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.

Vineyard Chic Cork Lace-Up Heels
Grab the girls and these cork block heels for a day-out wine tasting! They feature an almond toe, braid toe strap, and a lace-up tie closure. Complete the look in a breezy jumpsuit.

Fit & Features
- Almond toe
- Block heel
- Braid toe strap
- Lace-up tie closure
- Runs true to size
Style Number/Barcode: 07401-4080

Category Name: Vacation Looks

Price: $5.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Aloha Babe Flower Graphic Crop Tee
Whether you're on vacay or just hanging out, this flower graphic crop tee adds a cute look to your favorite bottoms.

Fit & Features
- Cotton knit stretchy fabric
- Short sleeves
- Crew neckline
- Flower graphic
- Relaxed fit
- Crop hem
- Runs true to size
Style Number/Barcode: 06002-000051

Category Name: Vacation Looks

Price: $6.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Summer Glow Rhine Layered Choker
Unleash your summer glow and adorn your outfit with this choker necklace featuring a three-layered design, one rhinestone row, one snake chain row, one chainlink row, and a lobster clasp closure. Complete the look in a denim romper.

Fit & Features
- Three-layered design choker
- One rhinestone row
- One snake chain row
- One chainlink row
- Lobster clasp closure
Style Number/Barcode: 07002-1239

Category Name: Vacation Looks

Price: $5.97 $12.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Take Note V-Neck Sweater Dress
Everyone will take note of how sultry this sweater dress is on you! It features a sleeveless, v-neck, cutout bodice with wrap tie-back closure, side slit accent, and a midi, curve-hugging silhouette. Complete the look in chic strappy heels for a daytime soiree.

Shop More Styles: The Sweater Collection

Fit & Features
- Sleeveless, v-neck, tank-style straps
- Cutout bodice
- Wrap tie-back closure
- Side slit accent
- Midi, curve-hugging silhouette
- Sweater rib-knit fabric
- Fits true to size
Style Number/Barcode: 06005-1488

Category Name: Vacation Looks

Price: $6.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Make It Chic Tube Top
This strapless tube top moment hugs you just right with ruched details for that elevated off-duty model look.

Fit & Features
- Smooth knit fabric with subtle sheen
- Strapless tube folded neckline
- Ruched details
- Fitted hem
- Runs true to size
Style Number/Barcode: 06001-000230

Category Name: Vacation Looks

Price: $24.90

Availability: Out of Stock
Product Badge:
- Ships Free
Always Trendy Lace-Up Tank Top
Always trendy and a staple! This sleeveless tank top adds the perfect eye-catching style to your everyday fit. It features a V-neck, thin shoulder straps, and a trio of lace-up plackets along the cropped hem on stretchy, rib-knit fabric. Complete the look in flare pants for a summer carnival.

Fit & Features
- Sleeveless, V-neck, thin shoulder straps
- Three lace-up plackets
- Cropped hem
- Stretchy rib-knit fabric
- Runs true to size
Style Number/Barcode: 06002-1339

Category Name: Vacation Looks

Price: $10.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Biker Babe Cropped Graphic Tee
Bring the cool girl energy with this edgy graphic tee! It features a crew neckline, short sleeves, a center motorcycle graphic with the script "American Motorcycle Legend," front slashed detailing, and a cropped, form-hugging fit. Style with high-rise distressed denim.

Fit & Features
- Crew neckline, short sleeves
- Motorcycle graphic
- Script that reads "American Motorcycle Legend"
- Front slashed detailing
- Cropped, form-hugging fit
- Cotton fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06002-1288

Category Name: Vacation Looks

Price: $6.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Glitzy Metallic Bow Sandals
Bring the glitz and glamour with these dressy metallic slide-on sandals. They feature an open square-shaped toe, a wide pleated toe strap with a bow accent, and a flat sole. Style with a wide-leg jumpsuit and a clutch.

Fit & Features
- Open square-shaped toe
- Wide pleated toe strap
- Bow accent
- Flat sole
- Metallic finish
- Faux leather material
- Runs true to size
Style Number/Barcode: 07404-1075

Category Name: Vacation Looks

Price: $14.97 $20.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Perfect Swirls V-Neck Mini Dress
Perfectly swirled and smoothed to perfection! Showcase a head-turning look in this sleeveless mini dress featuring a v-neck, bungee spaghetti straps, bodycon silhouette, slit accent, and a marble print on brushed knit fabric. Complete the look in lace-up heels for a summer party.

Fit & Features
- Sleeveless, v-neck, bungee spaghetti straps
- Bodycon silhouette
- Slit accent
- Mini-length hem
- Marble print
- Brushed knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4660

Category Name: Vacation Looks

Price: $9.97 $33.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Speedster Racing Graphic Crop Top
Show off your need for speed with a graphic crop top that brings the heat! The top features a crew neckline, short sleeves, an asymmetrical slit paired with safety pins, and an image of a racecar with "Speed Racing" text above the car. The crop top is composed of a cotton knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with pleather shorts and combat booties for an edgy outfit.

Fit & Features
- Crew neckline
- Short sleeves
- Asymmetrical slit, safety pins
- Racecar image, "Speed Racer" text
- Cropped hem
- Cotton knit fabric
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 06002-1397

Category Name: Vacation Looks

Price: $9.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Real Cute Off The Shoulder Top
You'll look real cute showing some shoulder. This crop top features long sleeves, a halter tie neckline, an off-the-shoulder bodice, and a front ruched design on soft and stretchy knit fabric. Complete the look in a midi skirt and sandals.

Fit & Features
- Long sleeves
- Halter tie neckline
- Off-the-shoulder bodice
- Front ruched design
- Cropped hem
- Soft and stretchy knit fabric
- Fits true to size
Style Number/Barcode: 06001-4387

Category Name: Vacation Looks

Price: $9.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Sleek Basic One-Shoulder Crop Top
This sleek basic crop top will step up your everyday style. It features a sleeveless one-shoulder neckline with an asymmetrical tank strap, a cropped, form-hugging fit, and is composed of a stretchy ribbed sweater knit fabric. Pair this top with cutoff denim shorts and slides.

Fit & Features
- Sleeveless one-shoulder neckline
- Asymmetrical tank strap
- Cropped, form-hugging fit
- Ribbed sweater knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1506

Category Name: Vacation Looks

Price: $6.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Mid Rise Straight Leg Denim Jeans
Kick your street style up a notch in these denim jeans featuring a flattering mid-rise asymmetrical waist, straight-leg silhouette, and vintage-inspired medium wash denim fabric with a light color fading. Complete the look with a crop top and mules.

Fit & Features
- Mid-rise asymmetrical waist
- Straight-leg silhouette
- Five-button fly closures
- Belt loop accents
- Five-pocket styling
- Medium wash non-stretch denim, light color fade
- Runs small, please size up
Style Number/Barcode: 06602-0386

Category Name: Vacation Looks

Price: $6.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Desert Explorer Graphic Crop Top
Step up your rocker-chic look with this cool graphic crop top. It features a sleeveless halter neckline with a sleek O-ring accent and chain-link straps, a center eagle and desert background graphic with the script "Desert Explorer, Feel The Sunset," and a cropped, form-hugging fit. Style with distressed denim and combat boots.

Fit & Features
- Sleeveless halter neckline
- O-ring accent, chain-link straps, adjustable lobster clasp closure
- Eagle and desert background graphic
- Script that reads "Desert Explorer, Feel The Sunset"
- Cropped, form-hugging fit
- Cotton-blend fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06002-1375

Category Name: Vacation Looks

Price: $6.97 $21.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Stay Glam Crochet Handbag
Keep your summer look oh-so-glam with this glitzy crochet handbag. It features a tote design with wooden O-ring handles and an included sequin embroidered pouch to store all your essentials in. Style with a mini dress and espadrille sandals.

Fit & Features
- Crochet bag
- Tote design
- Wooden O-ring handles
- Sequin embroidered pouch, top zipper closure
Style Number/Barcode: 07203-1088

Category Name: Vacation Looks

Price: $8.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
She Came to Slay Floral Corset Tube Top
When your outfit speaks before you do. This abstract floral tube top brings the drama with corset vibes and a flawless, sculpted fit made for rooftop nights and flirty first dates.

Shop Matching Bottoms: She Came to Slay Floral Maxi Skirt

Fit & Features
- Sheer mesh fabric with knit lining, high stretch
- Abstract floral print
- Strapless straight-across neckline
- Flexible boning
- Back hook-eye closures
- Fitted, curved, mid-length hem
- Runs true to size
Style Number/Barcode: 06001-000142

Category Name: Vacation Looks

Price: $6.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Sunset Beauty Cutout Midi Skirt
Showcase your beauty on a sunset stroll in this alluring midi skirt. It features a high-rise waist with a strappy cutout design, a midi-length, curve-hugging fit, and a chic side slit accent. Style with the matching crop top for the perfect look.

Shop Matching Top: Sunset Beauty Halter Crop Top

Fit & Features
- High-rise waist, strappy cutout design
- Midi-length hem, form-fitting silhouette
- Side slit
- Sweater knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06501-0714

Category Name: Vacation Looks

Price: $6.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Sunset Beauty Halter Crop Top
Showcase your beauty on a sunset stroll in this alluring crop top. It features an off-the-shoulder neckline with short fitted sleeves and thin halter straps, a cinched accent at the bust, a tie-back design, and a cropped, form-hugging fit. Style with the matching midi skirt for the perfect look.

Shop Matching Bottoms: Sunset Beauty Cutout Midi Skirt

Fit & Features
- Off-the-shoulder neckline
- Short fitted sleeves, thin halter straps
- Cinched accent at the bust
- Tie-back design
- Cropped, form-hugging fit
- Sweater knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1594

Category Name: Vacation Looks

Price: $6.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Options Open O-Ring Midi Dress
Keep your options open and wear this dress for your weekend plans! It features a sleeveless, v-neck, spaghetti straps, an open-back with an o-ring insert, a bodycon silhouette, and a midi hem on stretchy rib-knit fabric. Complete the look with chic heels.

Fit & Features
- Sleeveless, v-neck, spaghetti straps
- Open-back, o-ring insert
- Bodycon silhouette
- Midi hem
- Stretchy rib-knit fabric
- Fits true to size
Style Number/Barcode: 05102-4659

Category Name: Vacation Looks

Price: $9.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sultry Bloom Floral Mesh Maxi Skirt
Serve a sultry vibe in this blooming floral printed mesh maxi skirt! Designed with ruched side seams to show off your curves, style with the matching tube top for a gorgeous look.

Shop Matching Top: Sultry Bloom Floral Mesh Tube Top

Fit & Features
- Sheer mesh fabric with full-length knit lining, high stretch
- Floral print
- High-rise waist
- Maxi-length hem, lettuce-edge trim
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06501-1142

Category Name: Vacation Looks

Price: $10.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Feeling Flawless Halter Jumpsuit
You'll look and feel flawless in this vacay-worthy halter jumpsuit featuring a sleeveless, ruched bodice with keyhole cutouts, a tie-neck closure, a partial open-back, and a wide-leg silhouette. Complete the look in wedges for a sunset dinner.

Fit & Features
- Sleeveless, halter neck, tie closure
- Keyhole cutouts
- Ruched bodice
- Partial open-back design
- Wide-leg silhouette
- Stretchy knit fabric
- Fits true to size
Style Number/Barcode: 06502-1152

Category Name: Vacation Looks

Price: $6.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Effortless Muse Chiffon Skater Dress
Showcase your effortless beauty in this airy chiffon skater dress. It features a sweetheart neckline with ruffled trim and a pleated bust, long bishop sleeves, a fitted high waistband, and a tiered skater skirt with a short hem and a fit and flare silhouette. Style this skater dress with your fave mules.

Fit & Features
- Sweetheart neckline, ruffled trim, pleated bust
- Long sheer bishop sleeves, cinched hems
- Smocked back design, fitted high waistband
- Fit and flare silhouette
- Tiered skater short-length skirt
- Chiffon fabric fabric, woven lining, no stretch
- Runs true to size
Style Number/Barcode: 05101-1650

Category Name: Vacation Looks

Price: $9.97 $52.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Sleek Sleeveless Faux Leather Corset
Step up your night out 'fit with this sleek sleeveless faux leather corset. It features a V-neckline, tank shoulder straps, a partially open back with lower hook and eye closures, a corset-designed front with an asymmetrical cropped hem, and a form-hugging fit. Style with a mini skirt and heels.

Fit & Features
- Sleeveless V-neckline
- Tank shoulder straps
- Open back, lower hook and eye closures
- Corset-designed front, asymmetrical cropped hem
- Form-hugging fit
- Faux leather fabric
- Runs true to size
Style Number/Barcode: 06003-1957

Category Name: Vacation Looks

Price: $6.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Summer Fling Twist Front Crop Top
So much for a summer fling! With this crop top, you're sure to fall for it over and over again. It features a sleeveless, sweetheart neck, criss-cross back straps, and a twisted front on lined knit fabric. Complete your look with the matching bottoms.

Shop Matching Bottoms: Summer Fling Twist Slit Maxi Skirt

Fit & Features
- Sleeveless, sweetheart neck, spaghetti straps
- Criss-cross back straps
- Twisted front
- Cropped hem
- Lined knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06001-4374

Category Name: Vacation Looks

Price: $6.97 $16.90

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