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.

Floral Flirt Skater Dress
Hey bby! You'll be a total flirt in this pretty floral skater dress! Pair with some strappy sandals and a boho chic panama hat!

Fit & Features
- Spaghetti straps | V neck and back
- Ruched front | Tie closure
- Small front keyhole cut out
- High waist
- Flowy skater skirt
- Stretchy knit fabric
- Small all over floral print
Style Number/Barcode: 05102-0416

Category Name: Vacation Looks

Price: $13.97 $35.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Floral Tropical Surplice Wrap Maxi Dress
Wrap yourself in a floral maxi dress. Bring the vacation vibes this season in this dress that features an all-over tropical floral print, a sleeveless surplice wrap neckline, and spaghetti straps. The relaxed fit waist leads to a carefree maxi length silhouette. The dress is composed of a lightweight smooth knit fabric that offers a form hugging fit. Complete your outfit with dainty bracelets and face-framing sunglasses.

Fit & Features
- Sleeveless
- Wrap v-neckline
- Spaghetti straps
- Tropical floral print
- Maxi length silhouette
- Smooth knit fabric
- Form hugging fit
Model is 5'4" with 33" bust, 24.5" waist and 39" hips. She is wearing a size small.
Style Number/Barcode: 05102-0194

Category Name: Vacation Looks

Price: $21.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Tropical Print Cowl Neck Maxi Dress
Head to the tropics in a maxi dress. The vacation-worthy maxi dress features a draped cowl neck, spaghetti straps that lead to a bold open back and an all-over tropical palm leaf print. The relaxed fit waist leads to a sweeping maxi length silhouette that is accented with a daring high slit. Complete your look with clear heels to let the print speak for itself and a floppy hat.

Fit & Features
- Cowl neck
- Spaghetti straps
- Open back
- High slit, maxi length silhouette
- Tropical palm leaf print
- Smooth knit fabric
- Form hugging fit, moderate stretch
Model is 5'4" with 33" bust, 24.5" waist and 39" hips. She is wearing a size small.
Style Number/Barcode: 05101-0446

Category Name: Vacation Looks

Price: $9.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Pretty In Plaid Mini Dress
Keep it pretty in plaid with this brunch ready mini dress! This season-ready dress only needs a pair of wedges and a pop of jewel tones for a complete look!

Fit & Features
- Square Neckline
- 3/4 Puff Sleeves
- Plaid Print
- Lined Lightweight Fabric
- Mini Length Silhouette
- Relaxed Fit
- Minimal Stretch
Style Number/Barcode: 05102-0680

Category Name: Vacation Looks

Price: $9.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Wrapped In Rhinestones Wrap Sandals
Get wrapped in rhinestone sandals to create a glam vibe for your best outfits. These sandals feature a rhinestone embellished band and a matching rhinestone embellished wrap around strap. Complete your look with high waist shorts and a glam bustier.

Fit & Features
- Single rhinestone embellished strap
- Wrap around rhinestone strap
- Flat footbed
Style Number/Barcode: 07404-0662

Category Name: Vacation Looks

Price: $12.97 $20.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
One Band Faux Nubuck Slides
Step out in stylish slides to complete all your best outfits this season. These slides feature an open toe with a single wideband and easy slip-on design. Keep it casual in high waist shorts and a smocked top.

Fit & Features
- Flat footbed
- Open toe with a single wide strap
- Faux nubuck material
Style Number/Barcode: 07404-0298

Category Name: Vacation Looks

Price: $12.97

Availability: Out of Stock
Product Badge:
- Sale
Clear PVC Rhinestone Slides
Keep it simply studded in rhinestone slides this season. These dazzling slides feature a wide clear PVC band, rhinestone embellishments, and a metallic flat footbed. Complete your look with a fab romper or gorgeous in a flowy maxi dress.

Fit & Features
- Clear PVC strap
- Rhinestone embellishments
- Metallic footbed
Style Number/Barcode: 07404-0526

Category Name: Vacation Looks

Price: $10.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Keep it Basic Face Mask
Stay safe in this solid face mask that won’t clash with your 'fit! It features a soft woven fabric with comfortable ear loops. Complete the look with a cute crossbody purse.

Fit & Features
- Woven fabric
- Ear loops
- This is not a medical-grade mask nor is a substitute for medical-grade equipment
- Wash before and after use is recommended
- Please consult local health authority for guidance on the use of non-medical grade masks
Face masks are final sale merchandise and may not be returned or exchanged.
Style Number/Barcode: 07305-0107

Category Name: Vacation Looks

Price: $1.97 $6.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Floral Moment Maxi Dress
Create a charming moment in florals in this sweet maxi dress! Perfect for brunch when paired with fab heels and a neutral handbag!

Fit & Features
- Wrap V-Neckline
- Spaghetti Straps
- Elastic Waist
- Floral Print
- Maxi Silhouette
- Lined Knit Fabric | Mini Skirt Length Lining
- Relaxed Fit | Moderate Stretch
Style Number/Barcode: 05101-0530

Category Name: Vacation Looks

Price: $14.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Ditsy Print Smocked Peplum Tube Top
Spring into florals in this cute top. Head out for a coffee date in this fab top that features a charming floral ditsy print, a smocked bodice for a comfortable fit and a flirty peplum hem. Complete look with dainty hoop earrings and high waist jeans.

Fit & Features
- Sleeveless square neckline
- Smocked bodice
- Ditsy floral print
- Peplum hem
- Relaxed fit
- Moderate stretch
Model is 5'8" with a 34" bust, 24" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 06003-0792

Category Name: Vacation Looks

Price: $6.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Floral Fusion Chiffon High Low Top
Bring a burst of florals in a fab top. Bring the charm for your next date night or brunch with the squad in this sweeping floral top that features a plunging v-neckline with button closure, a trendy high-low hem, and is composed of an airy chiffon fabric. Complete your look with light wash denim jeans and clear heels.

Fit & Features
- Plunging v-neckline with button closure
- Short flutter sleeves
- Floral print
- High-low hem
- Chiffon fabric
Model is 5'8" with a 34" bust, 24" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 06003-0546

Category Name: Vacation Looks

Price: $9.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Floral Moment Asymmetrical High Slit Midi Dress
Make a fab impression in a floral dress, perfect for a first date. The midi dress features a gorgeous floral print, a wrap V-neckline for a flattering fit, and an asymmetrical high slit. Complete your look with strappy heels and hoop earrings to complement this fab print.

Fit & Features
- Sleeveless, v-neck, spaghetti straps
- Bodycon silhouette
- Asymmetrical high slit
- Midi-length hem
- Floral print, knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-0562

Category Name: Vacation Looks

Price: $9.97 $35.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Zipper Key Hole Ribbed Knit Mini Dress
This ribbed mini dress features a zippered keyhole that adds an element of sexiness! We love to see you pairing this look with some booties or heels!

Fits & Features
- Ribbed Crew Neck
- Front Zipper Opens To Keyhole Cut Out
- Mini Length Silhouette
- Ribbed Fabric
- Form Hugging Fit I Plenty Of Stretch
Style Number/Barcode: 05102-0574

Category Name: Vacation Looks

Price: $10.97 $28.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Always Sweet Ruffled Eyelet Lace Mini Dress
Make your sweet impression in this eyelet lace mini dress detailed with ruffled straps and an adorable ruched neckline. The form-hugging fit will highlight your stunning curves.

Fit & Features
- Eyelet lace fabric lined with stretchy knit
- Sweetheart neckline, ruching
- Ruffled straps
- Mini-length form-hugging silhouette
- Runs true to size
Style Number/Barcode: 05102-6002

Category Name: Vacation Looks

Price: $7.97 $39.90

On Sale: Yes

Availability: In Stock

Available Color: WHITE

Available Size: M, L
Product Badge:
- Sale
Feline Fine Cat Eye Sunglasses
Stun on them all in cat-eye sunglasses! Keep your vacation look on point with a pair of cat-eye sunglasses that feature a flat top and dark tinted lenses that go with everything. Complete your look with a floral maxi dress or fab matching separates.

Fit & Features
- Cat-eye frame
- Hard plastic frame
- Dark-tinted lenses
Style Number/Barcode: 07008-0787

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Double Band Lucite Block Heels
Cleary stay on trend in lucite heels this season. The heels feature a double row of clear straps and a lucite block heel. Complete your look with floral matching separates or a flowy sundress.

Fit & Features
- Open almond toe
- A double row of clear PVC straps
- Lucite narrow block heel
- Narrow platform
Style Number/Barcode: 07401-2216

Category Name: Vacation Looks

Price: $12.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Tie Front Star Print Crop Top
Stand out in this star print top that is perfect for all your dreamy looks. This top features a plunging v-neckline with tie front ties, a cropped hem, and a star print design. Complete your look with high waist shorts and hoop earrings.

Fit & Features
- Plunging v-neckline
- Tie front bodice
- Short sleeves
- Star print
- Cropped hem
Model is 5'6" with 31" bust, 26" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06204-0632

Category Name: Vacation Looks

Price: $9.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sleeveless Dotted Wide Leg Jumpsuit
Keep it darling in a dotted jumpsuit. This charming jumpsuit is perfect for your next bridal shower or grabbing drinks for Sunday brunch. The jumpsuit features an elastic sleeveless square neckline for a comfortable no-slip fit, a pretty swiss dot pattern throughout, and flowy wide-leg pants. Complete look with sunglasses and wedges.

Fit & Features
- Sleeveless square neckline
- Drawstring tie waist
- Wide leg pants
- Swiss dot pattern
- Short length lining
- Relaxed fit
Model is 5'8" with a 34" bust, 24" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 06402-0262

Category Name: Vacation Looks

Price: $6.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Tie Dye Twist Front Bell Sleeve Crop Top
Keep it trendy in a tie-dye crop top. Perfect for creating groovy vibes for a festival outfit this crop features a tie-dye print, a twist front bodice, and flowy bell sleeves. Complete this fab top with high waist shorts and fringe earrings.

Fit & Features
- Plunging v-neckline
- Twist-front bodice
- Tie-dye print
- Long bell sleeves
Model is 5'8" with a 34" bust, 24" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 06001-2566

Category Name: Vacation Looks

Price: $8.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Tropical Floral Sleeveless Wide Leg Jumpsuit
Bring a tropical vibe in a floral jumpsuit this season. Throw on this jumpsuit for that vacation getaway. The jumpsuit features a vibrant floral print, ruched side seams, and a flowy wide leg pant. Complete your look with sunglasses and wedges.

Fit & Features
- Sleeveless square neckline
- Ruched side seams at the bodice
- Floral print
- Flowy wide leg pant
- Smooth knit fabric
- Form hugging fit, moderate stretch
Model is 5'8" with a 34" bust, 24" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 06502-0386

Category Name: Vacation Looks

Price: $13.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Floral Bliss Smocked Mini Dress
Bring out the floral prints and wave those gloomy winter-blues goodbye! Radiate that early springtime energy in this cute mini dress!

Fits & Features
- Adjustable Spaghetti Straps
- Lettuce Edge Trim At Square Neckline & Hem
- Smocking Throughout
- Mini Length Silhouette
- Curve Hugging Fit
- Ample Stretch
Style Number/Barcode: 05102-0519

Category Name: Vacation Looks

Price: $19.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Crochet Lace Fringe Cover Up
Cover up in crochet lace when relaxing poolside this season. This must-have cover-up features a crochet lace throughout and a fringed hem. Complete your look with a trendy bikini and wedges.

Fit & Features
- Crochet lace
- Fringed hem
- Unlined
Style Number/Barcode: 07305-0077

Category Name: Vacation Looks

Price: $5.97 $12.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
High Waist Destructed Cut Off Shorts
Kick-off summer in cut off shorts. These light wash shorts are what you need for days spent poolside or on vacation. The shorts feature a high rise waist, a single button with zipper closure, a traditional five-pocket with belt loop design, and a cut-off hem with frayed detailing. The shorts are composed of a light wash denim fabric that offers a relaxed fit. Complete your look with a graphic tee and dad sneakers to rock a casual laid back vibe.

Fit & Features
- High rise waist
- Single-button with zipper closure
- Traditional five-pocket with belt loops
- Light wash denim
- Relaxed fit
Model is 5'8" with a 34" bust, 24" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 06603-0121

Category Name: Vacation Looks

Price: $6.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Pleated Glitter Sarong Wrap
Bring the glow in a glitter sarong wrap. This glam sarong wrap is composed of a lightweight pleated fabric adorned with glitter throughout. Complete your summertime look with a head-turning swimsuit and heels.

Fit & Features
- Traditional sarong-wrap design
- Lightweight pleated fabric
- Glitter
Style Number/Barcode: 07305-0089

Category Name: Vacation Looks

Price: $6.97 $14.90

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