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.

Downtown Nights Wide-Leg Pants
Stroll downtown tonight in these breezy wide-leg pants featuring a high-rise waist, hidden side pockets, and pleats going down the front on woven fabric with minimal stretch. Complete the look in a one-shoulder top and mules.

Fit & Features
- High-rise waist
- Hidden side pockets
- Pleats down the front
- Wide-leg silhouette
- Pull-on/off styling
- Woven fabric, minimal stretch
- Fits true to size
Style Number/Barcode: 06402-0526

Category Name: Vacation Looks

Price: $6.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Elevated Basic Sweater Knit Bodysuit
Step up your look with this elevated basic bodysuit! Featuring a sleeveless crew neckline, an asymmetrical cutout above the bust, and a form-hugging fit, you can effortlessly transition this bodysuit from day to night. Style with high-rise denim and heeled booties for every day, and faux leather pants and mules for nights out.

Fit & Features
- Sleeveless crew neckline
- Asymmetrical cutout above the bust
- Thong bottom, dual snap-button closure
- Ribbed sweater knit fabric
- Moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1550

Category Name: Vacation Looks

Price: $6.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Babe In Pointed Toe Boots
Walk tall babe in these PU pointed-toe boots featuring a stylish and sleek under-the-knee silhouette with a block heel and side zipper closure. Complete the look with a boyfriend blazer.

Fit & Features
- Pointed toe
- Block heel
- Side zipper closure
- Under-the-knee length
- PU material
- Runs true to size
Style Number/Barcode: 07402-0796

Category Name: Vacation Looks

Price: $12.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Knit Alone Mock Neck Top
Cute alone but better together! This rib-knit top features a sleeveless mock neckline and a cropped hem. Complete the look in the matching bottoms and clear strap heels.

Shop Matching Bottoms: Knit Alone Slit Maxi Skirt

Fit & Features
- Mock neckline
- Sleeveless
- Cropped hem
- Ribbed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 06001-4439

Category Name: Vacation Looks

Price: $9.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Knit Alone Slit Maxi Skirt
Cute alone but better together! This rib-knit maxi skirt features a high-rise waist, a curve-hugging silhouette, and an asymmetrical slit hem. Complete the look in the matching top and clear strap heels.

Shop Matching Top: Knit Alone Mock Neck Top

Fit & Features
- High-rise elasticized waist
- Curve-hugging silhouette
- Asymmetrical slit
- Maxi-length hem
- Ribbed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 06501-0685

Category Name: Vacation Looks

Price: $6.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Fell For You Knit Twist Bra Top
They'll fall for you in this knit bra top featuring a sleeveless V-neck, tank-style straps, a twisted bodice, and a cropped hem on sweater ribbed-knit fabric with minimal stretch. Complete the look in the matching cardigan.

Shop Matching Cardigan: Fell For You Knit Open Cardigan

Fit & Features
- Sleeveless, V-neck
- Tank-style straps
- Twisted bodice
- Cropped hem
- Sweater ribbed-knit fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06005-1409

Category Name: Vacation Looks

Price: $6.97 $21.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Angel Number Necklaces
Support, alignment, and protection. Let this angel number necklace be a positive reminder of aspects of everyday life. It features a dainty chain link with coin accents and numerical charms. Complete the look in a casual dress and your fave sneakers.

Fit & Features
- Dainty chain link
- Coin accents
- Numerical charms with meanings
- 222 alignment, 333 support, 444 protection
- Lobster clasp closure
Style Number/Barcode: 07002-1336

Category Name: Vacation Looks

Price: $3.97 $8.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
All The Class Crepe Wide Leg Pants
These crepe trouser pants have all the class your outfit needs for office hours to happy hour! They feature a high-rise waist with faux button accents, a wide-leg silhouette, and a pull-on/off styling. Complete the look in a blazer and heels.

Fit & Features
- High-rise waist
- Faux button accents
- Wide-leg silhouette
- Crepe knit fabric, moderate stretch
- Pull-on/off styling
- Fits true to size
Style Number/Barcode: 06502-1277

Category Name: Vacation Looks

Price: $6.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Walking Knit Style Block Booties
Take stylish steps in these block heel booties featuring an on-trend pointed toe, partial knit and faux leather material, and an above-the-ankle length. Complete the look in a chic blazer.

Fit & Features
- Pointed toe
- Block heel
- Above-the-ankle length
- Partial knit and faux leather material
- Pull-on/off styling
- Runs true to size
Style Number/Barcode: 07403-1611

Category Name: Vacation Looks

Price: $12.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Cadet Girl Cargo Mini Skirt
Command the room as the fashion cadet ready for duty in this cargo mini skirt featuring a high-rise waist, front button closure, belt loop accents, side flap pockets, and a bodycon silhouette. Complete the look in a cool graphic tee and boots.

Fit & Features
- High-rise waist
- Front button and hidden zipper closure
- Belt loop accents, side flap pockets
- Bodycon silhouette
- Mini-length hem
- Woven cotton fabric, slight stretch
- Runs true to size
Style Number/Barcode: 06301-0151

Category Name: Vacation Looks

Price: $6.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
So Sleek Zebra Print Midi Dress
Keep your look so sleek with a midi dress that levels up your casual outfits! It features a sleeveless V-neckline with a knot-front design, a small keyhole cutout under the bust, spaghetti straps, a midi-length, fitted, A-line sihouette, and a chic front slit. The smooth knit fabric features an all-over zebra print pattern. Stye with strappy mules.

Fit & Features
- Sleeveless V-neckline, knot-front design
- Keyhole cutout under the bust
- Spaghetti straps
- Midi-length hem, fitted A-line silhouette
- High front slit
- Knit fabric, plenty of stretch
- Zebra print
- Runs true to size
Style Number/Barcode: 05102-4703

Category Name: Vacation Looks

Price: $9.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Refresh Striped Sweater Dress
Refresh your closet in this striped sweater dress featuring a sleeveless, crew neckline, bodycon silhouette, and a mini-length hem on stretchy, rib-knit fabric. Complete your trendy look in statement heels.

Shop More Styles: The Sweater Collection

Fit & Features
- Sleeveless, crew neckline
- Bodycon silhouette
- Mini-length hem
- Striped pattern
- Stretchy rib-knit fabric
- Fits true to size
Style Number/Barcode: 06005-1485

Category Name: Vacation Looks

Price: $14.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Sleek Snake Chain And Stud Earrings Set
Style up your casual looks with this sleek necklace and dainty earrings set! It features a flat snake chain necklace with a V-shaped design and small round stud earrings. Pair this jewelry set with a statement ring to complete your trendy glam look.

Fit & Features
- Necklace and earrings set
- Flat snake chain necklace, V-shaped design
- Adjustable chain, lobster clasp closure
- Small round stud earrings
- Post-back closures
Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.
Style Number/Barcode: 07002-1329

Category Name: Vacation Looks

Price: $4.97 $11.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Barefoot Bliss Strapless Crochet Maxi
Sun, sand, and this dress—name a better trio. The strapless twist neckline and open-knit crochet bring breezy beach goddess vibes with zero effort required. Perfect for sunset cocktails on vacay or a beach date!

Fit & Features
- Crochet fabric, knit lining
- Strapless twist neckline
- Curve-hugging fit
- Center back slit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 06005-000011

Category Name: Vacation Looks

Price: $9.97 $46.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Stylish Silhouette Midi Sweater Dress
This curve-hugging sweater dress was made for sunset happy hour! It features a sleeveless V-neckline with a twist-front design, a center cutout under the bust, tank shoulder straps, and a midi-length, form-fitting silhouette with a chic high side slit. Style with classic hoop earrings and clear mules.

Shop More Sweater Dresses: Sweater Dress Collection

Fit & Features
- Sleeveless V-neckline, twist-front accent
- Center cutout under the bust
- Tank shoulder straps
- Midi-length hem, form-fitting silhouette, high side slit
- Ribbed sweater knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1462

Category Name: Vacation Looks

Price: $6.97 $46.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
LA Rider Graphic Seam Short Dress
Born to ride? Cruise through the streets of LA in this graphic short dress featuring cap sleeves, a crew neck, a front script that reads, " Motorcycle/Born to Ride/LA/CA Rider Crew", exposed seam detailing, and a front slit accent along the fitted hem. Complete the look in sleek sunglasses.

Fit & Features
- Cap sleeves
- Crew neck
- Exposed seam detailing
- Graphic script that reads, " Motorcycle/Born to Ride/LA/CA Rider Crew"
- Front slit accent, fitted hem
- Form-hugging fit, moderate stretch
- Fits true to size
Style Number/Barcode: 06002-1318

Category Name: Vacation Looks

Price: $6.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Totally Favored Denim Trucker Jacket
Your new favorite denim trucker jacket has arrived! It features long sleeves with elasticized cuffs, a collared neckline, four button-down front closures, flap pockets, and a cropped cinch drawstring hem. Complete the look in a basic top and sleek shorts.

Fit & Features
- Long sleeves, elasticized cuffs
- Collared neckline
- Four button-down front closures
- Flap pockets
- Cropped cinch drawstring hem
- Denim fabrication, no stretch
- Fits true to size
Style Number/Barcode: 06203-0466

Category Name: Vacation Looks

Price: $9.97 $46.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Heavenly Chic Mesh Cherub Corset
Look like absolute perfection in this mesh corset featuring a strapless neckline, flexible boning inserts, a cherub printed mesh overlay, and back hook-eye closures. Complete your chic look in a sleek mini skirt and heels.

Fit & Features
- Strapless neckline
- Flexible boning inserts
- Cherub printed mesh overlay
- Cropped hem
- Back hook-eye closures
- Fits true to size
Style Number/Barcode: 06001-4438

Category Name: Vacation Looks

Price: $6.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Sparkle Toes Rhinestone Mules
Sparkle down to your toes in these dressy stiletto mules designed with an on-trend, square toe, PVC strap with rhinestone mesh and a twist accent, and a faux leather footbed. Complete your formal look in a party dress.

Fit & Features
- Square toe
- Stiletto heel
- PVC strap, rhinestone mesh, twist accent
- Faux leather footbed
- Runs true to size
Style Number/Barcode: 07401-4078

Category Name: Vacation Looks

Price: $15.97 $30.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sweet Butterfly Charm Choker Set
Sweet and whimsy! Create a dreamy boho glam look with this two-pack choker set featuring one rhinestone choker and one butterfly charm choker each with a lobster clasp closure. Complete your dressy look with chic earrings.

Fit & Features
- Two-pack choker set
- One rhinestone choker
- One butterfly charm choker
- Each with a lobster clasp closure
Style Number/Barcode: 07002-1271

Category Name: Vacation Looks

Price: $4.97 $11.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Taylor High-Rise Skinny Ankle Jeans by Windsor Denim
This pair of Taylor skinny jeans by Windsor Denim will be a closet staple. They feature a high-rise waist, destructed detailing down the front, and a classic skinny leg fit. The denim fabric offers a moderate stretch for comfortable wear. Style with a crop top and mules.

Fit & Features
- High-rise waist
- Destructed detailing
- Skinny leg fit
- Five-pocket and belt loop design
- Front button, hidden zipper closure
- Denim fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06602-0359

Category Name: Vacation Looks

Price: $6.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
New Places High Rise Flare Denim Jeans
Wear these denim jeans to new places! They feature a flattering, high-rise waist and form-fitting hips, distressed knee accents, and a flared hem on vintage-inspired medium wash non-stretch denim fabric. Complete your trendy look in a bodysuit.

Fit & Features
- High-rise waist
- Form-fitting hips
- Distressed knee accents, flared hem
- Front button and hidden zipper closure
- Five-pocket styling, belt loop accents
- Medium wash non-stretch denim
- Fits true to size
Style Number/Barcode: 06602-0388

Category Name: Vacation Looks

Price: $6.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Chic Peek Dainty Layered Necklace
Give your outfit a chic peek of glam with this dainty layered necklace design with five lariat-styled layers, clear stone charms, and a lobster clasp closure. Complete the look in a low-cut long dress and clutch.

Fit & Features
- Five-lariat styled layers
- Clear stone charms
- Lobster clasp closure
- Dainty chain-links
Style Number/Barcode: 07002-1274

Category Name: Vacation Looks

Price: $5.97 $12.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Trendy Muse Layered Body Chain
You'll be a trendy muse when you accessorize with this dainty body chain! It features a layered design with a twisted chain and coin charms in a drop design. Style with your fave crop top and a chic mini skirt.

Fit & Features
- Layered body chain
- Twisted chain
- Coin charms, drop design
Style Number/Barcode: 07002-1265

Category Name: Vacation Looks

Price: $5.97 $14.90

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