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.

Cropped Ruched Tie Front Top
Stay on-trend in a ruched crop top. The top features a plunging sweetheart neckline, a tie-front accent, ruched side seams, spaghetti straps, and a cropped hem. The top is composed of a smooth knit fabric that offers a relaxed fit with a moderate stretch. Complete your look with the matching skirt and heels.

Shop Matching Skirt: High Waist Ruched Pencil Skirt

Fit & Features
- Sweetheart neckline, spaghetti straps
- Tie-front accent
- Ruched side seam
- Cropped hem
- Smooth-knit stretch fabric
- Runs true to size
Style Number/Barcode: 06001-2674

Category Name: Vacation Looks

Price: $6.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
High Waist Ruched Pencil Skirt
Stay on-trend in a ruched pencil skirt. The must-have skirt features a high-rise waist, ruched side seams that flatter curves, and a pencil skirt silhouette. The skirt is composed of a smooth knit fabric that offers a form-hugging fit with a moderate stretch. Complete outfit with matching top and heels.

Shop Matching Top: Cropped Ruched Tie Front Top

Fit & Features
- High-rise waist
- Ruched side seams
- Pencil silhouette
- Smooth knit fabric
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06501-0279

Category Name: Vacation Looks

Price: $9.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Stuck on Floral Maxi Dress
Have a floral moment in this flowy maxi dress! Style it with hoops and wedges for the perfect day date look.

Fit & Features
- Off the Shoulder
- Double Front Slits
- Maxi Length
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05101-0632

Category Name: Vacation Looks

Price: $9.97 $38.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Puff Sleeve Ruched Knit Mini Dress
Keep on trend in a puff sleeve dress. This must-have dress features a sweetheart neckline with ruched detailing, puff sleeves, and a mini length silhouette. The dress is composed of a knit fabric that offers a form hugging fit with a slight stretch. Complete look with a pair of pumps and earrings.

Fit & Features
- Sweetheart neckline
- Ruched detailing at the bust
- Short puff sleeves
- Knit fabric
- Form hugging fit
- Moderate stretch
Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0733

Category Name: Vacation Looks

Price: $10.97 $27.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Sleeveless Cut Out O-Ring Ribbed Mini Dress
Step up in a sleeveless ribbed mini dress with sexy cutout details this season. The curve-hugging ribbed dress features a flattering crew neck that leads to a chic O-Ring at the mid-drift accented with waist cut outs for a subtle hint of skin. The back reveals a matching lower back cut out to impress from all angles. The ribbed knit embraces curves while offering a moderate stretch to easily move. Complete this date-night ready look with daring hoops and strappy stilettos.

Fit & Features
- Sleeveless
- Crew neckline
- O-Ring at the center, waist cut outs
- Lower back cut out
- Mini length silhouette
- Ribbed knit fabric
- Form hugging fit, moderate stretch
Style Number/Barcode: 05102-0723

Category Name: Vacation Looks

Price: $9.97 $28.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Floral Stunner Midi Dress
Be a stylish stunner in this gorg floral midi dress! It features a sleeveless bodice, adjustable spaghetti straps that cross in the back, a V neckline, side ruched detailing, and an asymmetrical hem. The dress is composed of a knit fabric that offers plenty of stretch.

Style Number/Barcode: 05102-3848

Category Name: Vacation Looks

Price: $13.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Take a Trip Tropical Mini Dress
You’ll be ready for date night on the beach in this tropical print mini dress. Style it with clear heels and hoops for an effortless look.

Fits & Features
- V-Neckline
- Spaghetti Straps
- Asymmetrical Hem
Model is 5'9" with a 32" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0440

Category Name: Vacation Looks

Price: $9.97 $33.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Sassy Smocked Crop Top
Ooo girl, you'll be lookin' sassy in this smocked crop top! Pair with the matching mini skirt for the perf look for a sunny day out!

Shop Matching Bottoms: Sassy Smocked Mini Skirt

Fit & Features
- Spaghetti straps
- V neckline
- Cropped merrow edge hem
- Smocked knit fabric
Style Number/Barcode: 06001-2423

Category Name: Vacation Looks

Price: $6.97 $14.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Ruffled Eyelet Puff Sleeve Mini Dress
Keep it chic in an eyelet mini dress. This season-ready dress features a sweetheart neckline, a tie front accent, short puff sleeves, and ruched vertical seams that highlight and enhance curves. The relaxed waist leads to a ruffled hem. The dress is composed of a lightweight knit fabric with an eyelet pattern. The dress is composed of a lightweight woven fabric that offers a relaxed fit with minimal stretch. Complete your look with wedges and fringe earrings.

Fit & Features
- Sweetheart neckline
- Tie front accent
- Short puff sleeves
- Vertical seams
- Eyelet design
- Ruffled hem
- Lightweight woven fabric, relaxed fit
Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0734

Category Name: Vacation Looks

Price: $9.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Feeling Floral Eyelet Mini Dress
We’re always in the mood for a little floral print! Pair this mini dress with sandals and layered dainty jewelry.

Fit & Features
- All Over Eyelet Design
- Ditsy Floral Print
- Mini Length
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05102-0709

Category Name: Vacation Looks

Price: $9.97 $25.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Tropical Getaway Sleeveless Asymmetrical Ruched Midi Dress
Head to the tropics in this midi dress that brings a tropical burst of color. This vacation-ready dress features a sleeveless bodice, a plunging V-neckline and adjustable spaghetti straps that lead to an X-back design. The relaxed fit waist leads to a midi length silhouette with a ruched side seam and an asymmetrical high slit to show off a hint of skin. The all-over tropical print features bright hues that perfectly complement the neutral background. The dress is composed of a smooth knit fabric that offers a form-hugging fit. Complete your look with a pair of heels and golden hoop earrings.

Fit & Features
- Plunging V-neckline
- Adjustable spaghetti straps
- X-back
- Midi length silhouette
- Tropical print
- Asymmetrical high side slit
- Form hugging fit
Model is 5'6" with 31" bust, 26" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0579

Category Name: Vacation Looks

Price: $9.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Perfect Pair Bow Detail Thong Strap Sandals
The perfect pair of sandals for casual weekend plans! The thong strap design features a bow accent for the cutest detail.

Fit & Features
- Faux leather material
- Almond-shaped toe
- Thong strap design, bow detail
- Open back, on-and-off styling
- Flat sole
- Runs true to size
Style Number/Barcode: 07404-1253

Category Name: Vacation Looks

Price: $9.97 $14.90

On Sale: Yes

Availability: In Stock

Available Color: SILVER

Available Size: 7.5, 8.5
Product Badge:
- Sale
Ribbed Knit Ruffled Ditsy Floral Mini Dress
Slay in a gorge ditsy floral mini dress. A ditsy floral dress is a staple piece to have for brunch or a day date with bae. This must-have features a sleeveless sweetheart neckline with a tie-front accent and ruffled trim with matching ruffled spaghetti straps. The relaxed fit waist leads to a curve-hugging mini-length silhouette. The dress is composed of ribbed knit fabric that offers a moderate stretch. Complete your floral look with cork wedges and dainty rings.

Fit & Features
- Sleeveless sweetheart neckline
- Tie-front bodice
- Ruffled spaghetti straps
- Ditsy floral print
- Mini length silhouette
- Ribbed knit fabric
- Form hugging fit, moderate stretch
Style Number/Barcode: 05102-0769

Category Name: Vacation Looks

Price: $19.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
3-D Butterfly Headband
This cute headband is giving us major butterflies! This sweet headband features a slim band and 3-D metal butterflies to adorn tresses with. Create a bohemian-inspired look with high waist flared pants and a crochet top.

Fit & Features
- Slim headband
- 3-D metal butterflies
Style Number/Barcode: 07006-0146

Category Name: Vacation Looks

Price: $5.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Do It Better Clear Cork Mules
Do it better when you step out in a pair of sandy cork mules! Styled perfectly with your fav denim they are a new go-to!

Fit & Features
- Open almond toe
- Double pvc bands
- Low block heel
- Cork style sole
Style Number/Barcode: 07401-2209

Category Name: Vacation Looks

Price: $12.97 $25.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Summer Vibes Cork Platform Heels
Step into the season in cork heels that bring those summer vibes. The heels feature an open back, an adjustable ankle strap, an open almond toe with a single strap over the toe, and a cute cork platform. Complete your look with a sundress and sunnies.

Fit & Features
- Open back
- Adjustable ankle strap strap
- Open almond toe
- Single strap over the toe
- Cork platform
- Block heel
Style Number/Barcode: 07401-2192

Category Name: Vacation Looks

Price: $23.97 $28.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
On That Basic Vibe Straw Boater Hat
Rock a basic vibe with a boater hat that brings a casual vibe. The hat features a traditional boater design and a black trim around the brim. Complete look with a fab sundress and sandals.

Fit & Features
- Boater design
- Short brim
- Black trim around the brim
- Straw material
Style Number/Barcode: 07302-0169

Category Name: Vacation Looks

Price: $6.97 $14.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Look At Her Ruched Mini Dress
Draw all eyes on you in this mini dress that stuns! Keep it flirty for your next date-night in this dress that features a plunging sweetheart neckline, clear adjustable straps, and a ruched body throughout that highlights curves in all the right places. Complete your look with clear heels and sparkling rhinestone earrings.

Fit & Features
- Sleeveless sweetheart neckline
- Clear adjustable straps
- Ruched detailed body
- Mini length silhouette
- Form hugging fit, moderate stretch
Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05103-1918

Category Name: Vacation Looks

Price: $15.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Double Drawstring Floral Mini Dress
Bring the charm in a floral dress that brings a sweet vibe this season. The mini dress features a sweetheart neckline, adjustable spaghetti straps, and a floral print. Complete your look with cute cork wedges and dainty anklets.

Fit & Features
- Sleeveless sweetheart neckline
- Adjustable spaghetti straps
- Floral print
- Drawstring at the side seams
- Mini length silhouette
- Form hugging fit
Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05101-0878

Category Name: Vacation Looks

Price: $9.97 $49.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Stunning In Florals Sleeveless Midi Dress
Be a stylish stunner in this gorg floral midi dress! Step out for brunch with the squad in this colorful midi dress. It features a sleeveless bodice, adjustable spaghetti straps that cross in the back, a V neckline, side ruched detailing, and an asymmetrical hem. Complete look with wedges.

Fit & Features
- Sleeveless v-neckline
- Adjustable spaghetti straps
- Crossback straps
- Floral print
- Ruched side seam
- Midi length silhouette with asymmetrical hem
- Form hugging fit, plenty of stretch
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0292

Category Name: Vacation Looks

Price: $13.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Romanced in Ruffles A-Line Mini Dress
Fall for this ruffled dress as you have em' fall for you girl! Step out for a day-date in this mini dress that features a ruffled off the shoulder neckline with a sweetheart bust, a cute tie-front accent, and an A-line mini length silhouette with ruffled hem. Complete your look with sunnies and wedges.

Fit & Features
- Ruffled off the shoulder neckline
- Sweetheart bust with tie-front accent
- Mini length A-line silhouette
- Ruffled hem
- Form hugging fit
Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0811

Category Name: Vacation Looks

Price: $9.97 $46.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Walk My Way Rhinestone Strappy Sandals
Take a walk on the beach in these sparkling beauties! They bring out your true goddess when you style with a long maxi dress!
- Open almond toe
- Criss cross strappy detailing
- Rhinestone embellished
- Faux leather lining
Style Number/Barcode: 07404-0591

Category Name: Vacation Looks

Price: $12.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Essential Basic Strap Espadrille Heels
Strap up in these espadrille heels that give off major summer vibes! They feature an open back, an adjustable ankle strap, an open almond toe with a wide strap over the toe, and an espadrille sole. Complete look with a flowy maxi dress.

Fit & Features
- Open back
- Adjustable ankle strap
- Open almond toe
- Wide strap over the toe
- Espadrille sole
Style Number/Barcode: 07406-0083

Category Name: Vacation Looks

Price: $12.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Basic Strap Espadrille Sandals
Strap up in cute espadrille sandals this season. Own those casual vibes with a flowy maxi dress for a fab day out. The sandals feature an adjustable ankle strap, a single strap over the toe, and an espadrille sole.

Fit & Features
- Adjustable ankle strap
- Open almond toe
- Single strap over the toe
- Espadrille sole
- Composed of a faux nubuck material
Style Number/Barcode: 07404-0529

Category Name: Vacation Looks

Price: $12.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free

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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