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.

Chic Encore Crepe Slit Maxi Dress
Prepare for a standing ovation whenever you're seen in this crepe maxi dress perfect for casual wine nights by the fire pit or a spring getaway! Featuring a sleeveless square neck, spaghetti straps, a curve-hugging silhouette, and a sultry high slit along the flowy long hem. Complete the look in cute flat sandals.

Fit & Features
- Sleeveless square neck, spaghetti straps
- Curve-hugging silhouette
- Front high slit
- Flowy maxi-length hem
- Crepe knit fabric, mini-length knit lining
- Plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5058

Category Name: Vacation Looks

Price: $5.97 $38.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Beachside Babe O-Ring Triangle Bikini Top
Capture a babe look in this bikini top sitting beachside! The swimsuit top boasts classic triangle cups with a chic O-ring insert and dual adjustable back ties so you can customize the fit. Pair with the matching bikini bottoms.

Shop Matching Bikini Bottoms: Beachside Babe High-Rise Bikini Bottoms

Fit & Features
- Textured fabric
- Triangle cups, O-ring insert
- Removable padded bra cups
- Dual adjustable back ties
- Runs true to size
Style Number/Barcode: 07104-0715

Category Name: Vacation Looks

Price: $9.97 $25.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Sweet Fantasy Crepe Peplum Tube Top
You're always in for a sweet time in this crepe tube top designed with a flirty peplum silhouette and crop hem perfect for pairing with shorts.

Fit & Features
- Crepe woven fabric
- Strapless neckline
- Ruched bust, stretchy smocked waist
- Peplum crop hem
- Runs true to size
Style Number/Barcode: 06003-000033

Category Name: Vacation Looks

Price: $6.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Boost Your Glow Sequin Corset Top
Boost your glow in this shimmering sequin corset top featuring a sleeveless, square neck, tank-style straps, flexible boning, a fitted crop hem, and back hook-eye closures. Complete the look in a chic mini skirt and boots for a sparkly night out.

Fit & Features
- Sleeveless, square neck, tank-style straps
- Flexible boning
- Fitted crop hem
- Back hook-eye closures
- Sequin-knit, lined, minimal stretch
- Fits true to size
Style Number/Barcode: 06003-1948

Category Name: Vacation Looks

Price: $6.97 $38.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Cute Necessity Nylon Sling Fanny Pack
For all the concert cuties or sporty babes out there, this nylon sling fanny pack is a cute necessity to hold your essentials in style! This trendy fanny pack offers a detachable and adjustable long strap for multiple styling options, a back zipper pocket for extra storage, and a top zipper that reveals a spacious interior with four mesh pockets perfect for cards, keys, and cash. Complete the look in platform sneakers.

Fit & Features
- Detachable and adjustable long strap
- Back zipper pocket
- Top zipper
- Spacious interior with four mesh pockets
- Nylon woven material
Style Number/Barcode: 07203-1993

Category Name: Vacation Looks

Price: $5.97 $12.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Soiree Hour Lace-Up Ruffled Floral Midi Dress
When the cocktails are poured and the music starts playing it's time to unveil this floral chiffon midi dress! Perfect for daytime soirees or showers, this midi dress features a flattering scoop neckline adorned with adjustable spaghetti straps. The lace-up back and flowy ruffled silhouette offer a touch of trendiness to this midi-length dress! Complete the look with earrings and wedges.

Fit & Features
- Floral print, chiffon fabric lined with woven fabric
- Scoop neckline
- Adjustable spaghetti straps
- Lace-up back, zipper and hook-eye closure
- Flowy ruffled silhouette
- Runs true to size
Style Number/Barcode: 05101-3411

Category Name: Vacation Looks

Price: $9.97 $59.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sunset Beauty Off-The-Shoulder Marble Chiffon Crop Top
Radiate your beauty in this mesmerizing marble chiffon crop top on sunset beach walks! The breezy chiffon fabric is detailed with a pretty marble print for a dreamy vibe. The top features an off-the-shoulder neckline, long flowy bishop sleeves with cinched hems, a cropped cinched hem, and a relaxed fit for an effortless look. Style with denim shorts and sandals.

Fit & Features
- Marble-printed chiffon fabric, sewn-in knit lining
- Off-the-shoulder neckline
- Long bishop sleeves with cinched hems
- Cropped cinched hem
- Relaxed fit
- Runs true to size
Style Number/Barcode: 06003-2579

Category Name: Vacation Looks

Price: $6.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Mexico Tulum Graphic Tee
Grab your crew and head on vacay with this cute knit graphic tee with a paradise graphic and a script that reads "Mexico Tulum".

Fit & Features
- Stretchy cotton-blend knit fabric
- Short sleeves
- Crew neckline
- Paradise graphic, script reads "Mexico Tulum"
- Fitted crop hem
- Runs true to size
Style Number/Barcode: 06002-000037

Category Name: Vacation Looks

Price: $22.90

Availability: Out of Stock
Product Badge:
- Ships Free
Romance For Two High Rise Slit Maxi Skirt
You'll be sure to fall in love with this flowy maxi skirt for a dreamy summer wardrobe! With its elasticized high-rise waist, flowy tiered silhouette, and front slit, you'll feel effortlessly elegant. Complete the look with the matching top.

Shop Matching Top: Romance For Two Sleeveless Crop Top

Fit & Features
- Gauze woven fabric, short woven lining
- High-rise elasticized waist
- Front slit
- Flowy tiered silhouette
- Runs true to size
Style Number/Barcode: 06301-0189

Category Name: Vacation Looks

Price: $6.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Harper Mid-Rise Skinny Jeans By Windsor Denim
The jeans you never knew you needed! The Harper mid-rise jeans by Windsor denim will fit your body like a glove. She features a flattering skinny-leg design, and ankle-length hem, and is composed of clean dark wash denim with vintage-inspired color fading. Style with an edgy corset top for dinner and drinks!

Fit & Features
- Mid-rise waist
- Skinny-leg design
- Ankle-length hem
- Front button and hidden zipper closure
- Five-pocket styling, belt loop accents
- Clean dark wash denim, color fading, minimal stretch
- Runs true to size
Style Number/Barcode: 06602-0382

Category Name: Vacation Looks

Price: $16.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Shape Shift Resin Square Bangle Bracelet
Because your stack deserves a statement piece. This resin square bangle adds a bold, modern twist to your wrist game—wear it solo or layer for instant cool-girl points.

Fit & Features
- Smooth resin material
- Square bangle design
- Solid structured fit
- Lightweight and comfortable
Style Number/Barcode: 07003-000113

Category Name: Vacation Looks

Price: $11.90

Availability: In Stock

Available Color: BROWN

Available Size: NS
Classic Chic Mock Neck Sweater Dress
This classic chic sweater dress is perfect for styling up or down this winter season. It features an on-trend mock neckline, long fitted sleeves, a short, curve-hugging silhouette, and a front slit accent. The knit fabric offers plenty of stretch. Pair with knee-high boots and sleek hoops.

Fit & Features
- Ribbed mock neckline
- Long fitted sleeves
- Mini-length hem, front slit
- Curve-hugging silhouette
- Knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 06005-1616

Category Name: Vacation Looks

Price: $6.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Resort-Ready Tropical Print Mesh Duster
You'll be resort-ready when you pack this tropical print mesh duster in your carry-on! It features long fitted sleeves, an open front, a long-length hem with a flowy silhouette, and a multi-colored tropical print pattern on the airy sheer mesh fabric. Style over a mini dress with clear heels!

Fit & Features
- Long fitted sleeves
- Open front
- Long-length hem
- Flowy silhouette
- Multi-colored tropical print
- Sheer mesh fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 06202-0436

Category Name: Vacation Looks

Price: $9.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Simply Effortless Square Neck Rib Knit Bodysuit
All you need is this sleeveless basic bodysuit and your fave denim to create a simply effortless and cute look! Crafted from stretchy rib knit fabric that fits like a glove, this bodysuit boasts a square neckline, tank shoulder straps, and a thong bottom with snap-button closures for convenience. Style with high-rise denim jeans and sandals.

Fit & Features
- Stretchy rib knit fabric
- Square neckline
- Tank shoulder straps
- Thong bottom, snap-button closures
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 07109-0367

Category Name: Vacation Looks

Price: $9.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Back Of My Mind Crepe Slip Dress
You'll be unforgettable once they see you in this crepe slip dress perfect for casual parties and celebrations! It features a sleeveless V-neck, spaghetti straps, a form-hugging silhouette, and a sultry front slit along the midi-length hem. Style with simple hoop earrings to complete the look!

Fit & Features
- Sleeveless V-neck, spaghetti straps
- Form-hugging silhouette
- Front slit accent
- Midi-length hem
- Crepe fabric
- Moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4826

Category Name: Vacation Looks

Price: $9.97 $38.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Fave Trend Oversized Cat-Eye Sunglasses
These fab oversized cat-eye sunglasses will be your new fave trend to style up! They feature a cat-eye rimless design, a thin metal nose bridge, thin metal arms with a front cutout, rubber nose pads for support, and gradient-tinted lenses with stud accents. Pair with hoop earrings and a mini handbag for an everyday 'fit.

Fit & Features
- Oversized cat-eye rimless design
- Thin metal nose bridge and arms, cutout details
- Rubber nose pads
- Gradient-tinted lenses, stud details
- 100% UV protection
Style Number/Barcode: 07008-1073

Category Name: Vacation Looks

Price: $4.97 $9.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sweet Harmony Chiffon Midi Dress
Your sweet style personality goes in harmony with this chiffon midi dress perfect for any upcoming weddings and parties! The knee-length dress features short puff sleeves, a sweetheart neckline, princess seams, and a front flirty slit along the A-line silhouette. Pair with a chic ring set and heels.

Fit & Features
- Short puff sleeves
- Sweetheart neck
- Princess seams, front slit, back zipper and hook-eye closure
- A-line silhouette
- Midi-length hem
- Airy chiffon fabric, knit lining, no stretch
- Fits true to size
Style Number/Barcode: 05101-1850

Category Name: Vacation Looks

Price: $9.97 $46.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Romance For Two Sleeveless Crop Top
You'll be sure to fall in love with this crop top for a dreamy summer wardrobe! With its square neckline, adjustable spaghetti straps, and crop hem, you'll feel effortlessly elegant. Complete the look with the matching bottoms.

Shop Matching Bottoms: Romance For Two High Rise Slit Maxi Skirt

Fit & Features
- Gauze woven fabric, partially woven lining
- Adjustable spaghetti straps
- Square neckline
- Cropped length
- Runs true to size
Style Number/Barcode: 06003-2420

Category Name: Vacation Looks

Price: $6.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sight To See V-Neck Slip Dress
You'll be a sight to see in this casual slip dress perfect for dinner and drinks with your bae! It features a sleeveless v-neck, bungee spaghetti straps, a curve-hugging silhouette, and a short-length hem. Style with earrings and heels to complete the look!

Fit & Features
- Sleeveless v-neck
- Bust lining
- Bungee spaghetti straps
- Curve-hugging silhouette
- Short-length hem
- Texture knit design, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4840

Category Name: Vacation Looks

Price: $9.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Time To Vacay Halter Lace-Up Maxi Dress
Your next vacay fit is here - say aloha to this knit maxi dress designed to showcase your curves in a bodycon fit and bare some skin with the alluring lace-up back.

Fit & Features
- Texture knit fabric, knit lining, moderate stretch
- High halter neckline
- Spaghetti straps
- Lace-up back
- Bodycon fit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 06005-000053

Category Name: Vacation Looks

Price: $6.97 $46.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Hit The Basics Mock Neck Crop Top
A basic crop top like this is essential for creating the perfect capsule closet! It features fitted long sleeves, and a mock neck, and is composed of stretchy knit fabric. Style with jeans, a coat, and new shoes to complete the look!

Fit & Features
- Fitted long sleeves
- Mock neck
- Cropped hem
- Stretchy knit fabric, double-lined
- Runs true to size
Style Number/Barcode: 06002-1491

Category Name: Vacation Looks

Price: $6.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Fierce And Trendy Mid-Rise Leopard Mini Skort
Unleash your fierce and trendy side in this leopard mini skort! The belted waist and pleated skirt overlay create a trendy look while the mini hem shows off your legs.

Fit & Features
- Leopard print, denim fabric
- Mid-rise belted waist, belt loop accents
- Pleated skirt overlay, side zipper closure
- Shorts lining
- Mini-length hem
- Runs true to size
Style Number/Barcode: 06603-0430

Category Name: Vacation Looks

Price: $36.90

Availability: In Stock

Available Color: LEOPARD

Available Size: XS, S, M, L
Chill Cutie Cable Knit Sweater
Cutie alert! Keep chill and cozy in this cable knit sweater featuring long sleeves with ribbed cuffs, a surplice v-neckline, and a cropped hem of soft knit fabric. Complete the look in a basic cami and jeans.

Fit & Features
- Long sleeves with ribbed cuffs
- Surplice v-neckline
- Cropped hem
- Cable knit design
- Soft and comfortable
- Fits true to size
Style Number/Barcode: 06005-1484

Category Name: Vacation Looks

Price: $6.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Sun-Kissed Aesthetic Starfish High Slit Maxi Skirt
Achieve a sun-kissed aesthetic in this sultry maxi skirt boasting a high front slit with a beachy starfish accent. This skirt is perfect for vacations or pool parties!

Fit & Features
- Smooth stretchy knit fabric, panty lining
- Mid-rise waist
- Starfish accent
- High front slit
- Flowy maxi-length hem
- Runs true to size
Style Number/Barcode: 06501-000029

Category Name: Vacation Looks

Price: $13.97 $32.90

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