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.

Girl On The Go Square Sunglasses
Made for the girl on the go. These square-frame sunglasses bring effortless cool to every outfit, whether you're brunch-bound or dodging exes at the beach party.

Fit & Features
- Square frames
- Tinted lenses
- 100% UV protection
Style Number/Barcode: 07008-000047

Category Name: Vacation Looks

Price: $10.90

Availability: Out of Stock
Product Badge:
- Ships Free
Sunday's Match Striped Wide Leg Pants
Sunday has met its perfect match! Slip-on these trendy striped pants for brunches with friends. It features an elasticized waistband, wide-leg silhouette, on linen fabric with lining and no stretch. Complete the look in the matching top.

Shop The Matching Top: Sunday's Match Striped Linen Top

Fit & Features
- Elasticized waistband
- Wide-leg silhouette
- Striped pattern
- Linen fabric, lined, no stretch
- Fits true to size
Style Number/Barcode: 06302-0620

Category Name: Vacation Looks

Price: $6.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Pom Perfect Round Straw Crossbody
You'll be ready for a summer picnic with this perfect straw crossbody featuring a round silhouette, top handle, attached shoulder strap, multi-colored pom poms on the front, and a zipper closure. Complete the look in a cute matching set.

Fit & Features
- Round silhouette
- Top handle
- Attached shoulder strap
- Multi-colored pom poms
- Top zipper closure
- Spacious interior with pocket
- Woven straw material
Style Number/Barcode: 07203-0979

Category Name: Vacation Looks

Price: $13.97 $28.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Glam Stud Rhinestone Bikini Top
Hey, glam stud! Flaunt your shine in this bikini top featuring a strapless, bandeau style with front rhinestone bars and smooth-lined knit fabric. Complete the look in the matching bikini bottoms for a Vegas pool party.

Shop Matching Bottoms: Glam Stud Rhinestone Bikini Bottoms

Fit & Features
- Strapless bandeau-style
- Front six rhinestone bars
- Smooth-lined knit fabric
- No padding
- Runs small, size up one size
Style Number/Barcode: 07104-0698

Category Name: Vacation Looks

Price: $10.97 $25.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Simple Glam Rhinestone Bikini Top
Simple and sultry, this trendy bikini top brings a subtle hint of glamour. It features a V-wired bust design and adjustable spaghetti straps with rhinestone detailing to add a stylish sparkle. Complete your poolside look with the matching bikini bottoms.

Shop Matching Bottoms: Simple Glam Rhinestone Bikini Bottoms

Fit & Features
- V-wired bust design
- Adjustable spaghetti straps, mini rhinestone embellishments
- Back metal bar closure
- No padding
- Moderate stretch
- Runs true to size
Style Number/Barcode: 07104-0699

Category Name: Vacation Looks

Price: $12.97 $28.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Style On Lock PVC Espadrille Wedges
Have your style on lock for the sunnier days ahead with these chic wedges featuring a square toe, dual PVC straps, and an espadrille sole. Complete the look in a flirty sundress.

Fit & Features
- Square toe
- PVC dual straps
- Espadrille sole
- Wedge style
- Runs true to size
Style Number/Barcode: 07406-0302

Category Name: Vacation Looks

Price: $12.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Slay The Trend High Rise Denim Shorts
Slay the denim trend in these flattering high-rise shorts featuring distressed accents, a v-cut silhouette, and a raw frayed hem on premium vintage-inspired medium wash denim fabric with cool color fading. Complete the look in a sultry bustier for a summer night out.

Fit & Features
- High-rise waist
- Distressed accents, v-cut silhouette
- Raw frayed hem
- Front button and hidden zipper closure
- Five-pocket styling, belt loop accents
- Medium wash denim, color fading, no stretch
- Fits true to size
Style Number/Barcode: 06603-0254

Category Name: Vacation Looks

Price: $6.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Who's That Girl Boho Maxi Skirt
Everyone will be asking who's that girl in this boho maxi skirt! Create a trendy free spirit vibe in this high-rise skirt featuring an elasticized waistband, flowy silhouette, and a sultry front slit on the maxi-length hem. Complete the look in a crochet crop top.

Fit & Features
- High-rise elasticized waist
- Flowy silhouette
- Front slit
- Maxi-length hem
- Boho paisley print
- Woven fabric, no stretch
- Fits true to size
Style Number/Barcode: 06301-0134

Category Name: Vacation Looks

Price: $6.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Chic Dainty Floral Tie-Front Top
This chic dainty floral printed top will elevate your weekend looks. It features long bishop sleeves with puff shoulders, a V-neckline with a tie-front design, and a majorly cropped hem. Style with high-rise denim and sleek hoop earrings.

Fit & Features
- Long bishop sleeves, puff shoulders, cinched hems
- V-neckline, tie-front
- Cropped fit
- Dainty floral print
- Woven fabric
- Runs true to size
Style Number/Barcode: 06003-1627

Category Name: Vacation Looks

Price: $6.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Sunny Day Floral Corset Top
A sunny day calls for this cute floral corset top! Featuring a sleeveless, sweetheart neck, wide straps, a built-in padded bust with underwire support, flexible boning inserts along the cropped bodice, and back hook-eye closures. Complete the look in jeans for a girl's day.

Fit & Features
- Sleeveless, sweetheart neck, wide straps
- Built-in padded bust, underwire support
- Flexible boning inserts
- Cropped hem
- Back hook-eye closures
- Floral woven fabric, no stretch, fits true to size
Style Number/Barcode: 06003-1829

Category Name: Vacation Looks

Price: $6.97 $38.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Island Palms Strappy Midi Dress
Enter paradise island in this sultry midi dress perfect for a dinner with a view! It features a sleeveless, square neck, spaghetti straps, high waist seam, and a strappy open-back, bodycon silhouette, side ruched seam, and slit along the hem. Complete the look in statement fringe earrings.

Fit & Features
- Sleeveless, square neck, spaghetti straps
- High waist seam, strappy open-back
- Bodycon silhouette
- Side ruched seam and slit
- Midi-length hem
- Palm print, knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4508

Category Name: Vacation Looks

Price: $9.97 $38.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Main Squeeze Striped Halter Wrap Top
One go in this halter top and it surely will be your main squeeze! It features a collared plunge V-neck, sultry open-back design, and a wrap tie-front cropped hem. Complete the look in high-rise jeans for a summer date night.

Fit & Features
- Sleeveless, collared plunge V-neck
- Halter bodice
- Open-back design
- Wrap tie-front
- Cropped hem
- Striped pattern, sweater knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1318

Category Name: Vacation Looks

Price: $11.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Effortless Style Sleeveless Romper
Get that effortless style that's perf for summer in this casual and cute sleeveless romper. It features tank shoulder straps, a deep V neck and back, a high waist with smocked detailing, trendy side cutouts, and flowy shorts. Pair this gauze romper with strappy sandals and hoop earrings.

Fit & Features
- Tank shoulder straps
- Deep V neck and back
- High waist, smocked detailing
- Side cutouts
- Flowy shorts
- Gauze fabric
- Runs true to size
Style Number/Barcode: 06303-0140

Category Name: Vacation Looks

Price: $6.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Summer Sunset Halter Bodysuit
Style up this trendy bodysuit for drinks at sunset with the girls! It features a sleeveless cross-front halter neckline, an alluring keyhole cutout at the bust, a thong bottom, and an all-over tropical palm leaf print. Pair this bodysuit with a high-rise mini skirt and mules.

Fit & Features
- Sleeveless cross front halter neckline, spaghetti straps
- Keyhole cutout at the bust
- Cross-back strap design
- Thong bottom, dual snap button closure
- Form-hugging fit
- Tropical palm leaf print
- Lined knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06001-4286

Category Name: Vacation Looks

Price: $6.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Feeling Breezy Crochet Bolero Sweater
Layer on this crochet bolero sweater for an effortlessly breezy, cute look!

Fit & Features
- Sheer crochet fabric
- Long sleeves with flare cuffs
- Open front design
- Ultra-cropped hem
- Runs true to size
Style Number/Barcode: 06005-000051

Category Name: Vacation Looks

Price: $12.97 $29.90

On Sale: Yes

Availability: In Stock

Available Color: TAN

Available Size: L
Trendy Ribbed Knit Cropped Tank
Elevate your casual summer 'fits with this trendy cropped tank! It features a sleeveless scoop neckline with a notched front design, tank shoulder straps, a center cutout at the hem, and a cropped, form-hugging fit. The lightweight ribbed knit fabric offers plenty of stretch. Style this tank with distressed denim shorts.

Fit & Features
- Sleeveless scoop neckline
- Notched front design
- Tank shoulder straps
- Center cutout at the hem
- Cropped, form-hugging fit
- Ribbed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 06002-1299

Category Name: Vacation Looks

Price: $6.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
All About Basic Slit Tank Top
Start with the basics. This sleeveless tank top is essential for building the perfect wardrobe! Featuring a square neck, wide straps, a form-fitting design, and trendy side slit accents along the cropped hem. Complete the look in high-rise jeans and sandals.

Fit & Features
- Sleeveless, square neck, wide straps
- Form-fitting design
- Side slit accents
- Cropped hem
- Double-layered modal fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06001-4367

Category Name: Vacation Looks

Price: $6.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Back Beauty Linen Halter Skater Dress
They'll love to watch you leave in this gorgeous skater dress featuring a sleeveless, halter neck with tie closure, and a smocked bodice that leads to a flowy, skater short silhouette with an open back and lattice bar accents. Complete the look in sleek hoop earrings for a day date.

Fit & Features
- Sleeveless, halter neck, tie closure
- Smocked bodice
- Flowy skater silhouette
- Short-length hem
- Open-back, lattice bar accents
- Linen fabric, lining, no stretch
- Fits true to size
Style Number/Barcode: 05102-4404

Category Name: Vacation Looks

Price: $6.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Island Flower Lattice Tank Top
Look prettier than the island flowers in this tropical floral tank top featuring a sleeveless V-neck, spaghetti straps, and a lattice front trim on a cropped hem. Complete the look in the matching skirt and sandals.

Shop Matching Skirt: Island Flower High Slit Midi Skirt

Fit & Features
- Sleeveless, V-neck, spaghetti straps
- Lattice front trim
- Cropped hem
- Tropical floral print
- Stretchy knit-lined fabric
- Runs true to size
Style Number/Barcode: 06001-4015

Category Name: Vacation Looks

Price: $6.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Cool Girl Chain-Detail Sunglasses
Bring cool-girl vibes to your look with these trendy shades! The sunglasses feature a plastic frame, rectangular-shaped tinted lenses, and chain-link detailing on the arms. Style with a faux leather shoulder bag.

Fit & Features
- Plastic frame
- Rectangular-shaped tinted lenses
- Chain-link detailing on the arms
- 100% UV protection
Style Number/Barcode: 07008-0975

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sleek Summer Vibes Swim Tank
Showcase sleek summer vibes in this chic swim tank! It features a scoop neckline, adjustable spaghetti straps, a small slit cutout under the bust, and an elastic banded hem. Complete your poolside look with the matching swim bottoms.

Shop Matching Bottoms: Sleek Summer Vibes Swim Bottoms

Fit & Features
- Scoop neckline
- Adjustable spaghetti straps
- Small slit cutout under the bust
- Elastic banded hem
- Metallic sheen
- Moderate stretch
- Runs true to size
Style Number/Barcode: 07104-0648

Category Name: Vacation Looks

Price: $4.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Willa Flocked Velvet Party Dress
Special Occasion

Create an enchanting vibe in the flowy Willa flocked velvet party dress. She features a sleeveless square neckline, spaghetti straps that lead to a lace-up back design for a customized fit, a high waistband, and a short party skirt with a chic fit and flare silhouette. The lined mesh fabric showcases an all-over floral flocked velvet design. Complete the look with block heels and a sparkly clutch.

Fit & Features
- Sleeveless square neckline, spaghetti straps
- Adhesive bra recommended
- Lace-up back design, tie closure, zipper, hook and eye closure
- High waistband, short party skirt, fit and flare silhouette
- Sheer mesh fabric, floral flocked velvet design, full knit lining
- Flowy fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05001-0989

Category Name: Vacation Looks

Price: $14.97 $49.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Effortlessly Stylish Halter Romper
Effortlessly stylish will be your vibe in this lightweight gauze romper! It features a sleeveless V-neckline, halter spaghetti straps, an open back with a tie detail, a high waist, and flowy, relaxed-fitting shorts. Complete the look with cute strappy sandals.

Fit & Features
- Sleeveless V-neckline
- Halter spaghetti straps, tie at the back of the neck
- Open back, tie detail
- High waist, side pockets
- Flowy, relaxed-fitting shorts
- Gauze fabric, no stretch
- Runs true to size
Style Number/Barcode: 06303-0116

Category Name: Vacation Looks

Price: $13.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Island Sun Strapless Jumpsuit
Feel the island sun on your shoulders in this tropical strapless jumpsuit featuring a tube-style bodice, side ruched seams, and a high-rise waist with hidden side pockets on the wide-leg silhouette. Complete the look in a floppy straw hat.

Fit & Features
- Strapless neckline
- Tube-style bodice, side ruched seams
- High-rise waist
- Hidden side pockets
- Wide-leg silhouette
- Tropical print, knit lined fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 06502-0852

Category Name: Vacation Looks

Price: $16.97 $39.90

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