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.

Fit To Bloom Scoop Neck Ditsy Floral Midi Dress
Sweet summer events are calling and this ditsy floral midi dress is here to make you look cute! Adjustable spaghetti straps and a drawstring scoop neckline provide versatile style, while the form-hugging fit and side slit add a touch of sass. Complete the look in high heels.

Fit & Features
- Ditsy floral print, bust lining, knit fabric, moderate stretch
- Spaghetti straps
- Drawstring adjustable scoop neckline, bust tie
- Form-hugging fit
- Side slit
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-5774

Category Name: Vacation Looks

Price: $9.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Daily Cute Vibe Twist V-Neck Crop Top
Always cute every day, this seamless crop top is perfect for creating alluring looks! Made with seamless rib knit fabric, this crop top is not only stylish but also comfortable. The spaghetti straps and V-neckline provide a sleek and sexy silhouette, while the twist bust adds a touch of flirtiness to the cropped hem that shows off your curves. Complete the look in best-selling bottoms and heels.

Fit & Features
- Seamless rib knit fabric, double-lined, moderate stretch
- Spaghetti straps
- V-neckline
- Twist bust
- Cropped length
- Runs true to size
Style Number/Barcode: 07109-0402

Category Name: Vacation Looks

Price: $4.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Always Trending Strapless Striped Bodycon Mini Dress
Trend right in this strapless mini dress featuring a twist sweetheart neckline with a keyhole cutout and a flattering bodycon silhouette. The striped knit material hugs your curves making it perfect for pairing with sneakers or sandals.

Fit & Features
- Striped print, stretchy knit material
- Strapless sweetheart twist neckline
- Keyhole cutout
- Bodycon mini-length hem
- Runs true to size
Style Number/Barcode: 05102-5824

Category Name: Vacation Looks

Price: $9.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Short But Sweet Gingham Bow Shorts
Short but super sweet! These gingham shorts are the cherry on top of a perfect sunny day look featuring a flattering high-rise waist and side bow ties.

Fit & Features
- Gingham print, cotton woven fabric
- High-rise elasticized waist
- Hidden side pockets
- Side bow ties
- Fitted hem
- Runs true to size
Style Number/Barcode: 06303-000017

Category Name: Vacation Looks

Price: $10.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Dainty Luxe Rhinestone Charm Belly Chain
This dainty rhinestone charm belly chain is dotted with shimmering charms—perfect for layering or letting it shine solo on your next night out.

Fit & Features
- Rhinestone charms
- Dainty chain
- Lobster clasp closure
Style Number/Barcode: 07002-000190

Category Name: Vacation Looks

Price: $14.90

Availability: In Stock

Available Color: GOLD

Available Size: NS
Vacay Ready Tropical Knit Halter Crop Top
This alluring tropical halter crop top will have you ready for a dreamy vacay! The lined stretchy knit fabric features a bold abstract tropical print pattern to catch all the glances on your getaway. The crop top is shaped with a sleeveless halter neckline with a sultry V-shaped cutout, tie-back halter straps, ruched side seams to accentuate your curves, and a form-hugging fit for a snatched look. Style with the matching wide-leg pants and hoop earrings.

Shop Matching Bottoms: Vacay Ready Tropical Knit Wide-Leg Pants

Fit & Features
- Abstract tropical print
- Stretchy lined knit
- Halter neckline, V-shaped cutout
- Tie-back spaghetti straps
- Ruched side seams
- Fitted cropped hem
- Runs true to size
Style Number/Barcode: 06001-5210

Category Name: Vacation Looks

Price: $6.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Beachy-Chic Shell Thong Strap Sandals
These beachy-chic shell thong strap sandals are a style staple for your summer vacay! Made with faux leather, they feature an almond toe, a trendy thong strap design with sleek oval-shaped shell accents, thin adjustable ankle and heel straps with a buckle closure, and a flat sole for comfortable wear. Pair with a crochet top and denim shorts!

Fit & Features
- Faux leather upper
- Almond toe
- Thong strap design
- Oval shell accents
- Adjustable ankle and heel straps with buckle closure
- Flat sole
- Runs true to size
Style Number/Barcode: 07404-1208

Category Name: Vacation Looks

Price: $9.97 $20.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Knit The Beach Striped Strappy Crochet Crop Top
This striped crochet crop top is all about the beach life! Featuring a square neckline, spaghetti straps, and a strappy open back, this top is perfect for summer fun. Its cropped hem adds a trendy touch. Complete the look in denim shorts.

Fit & Features
- Striped pattern, crochet fabric, no stretch
- Square neckline
- Spagehtti strap, strappy open back
- Cropped hem
- Runs true to size
Style Number/Barcode: 06005-2007

Category Name: Vacation Looks

Price: $6.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Girl Next Door Vibes Cropped Tank
Look like the total girl next door in this basic cropped tank. This staple piece goes with everything from your casual looks or as a layering piece for a dressed-up look. The cropped tank features a sleeveless bodice and bungee spaghetti straps for a secure and comfortable fit. Complete your girl-next-door look with high waist jeans and a pair of sneakers.

Shop In More Colors: Girl Next Door Cropped Tank

Fit & Features
- V-neckline
- Bungee straps
- Cropped
- Knit fabric
- Form-hugging fit
- Moderate stretch
- Runs true to size
Style Number/Barcode: 06001-4459

Category Name: Vacation Looks

Price: $6.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Natural Romancer Crew Neck Lace Mini Dress
Indulge in the effortless romance of this lace mini dress perfect for bridal showers, rehearsal dinners, and parties! This stunning dress features short sleeves, a flattering crew neckline, and a bodycon silhouette that hugs your curves. The sheer lace fabric exudes romance, while the attached knit slip lining provides comfort and coverage. Complete the look with earrings and strappy sandals.

Fit & Features
- Sheer lace fabric with stretch
- Attached slip knit lining
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-5548

Category Name: Vacation Looks

Price: $9.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Trendy Ease Strapless Boho Print Wide-Leg Jumpsuit
The perfect strapless boho jumpsuit for every summer adventure that features a stretchy smocked bodice, a braided waist belt, and a flattering wide-leg fit. The sleek knit fabric offers plenty of stretch and a unique boho-print.

Fit & Fetaures
- Boho-print, sleek knit fabric, moderate stretch
- Strapless neckline
- Stretchy smocked bodice
- Braided waist belt
- Wide-leg fit
- Jumpsuit has a 12” front rise with a 29.5” inseam
- Runs true to size
Style Number/Barcode: 06502-2524

Category Name: Vacation Looks

Price: $9.97 $54.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sun-Soaked Halter Open Back Paisley Crop Top
Have a sun-soaked adventure in this paisley crop top this summer! Featuring a flattering halter V-neckline and spaghetti strap ties, along with an open back elasticized bar and a pointed crop hem to show off your figure. Complete the look in jean shorts and sunglasses.

Fit & Features
- Paisley print, knit fabric, minimal stretch
- Halter V-neckline, spaghetti strap ties
- Open back with elasticized bar
- Cropped length
- Runs true to size
Style Number/Barcode: 06003-2552

Category Name: Vacation Looks

Price: $6.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Stylish Striped Halter Crochet Midi Dress
Stay stylish in this striped crochet midi dress for a sunny day by the beach or on vacation! It features a flattering halter neckline, adjustable spaghetti strap ties, and a bodycon fit that accentuates your curves along the midi-length hem. Complete the look with sunglasses and a tote bag!

Fit & Features
- Striped pattern, crochet fabric, short knit stretchy lining
- Halter neckline with spaghetti strap ties
- Bodycon fit
- Midi-length silhouette
- Runs true to size
Style Number/Barcode: 06005-2032

Category Name: Vacation Looks

Price: $6.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Golden Hour Shell Toe Ring Set
Serving seaside glam with zero sand required. This 3-piece shell ring set brings the beach to your fingertips—literally. Stack 'em, mix 'em, or wear solo for a subtle flex.

Fit & Features
- Starfish, cowrie, and conch shell charms
- Coastal-inspired accents
- Pack includes three toe-rings
Style Number/Barcode: 07004-000032

Category Name: Vacation Looks

Price: $2.97 $6.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Versatile Dream Strappy Faux Leather Block Heels
A versatile pair of faux leather heels that can be styled with multiple outfits! They feature a sleek square toe, block heel, and a strappy design for a stylish touch. Complete the look with a trendy tote bag.

Fit & Features
- 3.5" Block heel
- Square toe
- Strappy design
- Faux leather material
- Luxe fit cushioned insole
- Runs true to size
Style Number/Barcode: 07401-4904

Category Name: Vacation Looks

Price: $9.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Flirty Match Short Sleeve Tie-Front Top
Flirt up your style in this crop top on vacation or weekend fun! The flowy short sleeves and cropped hem provide a flattering fit, while the tie-front design adds a touch of playful charm. Complete the look with the matching bottoms.

Shop Matching Bottoms: Flirty Match High-Rise Palazzo Pants

Fit & Features
- Woven fabric, no stretch
- Tie-front design
- Cropped hem
- Runs true to size
Style Number/Barcode: 06204-1752

Category Name: Vacation Looks

Price: $9.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Strolls In The Sand V-Neck Tropical Skater Mini Dress
Getaway in this tropical skater mini dress to the beach or on vacay! Featuring adjustable spaghetti straps and a flattering V-neckline, this dress hugs your silhouette with an elasticized waist and side cutouts. Its skater silhouette and mini-length hem make it perfect for any daytime adventure. Complete the look in cute sandals.

Fit & Features
- Tropical print, woven fabric lined with stretchy knit
- Adjustable spaghetti straps
- V-neckline
- Elasticized waist with side cutouts
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05102-5656

Category Name: Vacation Looks

Price: $9.97 $46.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Perfect Style Cowl Neck Slit Paisley Maxi Dress
Bask in the aesthetic perfection of this paisley mesh maxi dress whether you're on vacation or having a sunset dinner with friends! This form-hugging dress features a cowl neckline and spaghetti straps, highlighting your figure in all the right ways. The high-side slit and sheer maxi-length hem add a touch of allure to this must-have dress! Complete the look with a necklace and earrings.

Fit & Features
- Paisley print, partially lined mesh fabric
- Cowl neckline
- Spaghetti straps
- High side slit
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 05102-5694

Category Name: Vacation Looks

Price: $9.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Casual Times Long Sleeve Striped Button Down Top
Casually update your everyday look in this striped oversized top to pair with your favorite bottoms! It features a collar neckline, long sleeves with button cuffs, a button-down front, and a trendy oversized fit on poplin woven fabric for a polished look. Style this top with jean shorts, sandals, and sunglasses!

Fit & Features
- Striped print, poplin woven fabric, no stretch
- Collar neckline
- Button down front
- Oversized fit
- Runs true to size
Style Number/Barcode: 06003-2627

Category Name: Vacation Looks

Price: $6.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Flirty Moves Ruffled Slit Knit Midi Skirt
Make major flirty moves and create an enticing aura in this ruffled slit midi skirt! Designed with a stretchy smooth knit fabric, it features a high-rise elasticized waist for comfortable wear, ruching down the side seam to accentuate your curves, a sultry high-cut side slit with a ruffled hem, and a bodycon fit along the midi-length silhouette. Style with the matching crop top for a girl's night out!

Shop Matching Top: Flirty Moves Ruffled Tie-Front Knit Crop Top

Fit & Features
- Stretchy smooth knit fabric
- High-rise elasticized waist
- Ruched side seam
- High side slit, ruffled hem
- Bodycon fit
- Runs true to size
Style Number/Barcode: 06501-1042

Category Name: Vacation Looks

Price: $6.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Always Glowing Rhinestone Strap Sandals
Always glow in these rhinestone strap sandals to dress up your everyday look or date night dress!

Fit & Features
- Square toe
- Asymmetrical rhinestone straps
- Flat sole
- Runs true to size
Style Number/Barcode: 07404-1257

Category Name: Vacation Looks

Price: $8.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Looking Good V-Waist Smocked Flare Pants
Looking good will be effortless in these flare pants perfect for vacation or a hot night out! Made of smocked stretchy knit fabric, these pants offer comfort and a flattering silhouette. The cinched mid-rise V-waist and hip-hugging fit will accentuate your curves, while the flared hem adds a touch of flare to your outfit. Complete the look with the matching top.

Shop Matching Top: Looking Good Sweetheart Tie Front Crop Top

Fit & Features
- Stretchy smocked knit fabric
- Mid-rise V-waist with cinch
- Hip-hugging fit
- Flare hem
- Runs true to size
Style Number/Barcode: 06502-2495

Category Name: Vacation Looks

Price: $9.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Kellie Strapless Ruffled Slit Lace Formal Dress
Special Occasion

A showstopping lace formal dress that exudes romance and modern elegance. Designed with a high strapless neckline, this long dress boasts a bodycon silhouette with flirty cascading ruffles and a sultry high-side slit. Complete the look with earrings and heels.

Unapologetically bold, this dress is all about confidence. Keep the luxe look going with our stunning strapless prom dresses or discover the perfect fit among our stylish wedding guest dresses.

Fit & Features
- Lace fabric lined with stretchy knit
- High strapless neckline, non-slip grip lining
- Side zipper and hook-eye closure
- High-side slit
- Bodycon silhouette
- Long-length hem
- Runs true to size
Style Number/Barcode: 05002-8961

Category Name: Vacation Looks

Price: $19.97 $64.90

On Sale: Yes

Availability: In Stock

Available Color: YELLOW

Available Size: L
Product Badge:
- Sale
On The Beach Three-Pack Anklet Set
Take a stylish stroll along the sandy beach wearing this three-pack anklet set. It features two dainty chain link anklets and one chain anklet with a seashell charm. Each has a lobster clasp closure. Complete the look in cute sandals.

Fit & Features
- Three-pack anklet set
- Two dainty chain link anklets
- One chain anklet with seashell charm
- Each has a lobster clasp closure
Style Number/Barcode: 07003-0554

Category Name: Vacation Looks

Price: $4.97 $10.90

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