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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STYLE SPOTLIGHT

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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.

Bohemian Chic Ruffled A-Line Mini Dress
Channel your bohemian side with a pretty mini dress that channels those lowkey vibes. The dress features a sleeveless square neckline, tie-up shoulder straps, tiered ruffles, and a mini-length A-line silhouette. Complete look with cork wedges.

Fit & Features
- Sleeveless square neck
- Tie-up shoulder straps
- Tiered ruffles
- Mini length
- A-line silhouette
- Relaxed fit, minimal stretch
- Runs true to size
Style Number/Barcode: 05101-1046

Category Name: Vacation Looks

Price: $9.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Vacay Bound Faux Wool Panama Hat
Set out for a vacay with a hat to dress up tresses with! The hat features a traditional Panama design, a faux leather trim around the brim, and a short brim. The hat is composed of a faux wool material. Complete look with a denim jacket and cropped tank.

Fit & Features
- Panama design
- Faux leather trim
- Short brim
- Faux wool material
Style Number/Barcode: 07302-0304

Category Name: Vacation Looks

Price: $6.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Ring It Out Crochet Crop Top
Stand out with a crochet top that brings stylish deets! The top features a trendy boat neckline, long bell sleeves, an unlined crochet-knit body, and a cropped hem. Complete look with high waist shorts.

Fit & Features
- Boat neckline
- Long bell sleeves
- Unlined
- Crochet-knit
- Cropped hem
- Relaxed fit, minimal stretch
- Runs true to size
Style Number/Barcode: 06005-0948

Category Name: Vacation Looks

Price: $6.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Key To Paradise One Piece Swimsuit
Unlock your vacay dreams with a one-piece swimsuit that brings those tropical vibes. The swimsuit features a plunging halter neckline with a fasten at the neck, a bold open back, a tropical print, and a cheeky bottom. Complete look with a floppy hat and slides.

Fit & Features
- Plunging halter neckline
- Open back
- Tropical print
- Cheeky bottom
- Form hugging fit
- Runs true to size
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07109-0238

Category Name: Vacation Looks

Price: $5.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Dainty Details Faux Leather Lace-Up Block Heels
The details make these heels a stunning accent to your look! The heels feature sleek lace-up straps, an open back, sleek asymmetrical straps over the toe, an open square toe, and a low block heel. The heels are composed of a faux leather material. Complete look with a white mini dress and butterfly earrings.

Fit & Features
- Lace-up straps
- Open back
- Asymmetrical straps over the toe
- Open square toe
- Low block heel
- Faux leather material
Style Number/Barcode: 07401-2767

Category Name: Vacation Looks

Price: $15.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Classic Vibes Strappy Sandals
Bring the classic vibes to your summer look with these chic strappy sandals. They feature an open round toe, a thick toe strap, an adjustable ankle strap, and a cool metallic detailed edge. Complete the outfit with a must-have crossbody purse.

Fit & Features
- Open round toe
- Thick toe strap
- Adjustable ankle strap
- Metallic detailed edge
- Flat sole
- Black sandals are faux microsuede, nude sandals are PU
- Runs true to size
Style Number/Barcode: 07404-0728

Category Name: Vacation Looks

Price: $12.97 $14.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Such A Gem Butterfly Jelly Sandals
Bring the glam to your summertime outfits with these butterfly jelly sandals. They feature an open almond toe with a thong strap design, a sparkly center butterfly gemstone design, an adjustable ankle strap, and an all-over metallic finish. Complete the look with a pretty charm necklace.

Fit & Features
- Open almond toe
- Thong strap design
- Center butterfly gemstone design
- Adjustable ankle strap
- Flat sole
- All-over metallic finish
- Runs true to size
Style Number/Barcode: 07404-0761

Category Name: Vacation Looks

Price: $7.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Stylishly Smocked Off-The-Shoulder Romper
Level up your summer style with this flirty smocked romper! It features an off-the-shoulder neckline with a ruffle trim, short sleeves, a tie-front detail, a fitted smocked bodice, and flowy shorts. Complete the look with strappy sandals and a woven tote.

Fit & Features
- Off-the-shoulder neckline, ruffle trim
- Short sleeves
- Tie-front detail
- Fitted smocked bodice
- High waist, flowy shorts
- Woven fabric
- Runs true to size
Style Number/Barcode: 06303-0099

Category Name: Vacation Looks

Price: $6.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
So Glam Tie Dye Ruched Mini Dress
Keep it so glam with a tie-dye dress that gives your look a retro feel! The dress features a sleeveless square neckline, bungee spaghetti straps, a tie-dye print, a ruched side seam, and a mini-length silhouette. The dress is composed of a brushed knit fabric that offers a form-hugging fit with a moderate stretch. Complete the look in new top-rated shoes.

Fit & Features
- Sleeveless square neckline
- Bungee spaghetti straps
- Tie-dye print
- Ruched side seam
- Mini length silhouette
- Brushed knit fabric
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05102-1083

Category Name: Vacation Looks

Price: $6.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Glam And Edgy Studded Bow Sandals
Part edgy, part glam, these sandals are a must! The sandals feature a clear PVC T-strap embellished with studs, a bow accent, and a nailhead trim. Complete look with a ruffled mini dress and a floppy hat.

Fit & Features
- Clear PVC T-strap
- Studs
- Bow accent
- Nailhead trim
- Faux leather insole
Style Number/Barcode: 07404-0787

Category Name: Vacation Looks

Price: $12.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sealed With Glam Thong Strap Jelly Sandal
Seal your look with luxe sandals that bring the sparkle! The sandals feature a rhinestone embellished thong strap, a pretty bow accent, and a matching rhinestone and gemstone trim. Complete look with a crop top and denim shorts.

Fit & Features
- Thong strap design
- Almond toe
- Bow accent
- Rhinestones
- Gemstones
- Jelly material
Style Number/Barcode: 07404-0788

Category Name: Vacation Looks

Price: $12.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Such A Sweetheart Corset Lace-Up A-Line Short Dress
Capture sweet vibes in this flirty corset short dress designed with a striking lace-up back design, a corset-style bodice that snatches your waist, and a flattering A-line silhouette. Pair with bow earrings.

Fit & Features
- Poplin woven fabric, woven lining
- Sweetheart neckline with adjustable drawstring tie
- Adjustable spaghetti straps, lace-up back design
- Underwire bust, corset-bodice, flexible boning
- Side zipper and hook-eye closure
- A-line short silhouette
- Runs true to size
Style Number/Barcode: 05101-3779

Category Name: Vacation Looks

Price: $9.97 $48.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Chic Cutout Ribbed Swim Top
Bring the chic vibes to your poolside look in this trendy ribbed swim top! It features tank shoulder straps, a scoop neckline, and a center front cutout at the bust with dual tortoise-shell O-ring accents. Complete the look with the matching swim bottoms and a flowy duster.

Shop Matching Swim Bottoms: Chic Cutout Ribbed Swim Bottoms

Fit & Features
- Tank shoulder straps
- Scoop neckline
- Center front cutout at the bust
- Dual tortoise-shell O-ring accents
- Dual back straps
- Ribbed fabric
- Runs true to size
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07104-0489

Category Name: Vacation Looks

Price: $9.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Good Vibes High-Rise Denim Shorts
Bring the good vibes this summer with these classic high-rise denim shorts! They feature a traditional five-pocket and belt loop design, a front button and hidden zipper closure, destructed details, and a frayed hem. Pair these shorts with a graphic tee and sneakers for the perf casual everyday outfit.

Fit & Features
- High-rise waist
- Traditional five-pocket and belt loop design
- Front button and hidden zipper closure
- Distressed details
- Frayed hem
- Denim fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06603-0187

Category Name: Vacation Looks

Price: $6.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Vintage Vibes Acid Wash Denim Shorts
Showcase those trendy vintage vibes with these acid wash denim shorts. They feature a high-rise waist, a traditional five-pocket and belt loop design, a front button and hidden zipper closure, and a cutoff hem. Pair these shorts with a graphic tee and booties for an edgy summer look.

Fit & Features
- High-rise waist
- Traditional five-pocket and belt loop design
- Front button and hidden zipper closure
- Cutoff hem
- Acid wash denim fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06603-0188

Category Name: Vacation Looks

Price: $9.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Find Me In Paradise Swim Top
Find yourself in paradise in this swim top that will have you looking stunning as you relax on the beach! It features tank shoulder straps, a tie-front, a tie detail at the back, and a pretty all-over tropical floral print. Complete your look with the matching swim bottoms and chic sunnies.

Shop Matching Swim Bottoms: Find Me In Paradise Swim Bottoms

Fit & Features
- Tank shoulder straps
- Tie-front
- Tie detail at the back
- Tropical floral print
- Runs true to size
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07104-0370

Category Name: Vacation Looks

Price: $8.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Find Me In Paradise Swim Bottoms
Find yourself in paradise in these swim bottoms that will have you looking stunning as you relax on the beach! They feature a high-rise waist, side tie details, a semi-cheeky fit, and a pretty all-over tropical floral print. Complete your look with the matching swim top and chic sunnies.

Shop Matching Swim Top: Find Me In Paradise Swim Top

Fit & Features
- High-rise waist
- Side tie details
- Semi-cheeky fit
- Tropical floral print
- Runs true to size
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07105-0519

Category Name: Vacation Looks

Price: $8.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Studded Stunner Thong Strap Bow Sandals
Part edgy, part glam, these sandals are a must! The sandals feature a thong strap embellished with studs, a bow accent, and a flat sole. Complete the look with a ruffled mini dress and a floppy hat.

Fit & Features
- PVC thong strap
- Studs
- Bow accent
Style Number/Barcode: 07404-0786

Category Name: Vacation Looks

Price: $9.97 $14.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Dainty And Chic Two-Pack Necklace Set
Layer on this dainty and chic necklace set to add a subtle hint of glam to your look. The set features two necklaces, the shorter necklace with a small center rhinestone cross charm, and the longer necklace with a cascading lariat with a bigger rhinestone cross charm. Complete the look with stud earrings and a chic tennis bracelet.

Fit & Features
- Two-pack necklace set
- Dainty chains
- Rhinestone cross charms
- Lariat accent
Style Number/Barcode: 07002-0709

Category Name: Vacation Looks

Price: $3.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Butterfly Charm Ruched Mini Dress
Bring the charm with a butterfly print dress that springs you into the season. The mini dress features a sleeveless square neckline, spaghetti straps, a butterfly print, a ruched body, 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 butterfly earrings and wedges.

Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Butterfly print
- Ruched body
- Mini-length silhouette, form-hugging fit
- Lined knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-1454

Category Name: Vacation Looks

Price: $9.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Effortless Style Tie-Front Maxi Dress
Showcase a chic effortless style this season with this adorable maxi dress! It features a sleeveless V neckline, adjustable spaghetti straps, a tie-front detail with a small cutout, center button accents, and a flowy fit with a center slit. Pair this ribbed knit dress with a straw tote and strappy sandals.

Fit & Features
- Sleeveless V neckline
- Adjustable spaghetti straps
- Tie-front, small cutout
- Fitted bodice
- Center button details
- Flowy silhouette, center slit
- Ribbed knit fabric
- Runs true to size
Style Number/Barcode: 05102-1174

Category Name: Vacation Looks

Price: $21.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Chic Stunner Stiletto Mules
Complete your outfits with this chic and stunning pair of stiletto mules! They feature an on-trend square toe, criss-cross straps with a quilted design, and a sleek stiletto heel. Style these mules with denim and a cute corset top.

Fit & Features
- Square toe
- Criss-cross straps
- Quilted design
- Stiletto heel
- PU material
- Runs true to size
Style Number/Barcode: 07401-2631

Category Name: Vacation Looks

Price: $7.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sweet Vibes Tie-Front Bodysuit
This adorable bodysuit will bring sweet vibes to your summer style! It features wide shoulder straps, a sweetheart neckline with a tie-front detail, and a fitted silhouette. Complete the look with cutoff denim shorts and cute sandals.

Fit & Features
- Wide shoulder straps
- Sweetheart neckline
- Tie-front
- Cheeky bottom, dual snap-button closure
- Form-hugging fit
- Ribbed knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06001-3213

Category Name: Vacation Looks

Price: $6.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Fab And Frayed High Waist Denim Shorts
Keep it fab with denim shorts that are perf for those casual days out! The shorts feature a high-rise waist, a single button with zipper closure, a traditional five-pocket with belt loop design, light distressing, and a frayed hem. Complete the look with a cute tank and sandals.

Fit & Features
- High rise waist
- Single-button with zipper closure
- Traditional five-pocket with belt loop design
- Light distressing
- Frayed hem
Style Number/Barcode: 06603-0168

Category Name: Vacation Looks

Price: $9.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale

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Vacation Looks

HomeVacation Looks

Now Trending

STYLE SPOTLIGHT

Vacation Dresses & Outfits for Effortless Getaways

Easy, Packable Styles

Day-to-Night Versatility

Resort & Beach Essentials