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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Romantic Vibes Floral Mesh Midi Dress
Hey babe, bring the romantic vibes to your next dinner date in this floral mesh midi dress! It features a sleeveless cowl neckline, bungee spaghetti straps, and a mid-length, curve-hugging silhouette. The sheer mesh fabric has a pretty all-over floral print with a full knit lining. Complete the look with strappy heels.
Fit & Features
- Sleeveless cowl neckline
- Bungee spaghetti straps
- Mid-length, form-hugging fit
- Sheer mesh fabric, knit lining, floral print
- Moderate stretch
- Runs true to size
Style Number/Barcode: 05101-1094
Category Name: Vacation Looks
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Daring Diva Open Back Midi Dress
Dare to go bold with a midi dress that wows! The dress features a sleeveless scoop neckline, adjustable spaghetti straps that cross at the back, and a midi-length silhouette. Complete look with stilettos and door knocker earrings.
Fit & Features
- Sleeveless scoop neckline
- Adjustable spaghetti straps, cross at back
- Open back
- Midi length silhouette
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1210
Category Name: Vacation Looks
Price: $6.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Adventure Awaits Panama Hat
Look oh-so-chic as you set out on your next adventure in this trendy Panama hat. It features a wide flat brim and a thin band with a tie accent. Style this hat with a cute crossbody purse.
Fit & Features
- Wide flat brim
- Thin band, tie accent
- Faux wool material
Style Number/Barcode: 07302-0385
Category Name: Vacation Looks
Price: $10.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Out And About Panama Hat
Get ready to look stylish and chic as you are out and about with this on-trend Panama hat! It features a wide flat brim and a basic ribbon band. Pair this hat with sleek hoop earrings.
Fit & Features
- Wide flat brim
- Basic ribbon band
- Faux wool material
Style Number/Barcode: 07302-0384
Category Name: Vacation Looks
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Chic Crew Ribbed Knit Mini Dress
Show em' all that you roll with the chic crew in this fab mini dress! The dress features a crew neckline with a racer bust, a ruched body, and a mini side slit. The dress is composed of a ribbed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with mules and a denim jacket.
Fit & Features
- Sleeveless crew neckline
- Racer bust
- Ruching
- Mini side slit
- Ribbed knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4240
Category Name: Vacation Looks
Price: $6.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Stylish And Sleek Panama Hat
Top off your look with this stylish Panama hat for an effortless trendy vibe! It features a wide flat brim and a thin adjustable ribbon band with a sleek triangle-shaped buckle. Complete the outfit with cute ankle booties.
Fit & Features
- Wide flat brim
- Thin adjustable ribbon band
- Triangle-shaped buckle
- Faux wool material
Style Number/Barcode: 07302-0386
Category Name: Vacation Looks
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Major Sparkle Rhinestone Slides
Bring a sparkly style to your everyday look with these fab embellished slides. They feature an open square toe, a wide toe strap with all-over rhinestone embellishment, and a glam chrome sole. Pair these slides with a trendy ring pack.
Fit & Features
- Open square toe
- Wide toe strap, rhinestone embellishment
- Chrome sole
- Runs true to size
Style Number/Barcode: 07404-0927
Category Name: Vacation Looks
Price: $10.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sleek And Strappy Studded Jelly Sandals
Keep it sleek and stylish with sandals that slay your look! The sandals feature an adjustable ankle strap, multiple straps, pyramid-shaped studs, and an open almond toe. Complete look with a denim mini dress and hoops.
Fit & Features
- Adjustable ankle strap
- Multiple strap design
- Pyramid-shaped studs
- Open almond toe
- Jelly material
- Runs true to size
Style Number/Barcode: 07404-0832
Category Name: Vacation Looks
Price: $7.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Major Stunner Cutout Midi Dress
Stand out like the major stunner you are with a midi dress that brings the style! The dress features a plunging halter neck with a V-neck bust, a cutout at the midriff with sleek straps, and a midi-length silhouette with a high side slit. The dress is composed of a lurex knit fabric that offers a form hugging fit with a moderate stretch. Complete look with mules.
Fit & Features
- Halter neck, V-neck bust
- Cutout at the midriff with straps
- Midi length silhouette
- High side slit
- Lurex knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4157
Category Name: Vacation Looks
Price: $19.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Reign In Glam Rhinestone Sandals
Reign in luxe with sandals that show how extra you are! The sandals feature a slip-on design, rhinestone embellished straps, an asymmetrical strap, and an open almond toe. Complete look with a ruched mini dress and hoops.
Fit & Features
- Slip-on design
- Rhinestone embellished straps
- Asymmetrical strap
- Open almond toe
- Faux leather material
- Runs true to size
Style Number/Barcode: 07404-0930
Category Name: Vacation Looks
Price: $7.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Banded Panama Hat
Bring your look together with this trendy panama hat! The hat features a panama design and a banded hem around the brim. Complete the look with a romper and sandals.
Fit & Features
- Panama design
- Wide brim
- Banded hem
Style Number/Barcode: 07302-0381
Category Name: Vacation Looks
Price: $8.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Rhinestone Hoops And Studs Six Earring Pack
Add a hint of sparkle to your look with a dazzling pair of earrings! The variety pack includes six pairs of earrings. The earrings feature rhinestone embellished hoops that come in varying sizes, rhinestone studs, butterfly studs, and cross charm studs. Complete look with a white dress and wedges.
Fit & Features
- Pack includes six pairs of earrings
- Hoops in varying sizes
- Rhinestones
- Butterfly studs
- Cross charm studs
Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.
Style Number/Barcode: 07001-0842
Category Name: Vacation Looks
Price: $6.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Blissful Cutie Halter Cutout Skater Dress
Get swept off your feet in this cute skater dress for any casual occasion! With its halter neckline and cutout bodice, this dress is designed to show off your figure, while the ruffled mini-length hem adds a flirty touch.
Fit & Features
- Gauze woven fabric, woven lining
- Halter neckline with spaghetti strap ties
- Stretchy smocked bust
- Cutout bodice
- Ruffled skater silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-6016
Category Name: Vacation Looks
Price: $9.97 $46.90
On Sale: Yes
Availability: In Stock
Available Color: BLUE
Available Size: S, L
Product Badge:- Sale
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Dainty Details Cubic Zirconia Teardrop Necklace
Showcase dainty details with a layered necklace that brings the glam to your outfit! The necklace features a two-row layered design, a round-shaped cubic zirconia stone, a teardrop-shaped cubic zirconia stone, and a lobster clasp closure. Complete look with matching coordinates and heels.
Fit & Features
- Dainty chain link
- Two-row design
- Round-shaped zirconia stone
- Teardrop-shaped zirconia stone
- Lobster clasp closure
Style Number/Barcode: 07002-0845
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Dainty Chain Coin Charm And Cross Necklace Set
Layer on the style with a trendy necklace that brings the glam to your look! The pack includes four necklaces that create a layered five-row design, two coin charms, and a rhinestone embellished cross charm. Complete look with a bustier and high waist jeans.
Fit & Features
- Pack includes four necklaces
- Dainty chain link, snake chain
- Two coin charms
- Cross charm
- Rhinestones
- Lobster clasp closure
Style Number/Barcode: 07002-0849
Category Name: Vacation Looks
Price: $7.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Vacay Queen Espadrille Platform Sandals
Yes babe, you'll be a total vacay queen on your next getaway in these trendy platform sandals! They feature an open round toe, faux leather straps with an adjustable ankle strap, and an espadrille platform with a flat sole. Style these sandals with a floral dress and cute sunnies.
Fit & Features
- Open round toe
- Faux leather straps
- Adjustable ankle strap, buckle detail
- Espadrille platform, flat sole
- Runs true to size
Style Number/Barcode: 07404-0920
Category Name: Vacation Looks
Price: $13.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Blooming Beauty Ditsy Floral Cutout Mini Dress
Let your beauty bloom with a gorge mini dress that reveals your sweet side! The dress features a ditsy floral print, a sleeveless V-neckline, a ruched drawstring at the center, spaghetti straps, a cutout at the midriff, and a mini-length silhouette. The dress is composed of a smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with mules and a denim jacket.
Fit & Features
- Ditsy floral print
- Sleeveless V-neckline
- Ruched drawstring at the bodice
- Spaghetti straps
- Cutout at midriff
- Mini length silhouette
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05102-4126
Category Name: Vacation Looks
Price: $19.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Effortless Flowy A-Line Mini Dress
Get an effortless look in this flowy boho-chic mini dress. It features a sleeveless subtle square neckline, adjustable spaghetti straps that lead to a cross-back design, a short A-line silhouette, and a drop hem with a cute ruffle detail. Style this dress with your fave pair of wedges.
Fit & Features
- Sleeveless square neckline
- Adjustable spaghetti straps
- Cross-back design
- Mini-length, A-line silhouette
- Drop hem, ruffle detail
- Double-lined gauze fabric
- Runs true to size
Style Number/Barcode: 05102-3099
Category Name: Vacation Looks
Price: $20.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Living Large Floppy Straw Hat
Live it up with a straw hat that is perf for your next vacay! The hat features an over straw material, a wide brim, and a cute ribbon-like accent on the brim. Complete look with a white dress and sandals.
Fit & Features
- All over straw material
- Wide brim
- Ribbon-like accent around brim
Style Number/Barcode: 07302-0348
Category Name: Vacation Looks
Price: $15.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Denim Dreams Lace-Up Mini Dress
Keep it dreamy with a denim mini dress that elevates your look! The dress features a sleeveless scoop neckline, spaghetti straps that lead to a lace-up back, vertical seams, and a mini-length silhouette. The dress is composed of a denim fabric that offers a form-hugging fit with a moderate stretch. Complete look with mules.
Fit & Features
- Sleeveless scoop neckline
- Spaghetti straps
- Lace-up back, lower back zipper and hook and eye closure
- Vertical seams
- Mini-length silhouette
- Denim fabric, form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4089
Category Name: Vacation Looks
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Luxe Life Top Handle Bag
Hey babe, live that luxe life with this chic top handle bag! It features a round design with a wide top handle, a zipper closure, a circular buckle detail, and a detachable shoulder strap to change the bag to a crossbody. The faux leather material has a fab croc-embossed print for a trendy vibe. Style this bag with a pair of oversized sunglasses.
Fit & Features
- Round design
- Wide top handle
- Zipper closure
- Circular buckle detail
- Detachable shoulder strap
- Faux leather material, croc-embossed print
Style Number/Barcode: 07203-0770
Category Name: Vacation Looks
Price: $11.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Floral Dreams High-Slit Maxi Dress
This dress is what floral dreams are made of! The dress features a ditsy floral print, a sleeveless sweetheart neckline, a mini tie-front, adjustable spaghetti straps, and a maxi-length silhouette with a high side slit. The dress is composed of a chiffon fabric that offers a relaxed fit with minimal stretch. Complete look with sandals.
Fit & Features
- Sleeveless sweetheart neckline
- Mini tie-front, adjustable spaghetti straps
- Back zipper and hook and eye closure
- Ditsy floral print
- Maxi-length silhouette, high side slit
- Chiffon fabric, knit lining, relaxed fit, minimal stretch
- Runs true to size
Style Number/Barcode: 05101-1074
Category Name: Vacation Looks
Price: $5.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Ravishing Florals Ruched Mini Dress
Stun with ravishing florals in a pretty mini dress! The dress features a sleeveless V-neckline, adjustable spaghetti straps, dual ruching that runs from the bodice to hem, a ditsy floral print, and a mini-length silhouette. The dress is composed of a lined mesh fabric that offers a form hugging fit with a moderate stretch. Complete look with wedges.
Fit & Features
- Sleeveless V-neckline
- Adjustable spaghetti straps
- Dual ruching
- Ditsy floral print
- Mini length silhouette
- Lined mesh fabric
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05102-4151
Category Name: Vacation Looks
Price: $6.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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So Sweet Ruffled Cutout Skater Dress
Keep it so sweet with a charming ruffled skater dress! The dress features an off-the-shoulder neckline, a smocked bodice with a ruched drawstring, long sleeves, a sexy cutout at the midriff, and a tiered ruffled skater silhouette. The dress is composed of a lightweight gauze knit fabric that offers a relaxed fit with minimal stretch. Complete look with sandals.
Fit & Features
- Off-the-shoulder neckline
- Smocked bodice with a ruched drawstring
- Long sleeves, elastic cinched hems
- Cutout at the midriff
- Tiered ruffle skater skirt
- Gauze knit fabric, relaxed fit, minimal stretch
- Runs true to size
Style Number/Barcode: 05101-2486
Category Name: Vacation Looks
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale