maxi dress, whether you're on vacay or having some weekend fun! The curve-hugging silhouette offers a show of skin with a side cutout and high slit.
Fit & Features
- Tropical print, stretchy knit fabric, short knit lining
- One-shoulder neckline
- Side cutout
- High side slit
- Curve-hugging silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-6089
Category Name: Vacation Looks
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sweet Escape Floral Tie Front Top
Giving off total romantic vibes, this floral top is flirty without trying too hard. With lace trim, long sleeves, and a tie-front detail, it’s the perfect blend of dreamy and effortless.
Fit & Features
- Floral print, mesh fabric, bust knit lining
- Long sleeves
- Lace trim tie-front design
- Ruffled trim, crop hem
- Runs true to size
Style Number/Barcode: 06202-000044
Category Name: Vacation Looks
Price: $15.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Up A Notch Cork Platform Block Heels
Kick your outfit up a notch in these cork platform heels for showers, birthdays, or graduations! These quirky heels feature a square toe and faux leather wide strap for a unique touch. The cork platform sole and block heel provide added height, while the faux leather adjustable ankle strap with buckle closure ensures a comfortable fit. Complete the look with a crossbody purse.
Fit & Features
- 4.5" Cork Block Heel
- Square toe
- Cork platform sole
- Faux leather straps
- Adjustable ankle strap, buckle closure
- Runs true to size
Style Number/Barcode: 07401-4853
Category Name: Vacation Looks
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Make Some Noise Strapless Printed Bustier
Prepare to receive all the compliments when you're in this strapless printed bustier on vacay or a weekend away! Featuring a chic strapless sweetheart neckline with a padded bust, a stretchy smocked back, and a fitted cropped hem, this top is perfect for any occasion. The beautiful watercolor print on the lightweight linen-blend fabric adds a touch of art. Complete the look with the matching palazzo pants.
Shop Matching Bottoms: Make Some Noise Printed Palazzo Pants
Fit & Features
- Watercolor print
- Linen-blend woven fabric with woven lining
- Strapless sweetheart neckline, padded bust
- Stretchy smocked back
- Fitted cropped hem
- Runs true to size
Style Number/Barcode: 06003-2408
Category Name: Vacation Looks
Price: $6.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweet Silhouette Drop Waist Skater Dress
You'll be ready to frolic and twirl with the sweet silhouette of this short skater dress. The tie-back halter straps offer an adjustable fit, while the V-shaped drop waist creates a flattering fit.
Fit & Features
- Poplin woven fabric, woven lining, no stretch
- Sleeveless V-neckline
- Tie-back halter straps, partially open back, zipper with hook-eye closure
- Faux button-down front, pleated accents
- V-shaped drop waist
- Short skater silhouette
- Runs true to size
Style Number/Barcode: 05101-3996
Category Name: Vacation Looks
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free