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.

In Search Of Luxe Gold Leaf Trim Hat
Your search for luxe ends here with this faux wool hat! It features a stunning gold leaf trim on a thin faux leather band and a wide brim. Complete the look in a polished plaid blazer.

Fit & Features
- Gold leaf trim, thin faux leather band
- Wide brim
- Faux wool material
Style Number/Barcode: 07302-1396

Category Name: Vacation Looks

Price: $5.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Charmed By You Sleeveless Lace Crop Top
Charm them all with your adorable flair in this sleeveless lace crop top! Made of soft knit floral lace fabric, it's both stylish and comfortable. It features a square neckline, bungee spaghetti straps, and a ruched bust for a flattering fit. Complete your look with light-wash jeans and sneakers.

Fit & Features
- Floral lace knit fabric, sewn-in lining, moderate stretch
- Bungee spaghetti straps
- Square neckline
- Cropped length
- Runs true to size
Style Number/Barcode: 06001-5184

Category Name: Vacation Looks

Price: $6.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Kiss the Spotlight Halter Romper
Flirty, flowy, and low-key iconic. This romper’s deep neckline and twirl-worthy shorts bring main feed energy to your night-out lineup.

Fit & Features
- Slinky knit stretchy fabric
- Halter plunge neckline, tie straps
- Open back
- Flowy shorts hem
- Runs true to size
Style Number/Barcode: 06503-000079

Category Name: Vacation Looks

Price: $44.90

Availability: In Stock

Available Color: BURGUNDY

Available Size: XS, S, M, L
Wear Your Art Striped Midi Dress
Wear this fine work of art and every eye will be on you! This marble striped midi dress features long sleeves, front and back v-necklines, a bodycon silhouette, and a tie-front waist. Complete the look in PVC mules for a casual lunch!

Fit & Features
- Long sleeves
- Front and back v-necklines
- Bodycon silhouette
- Tie-front waist
- Midi-length hem
- Marble striped print, stretch-knit fabric
- Fits true to size
Style Number/Barcode: 05102-4821

Category Name: Vacation Looks

Price: $9.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sweet One Off-The-Shoulder Crop Top
Show off your sweet side in this off-the-shoulder crop top perfect for summer fun! Features a sweetheart neckline and short sleeve cuffs for a flattering fit. The adjustable drawstring allows for a customizable look and the cropped hem adds a touch of trendiness. Complete the look in denim shorts and sandals for a day out!

Fit & Features
- Stretchy rib knit fabric
- Off-the-shoulder, sweetheart neckline
- Adjustable drawstring
- Cropped length
- Runs true to size
Style Number/Barcode: 06002-1865

Category Name: Vacation Looks

Price: $22.90

Availability: Out of Stock
Product Badge:
- Ships Free
Next Level Faux Suede Mini Skirt
Take your look to the next level with a mini skirt that slays! The skirt features a high-rise waist, a lattice tie-up front, and a mini-length hem. The skirt is composed of a lined faux suede fabric that offers a form-hugging fit with slight stretch. Complete look with a crop top and wedges.

Fit & Features
- High-rise waist
- Back zipper closure
- Lattice-tie front
- Mini-length hem
- Lined faux suede fabric
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06401-0457

Category Name: Vacation Looks

Price: $10.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Sweetly Femme Floral Corset Lace-Up Mini Dress
Sure to be a staple in your rotation, this super sweet floral mini dress is designed with a corset bodice and lace-up back that accentuates your femme figure along the A-line silhouette.

Fit & Features
- Floral print, chiffon-lined fabric
- Sweetheart neckline, bust tie, underwire bust
- Wide shoulder straps, side zipper and hook-eye clsoure
- Corset bodice, lace-up back
- A-line silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05101-4054

Category Name: Vacation Looks

Price: $9.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Effortlessly Pretty Chiffon Midi Dress
Showcase your effortless beauty in this airy, lightweight chiffon midi dress. It features a sweetheart neckline with a ruched bodice, long sheer peasant sleeves, a stretchy smocked back design, a fitted high waist seam, a midi-length hem with a high front slit, and a flowy, A-line silhouette. Style with clear mules for a weekend brunch date.

Fit & Features
- Sweetheart neckline, ruched bodice
- Long sheer peasant sleeves, elastic cinched hems
- Stretchy smocked back design
- Fitted high waist seam
- Midi-length hem, high front slit, A-line silhouette
- Sheer chiffon fabric, partial knit lining, minimal stretch
- Runs true to size
Style Number/Barcode: 05102-4954

Category Name: Vacation Looks

Price: $24.97 $54.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
90s Classic Patchwork Denim Bucket Hat
Experience the nostalgia of the 90s with this trendy patchwork denim bucket hat! It features a classic patchwork design on denim material and has adjustable inner strings to get the perfect fit. Complete the look in a denim mini dress!

Fit & Features
- Patchwork design, denim material
- Adjustable inner strings
- Bucket hat style
Style Number/Barcode: 07302-1614

Category Name: Vacation Looks

Price: $4.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Wanting More Strapless Lace Knit Maxi Dress
Leave everyone wanting more when you're in this lace knit maxi dress! Perfect for any summer plans, this dress flaunts a sleek strapless neckline and form-hugging fit that flares out into a long hem.

Fit & Features
- Lace knit fabric, lined
- Strapless neckline
- Form-hugging fit
- Flared maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000057

Category Name: Vacation Looks

Price: $9.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Seal The Deal Trouser Joggers
These casual and chic trouser joggers will have you business ready to take on the day! They feature a high-rise waist, pintuck pleated detailing, dual front pockets, a relaxed fit, and a trendy jogger hem. The lightweight woven fabric has no stretch. Style these pants with a bodysuit and a structured blazer.

Fit & Features
- High-rise waist, belt loops
- Hidden front zipper, hook and bar, and button closure
- Pintuck pleated detailing
- Dual front pockets
- Relaxed fit, elasticized jogger hem
- Woven fabric, no stretch
- Runs true to size
Style Number/Barcode: 06402-1280

Category Name: Vacation Looks

Price: $11.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Wanderlust Calling Strapless Abstract Flowy Tunic Top
Breeze into the sunny season in this strapless tunic top with a pretty abstract print on a flowy long silhouette and a flirty center slit design. Style as a cover-up or by itself on vacation, at festivals, or a beach day!

Fit & Features
- Abstract print, sheer chiffon fabric
- Strapless neckline with metal insert, bust lining
- Center slit design
- Flowy long silhouette
- Runs true to size
Style Number/Barcode: 06003-2751

Category Name: Vacation Looks

Price: $6.97 $54.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Seas The Day Pearl and Charm Statement Necklace
Giving total mermaid-on-vacay energy—and we’re obsessed. This pearl and charm necklace brings soft glam with a splash of beachy vibes, perfect for brunch plans or sunset selfies.

Fit & Features
- Faux pearl and charms
- Long chain
- Lobster clasp closure
Style Number/Barcode: 07002-000143

Category Name: Vacation Looks

Price: $9.90

Availability: In Stock

Available Color: GOLD

Available Size: NS
Alluring Marble Mesh Bodycon Dress
This alluring marble mesh bodycon dress will draw all the attention your way! It features a square neckline, sheer long fitted sleeves, a short, curve-hugging silhouette, and an all-over marble swirl pattern. The partially lined mesh fabric offers plenty of stretch. Style with platform heels.

Fit & Features
- Square neckline
- Sheer long fitted sleeves
- Mini-length hem
- Fitted bodycon silhouette
- Marble swirl pattern
- Sheer mesh fabric, partial knit lining, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4863

Category Name: Vacation Looks

Price: $9.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Faux Leather Paper Bag Tie Waist Shorts
Create a sleek and edgy look in these faux leather paper bag shorts. Step out in style in these high-waist shorts with side pockets and a matching self-tie belt. The faux leather material instantly makes dressy shorts the perfect bottoms to pair with your going-out looks for a girls' night out or clubbing. Pair these faux leather shorts with a mesh bodysuit or sparkly corset top for a fierce and sexy look.

Fit & Features
- High-rise paper bag waist
- Tie front belt
- Back zipper, hook and eye closure
- Side pockets
- Form-fitting style
- Faux leather fabric with moderate stretch
- Runs true to size
Style Number/Barcode: 06403-0146

Category Name: Vacation Looks

Price: $9.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Ray Of Sunshine Eyelet Lace Bustier
Look and feel like a ray of sunshine in this eyelet bustier for a flirty day date or weekend plans! The bustier is designed to snatch your figure while the ruffled crop hem adds the prettiest look to your favorite denim shorts.

Fit & Features
- Eyelet lace woven fabric
- Sweetheart neckline
- Adjustable shoulder straps
- Front hook and eye fasteners
- Stretchy smocked back
- Ruffled crop hem
- Runs true to size
Style Number/Barcode: 06003-2767

Category Name: Vacation Looks

Price: $6.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Kacey Formal Halter Pleated Long Dress
Special Occasion

Serve pure bliss in the Kacey formal dress designed for twirling all night at a wedding reception, banquet, or gala! She features an adorable halter neckline with a tie-back closure, an open-back, and a pleated flowy long-length silhouette. The formal dress is composed of a plisse airy fabric with no stretch. Complete your dressy look with a stunning hair accessory for a glam updo and lace-up heels.

Fit & Features
- Sleeveless halter neckline, tie-back closure
- Adhesive bra recommended
- Open-back design
- Hidden back zipper closure
- Pleated, flowy, long-length silhouette
- Plisse airy fabric, no stretch
- Runs true to size
Style Number/Barcode: 05002-3182

Category Name: Vacation Looks

Price: $9.97 $79.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Fawn Over You Marble Print Chiffon Skater Dress
You'll be fawned over when in this marble print chiffon skater dress! From the adjustable spaghetti straps to the flattering square neckline, this dress has got you covered. The stretchy smocked bodice creates a comfortable and perfect fit, while the tie waist belt accentuates your curves. With a playful ruffled tiered short-length hem, this dress is perfect for twirling! Complete the look in wedges for a dressy occasion.

Fit & Features
- Marble print, chiffon lined fabric
- Adjustable spaghetti straps
- Square neckline
- Tie waist belt, ruffled short-length hem
- Runs true to size
Style Number/Barcode: 05101-3081

Category Name: Vacation Looks

Price: $9.97 $54.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Feeling Pretty Cute Floral Skater Short Dress
Nothing comes as close to cute as this floral skater dress! Perfect for shower celebrations or afternoon teas, this short dress boasts a pretty corset-inspired bodice and a voluminous hem.

Fit & Features
- Floral print, cotton woven fabric, tulle and woven linings
- Square neckline, bust tie
- Wide shoulder straps
- Back zipper and hook-eye closure
- Corset-inspired bodice, pleating
- Skater silhouette, short-length hem, pleated trim
- Runs true to size
Style Number/Barcode: 05101-4037

Category Name: Vacation Looks

Price: $9.97 $49.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Trendy Style Belted Twill Skort
Show off a trendy style this summer season with this of-the-moment twill skort. It features a mid-rise waist with an adjustable faux leather belt, a hidden side zipper closure, a front skirt overlay with pleated detailing, shorts, and a fitted silhouette. Pair with a graphic tee and booties for a cool vibe.

Fit & Features
- Mid-rise waist, belt loops
- Adjustable faux leather belt, rectangular buckle
- Hidden side zipper closure
- Front skirt overlay, pleating, shorts
- Fitted silhouette
- Smooth twill fabric, no stretch
- Runs true to size
Style Number/Barcode: 06303-0238

Category Name: Vacation Looks

Price: $9.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Adoring Style V-Neck Tie Eyelet Skater Romper
Chanel this adoring and stylish eyelet skater romper for sweet summer looks at BBQs and Fourth of July parties! The V-neckline, spaghetti straps, and surplice bust provide a flattering fit, while the tie-back design adds a touch of sophistication. The skater silhouette and flowy short-length hem create an effortlessly chic look. Complete the look in wedge sandals.

Fit & Features
- Eyelet knit fabric, moderate stretch
- V-neckline
- Spagehtti straps
- Skater silhouette
- Runs true to size
Style Number/Barcode: 06503-1124

Category Name: Vacation Looks

Price: $16.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Summer Glam Espadrille Sequin Fringe Sandals
Slip into these espadrille sequin fringe sandals to glam up to your summer looks! Designed with a braided espadrille material, they feature a round toe, a wide strap across the foot with woven embroidery, shimmering sequins, and trendy fringe trims, and a flat sole. The open back offers effortless on-and-off styling. Pair with your flowy sundresses to create fabulous 'fits for your weekend plans!

Fit & Features
- Espadrille upper material
- Round toe
- Wide strap
- Woven embroidery, sequins, fringe trims
- Open back, flat sole
- On-and-off styling
- Runs true to size
Style Number/Barcode: 07404-1209

Category Name: Vacation Looks

Price: $9.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Kick Up The Style Cowboy Boots
Kick the dust off in these stylish faux leather cowboy boots perfect for music festivals and country bars! They feature a pointed toe, stacked block heel, classic western-inspired stitched designs, and a curved mid-length shaft with pull tabs to easily slide on and off. Complete the look in a fringe cowboy hat.

Fit & Features
- Pointed toe
- Stacked block heel
- Classic western-inspired stitched designs
- Mid-length shaft, pull tabs
- Faux leather material
- Runs true to size
Style Number/Barcode: 07403-1620

Category Name: Vacation Looks

Price: $12.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Take Me Away Crochet Tunic Sweater
Look good on the go in this crochet tunic sweater for your upcoming trip! Designed on sheer crochet fabric, it features long sleeves with chic flare cuffs, a crew neckline, and a sultry open-back design. Finished with a form-hugging fit and short-length hem. Style with sleek hoop earrings.

Fit & Features
- Long sleeves, flare cuffs
- Crew neckline
- Open back design
- Form-hugging
- Short-length
- Sheer crochet fabric
- Runs true to size
Style Number/Barcode: 06005-1828

Category Name: Vacation Looks

Price: $6.97 $34.90

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