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.

On Vacay Flower Strap Jelly Sandals
These cute jelly sandals say "I'm on vacay" with the thong strap design and pretty flower accent. The open back offers effortless on-and-off styling.

Fit & Features
- Jelly material
- Open almond-shaped toe
- Thong strap design
- Flower accent
- Open back, on-and-off styling
- Flat sole
- Runs true to size
Style Number/Barcode: 07404-000018

Category Name: Vacation Looks

Price: $9.97 $14.90

On Sale: Yes

Availability: In Stock

Available Color: MINT, NUDE

Available Size: 5, 6, 7, 8, 9, 10
Product Badge:
- Sale
The Vibe Rhinestone Star Clear Shield Sunglasses
Channel that iconic early 2000s vibe with these fabulous clear shield sunglasses! They feature a wide shield design with a flat top, sleek metal and plastic arms with trendy cutout detailing, mini rhinestones and star accents at each side, rubber nose pads, and clear lenses. Style with hoop earrings and a mini handbag.

Fit & Features
- Shield design with flat top
- Metal and plastic arms, cutout detail
- Mini rhinestones, star detail
- Metal nose bridge, rubber nose pads
- Clear lenses
- 100% UV protection
Style Number/Barcode: 07008-1078

Category Name: Vacation Looks

Price: $3.97 $12.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Drop It Low Rise Bootcut Denim Jeans
Pop, lock, and drop it down in these low-rise denim jeans to give your style a cute throwback vibe! They feature a hip-hugging fit, and a bootcut silhouette, and are composed of premium medium-wash denim with color fading and slight stretch. Complete the look in a flirty crop top and your favorite sneakers!

Fit & Features
- Low-rise waist
- Hip-hugging fit
- Bootcut silhouette
- Front button and hidden zipper closure
- Five-pocket styling, belt loop accents
- Premium medium wash denim, slight stretch, color fading
- Runs true to size
Style Number/Barcode: 06602-0440

Category Name: Vacation Looks

Price: $9.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Western Babe Cow Print Mini Skirt
Make the room say, "Yeehaw" looking like a sassy western babe! Create your perfect party outfit in this cow print mini skirt featuring a high-rise waist, bodycon fit, and a slit accent. The skirt is composed of french terry knit fabric with plenty of stretch. Complete the look with a faux leather bustier and accessories.

Fit & Features
- High-rise waist
- Bodycon silhouette
- Slit accent
- Mini-length hem
- Cow print
- Lined french terry knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06501-0697

Category Name: Vacation Looks

Price: $9.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Outside The Lines Floral Print Maxi Skirt
Style outside the lines and go for a bold chic look in this floral print maxi skirt. Style with the matching top for a complete look.

Shop Matching Top: Outside The Lines Floral Print Crop Top

Fit & Features
- Bold floral print, lined stretchy knit fabric
- High-rise waist
- Flowy maxi-length hem
- Runs true to size
Style Number/Barcode: 06501-1123

Category Name: Vacation Looks

Price: $36.90

Availability: Out of Stock
Product Badge:
- Ships Free
Throwback Babe Side Slit Mini Skort
Bring on the throwback vibes with this stylish mini skort! It's designed with a high-rise waist, front slit, and a hidden back zipper with a mini skirt overlay and shorts lining. Wear with a crop top to embrace the '90s look.

Fit & Features
- High-rise waist
- Back zipper closure
- Form-hugging, front slit
- Mini skirt overlay
- High-waist shorts
- Smooth woven fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06403-0188

Category Name: Vacation Looks

Price: $6.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Babe Alert Scoop Neck One-Piece Swimsuit
Fit & Features
- Smooth nylon-blend fabric with contrast trim, plenty of stretch
- Scoop neckline, adjustable spaghetti straps
- Low back
- High-cut design, cheeky bottom
- Form-hugging fit
- Runs true to size
- Returns are not accepted without the hygienic liner
Style Number/Barcode: 07105-0871

Category Name: Vacation Looks

Price: $14.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Fly With Me Butterfly Crochet Crop Top
You'll fly in this butterfly crochet crop top at festivals, concerts, and any kind of fun in the sun!

Fit & Features
- Crochet fabric
- Halter neckline, spaghetti strap ties
- Padded bra cups
- Butterfly design
- Open back with spaghetti strap tie
- Fitted crop hem
- Runs true to size
Style Number/Barcode: 06003-2758

Category Name: Vacation Looks

Price: $10.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
City Chic Ruffled Midi Dress
Step out like a scene straight out of a rom-com in a midi dress that gives major butterflies! The city-chic midi dress features a sleeveless square neckline, spaghetti straps that lead to a cross-strap design, and a high side slit on the left leg with a romantic ruffled trim. The relaxed fit waist leads to a midi-length A-line silhouette. The dress is composed of a smooth knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with mules.

Fit & Features
- Sleeveless square neckline
- Spaghetti straps, cross-back design
- Strapless bra friendly
- High side slit, ruffled trim
- Relaxed fit waist, A-line silhouette
- Midi-length hem
- Smooth knit fabric
- Form-hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05101-1038

Category Name: Vacation Looks

Price: $9.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Sultry Blossom Sweetheart Floral Mesh Mini Dress
Your amount of admirers will blossom when they see you in this sultry floral mesh mini dress! This flirty mini dress features a sweetheart neckline and padded bra cups for a flattering fit. Its adjustable spaghetti straps and ruched seams ensure the perfect bodycon silhouette. Complete the look in block heels.

Fit & Features
- Floral print, mesh fabric, sewn-in knit lining, moderate stretch
- Sweetheart neckline
- Adjustable spaghetti straps, padded bra cups
- Back zipper and hook-eye closure
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5478

Category Name: Vacation Looks

Price: $19.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Cool Meter Mid-Rise Parachute Cargo Pants
These parachute cargo pants have a high rating on the cool girl meter! They feature an elasticized mid-rise waist with side adjustable drawcords, side flap pockets with button closures, a loose-fit silhouette, and an adjustable drawcord hem. Style with a basic crop top for a movie night with friends!

Fit & Features
- Mid-rise elasticized waist, side adjustable drawcords
- Side flap pockets, button closures
- Loose-fit silhouette
- Adjustable drawcord hem
- Lightweight nylon woven fabric, no stretch
- Runs true to size
Style Number/Barcode: 06302-0745

Category Name: Vacation Looks

Price: $9.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
All Angles Metal Trim Square Sunglasses
Sleek and sculpted, these square sunglasses bring instant cool-girl energy. The metal-trimmed arms add just the right hint of shine—your new go-to for blocking shade in style.

Fit & Features
- Sleek square frames
- Tinted lenses
- Metal trim arms
- Rubber nose supports
- 100% UV protection
Style Number/Barcode: 07008-000084

Category Name: Vacation Looks

Price: $10.90

Availability: Out of Stock
Product Badge:
- Ships Free
High-Rise Destructed Boyfriend Jeans
Give your casually chic outfits an edgy aesthetic with these deconstructed high-rise jeans. These boyfriend-fit medium-wash denim jeans have the perfect amount of ripped detailing at the knees with a straight-leg silhouette for an absolutely on-trend look. Pair these high-waist ripped jeans with a cute crop top and chunky sneakers for day or a sparkly bustier with strappy heels for a sexy night look.

Fit & Features
- High-rise waist
- Boyfriend style leg
- Distressed detailing, slits at the knees
- Multi button-down front closure
- Five-pocket and belt loop design
- Medium wash denim fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06602-0184

Category Name: Vacation Looks

Price: $6.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
The Bottom Line High-Rise Parachute Cargo Pants
The bottom line? You need these cargo parachute pants to add to your weekly rotation! They feature a flattering high-rise waist with a back elastic band, a loose-fit leg silhouette, flap pockets, and an adjustable draw cord along the hem to get the perfect cinched look. Style with a basic crop top and sneakers for hanging out with friends!

Fit & Features
- High-rise waist, back elastic band
- Loose-leg silhouette
- Adjustable drawcord at the hem
- Four open front pockets, faux back pockets
- Hidden front hook and zipper closure, belt loop accents
- Lightweight nylon woven fabric, no stretch
- Runs true to size
Style Number/Barcode: 06302-0743

Category Name: Vacation Looks

Price: $6.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Flirt And Flutter Three-Pack Anklet Set
Flirt and flutter! This charming three-pack anklet set features two dainty anklets and one anklet with rhinestone trim and a butterfly charm. Each has a lobster clasp closure. Complete the look in a whimsical skater dress.

Fit & Features
- Three-pack anklet set
- Two dainty anklets
- One anklet with rhinestone trim and butterfly charm
- Each has a lobster clasp closure
Style Number/Barcode: 07003-0555

Category Name: Vacation Looks

Price: $2.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Of-The-Moment Chic Swirl Print Midi Dress
This of-the-moment chic swirl print midi dress is perf for happy hour! It features a sleeveless V-neckline, bungee spaghetti straps, a hip-hugging fit that flows out to a midi-length A-line silhouette, and a sultry front slit. The smooth jersey knit fabric showcases an alluring all-over swirl print pattern. Style with a faux leather blazer and strappy stilettos.

Fit & Features
- Sleeveless V-neckline
- Bungee spaghetti straps
- Hip-hugging fit, midi-length A-line silhouette
- Thigh-high front slit
- Swirl print pattern
- Jersey knit fabric, lined bust, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4817

Category Name: Vacation Looks

Price: $9.97 $38.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Radiate Romantic Vibes Strapless Floral Chiffon Maxi Dress
Radiate romantic vibes in this strapless floral chiffon maxi dress at garden parties or showers! The long ruffled silhouette adds flow and movement while the floral chiffon fabric adds a touch of femininity. Perfect for any occasion, this dress will make you stand out with its playful and flirty style! Complete the look with teardrop earrings.

Fit & Features
- Floral printed chiffon fabric with stretchy knit lining
- Strapless neckline
- Back zipper and hook-eye closure
- Ruffled flowy silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-3044

Category Name: Vacation Looks

Price: $9.97 $59.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Just Like A Dream Strappy Back Ruffled Maxi Dress
Make a jaw-dropping entrance in this gorgeous ruffled maxi dress at shower celebrations or on vacation! The flattering V-neckline draws the eye, while the intricate strappy back adorned with beaded insets creates an unforgettable exit view.

Fit & Features
- Airy woven gauze fabric, woven lining
- V-neckline
- Dual spaghetti straps
- Strappy back with beaded insets
- Cascading ruffles, flowy silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-6094

Category Name: Vacation Looks

Price: $9.97 $52.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Ready, Set, Slay Wrap Crop Denim Jacket
Ready to slay? Cause this denim jacket is your perfect pairing for trending all season! It features long sleeves, a lapel collar plunge neckline, and a wrap-tie cropped hem that lets you customize the style. Complete the look with matching bottoms.

Shop Matching Bottoms: Ready, Set, Slay V-Waist Denim Mini Skirt

Fit & Features
- Long sleeves
- Lapel collar plunge neckline
- Wrap-tie cropped hem
- Medium-wash denim fabric
- Moderate stretch
- Runs true to size
Style Number/Barcode: 06203-0505

Category Name: Vacation Looks

Price: $9.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
City Slicker High-Rise Faux Wrap Denim Skort
A perfect denim mini skort for a cute look in the city! Designed in a flattering high-rise wrap silhouette that gives it a contemporary touch.

Fit & Features
- Denim fabric, non-stretch
- High-rise waist dual button closures
- Faux wrap design
- Shorts bottom
- Mini-length
- Runs true to size
Style Number/Barcode: 06603-0441

Category Name: Vacation Looks

Price: $14.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Catch Flights Crochet Sweater Topper
She’s giving jet-setter vibes with just a touch of drama. Layer this crochet sweater topper over your fave tanks or dresses when your outfit needs a little extra flirt.

Fit & Features
- Sheer crochet knit fabric
- Long sleeves with flare cuffs
- Boat neckline
- Ultra-cropped hem
- Runs true to size
Style Number/Barcode: 06005-000105

Category Name: Vacation Looks

Price: $32.90

Availability: In Stock

Available Color: BLACK

Available Size: XS, S, M, L
Effortless And Breezy Short T-Shirt Dress
Style up this effortless and breezy short T-shirt dress for your casual weekend plans! It features a crew neckline, short sleeves, dual side pockets, a loose T-shirt fit, a short-length hem, and an A-line silhouette. The cotton-blend fabric has a moderate stretch. Pair with hoop earrings and strappy sandals.

Fit & Features
- Crew neckline
- Short sleeves
- Dual side pockets
- Loose T-shirt fit
- Short-length hem, A-line silhouette
- Cotton-blend fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5044

Category Name: Vacation Looks

Price: $8.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Walk The Line Crepe Geo Mini Dress
Walk the line into this artsy geometric print crepe dress to give your closet must needed prints! It features a sleeveless V-neckline, sleek bungee spaghetti straps, a bodycon silhouette, and a flirty slit along the mini-length hem. Complete the look in heeled sandals for a casual brunch downtown!

Fit & Features
- Sleeveless V-neckline
- Bungee spaghetti straps
- Bodycon silhouette
- Front slit, mini-length hem
- Geometric print
- Stretchy crepe fabric
- Runs true to size
Style Number/Barcode: 05102-4849

Category Name: Vacation Looks

Price: $6.97 $33.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Chic Faux Leather Mini Bag
Carry your essentials in this chic faux leather mini bag to adorn your OOTD! Features a top handle with a scrunched design, a snap-button closure, and a spacious lined interior. Complete the look with a sleek necklace and earrings.

Fit & Features
- Faux leather material
- Top handle
- Mini scrunched design
- Snap-button closure
- Spacious lined interior
Style Number/Barcode: 07201-0136

Category Name: Vacation Looks

Price: $9.97 $24.90

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