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.

Ready For My Vacay Bikini Top
You'll be totally ready for a summer vacay in this bright and bold bikini top. It features halter spaghetti straps, a sweetheart neckline with molded cups, a twist-front design, and a slide hook closure at the back. The all-over tropical print will look so stylish with a sheer flowy duster. Complete your poolside outfit with the matching bikini bottoms.

Shop Matching Bottoms: Ready For My Vacay Bikini Bottoms

Fit & Features
- Halter spaghetti straps
- Sweetheart neckline, molded cups
- Twist-front design
- Slide hook closure at the back
- Tropical print
- Runs true to size
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07104-0487

Category Name: Vacation Looks

Price: $9.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Walking Tall Over The Knee Boots
These over-the-knee boots were made for your daily stylish walks to and from the coffee shop! They feature a round toe, side zipper closure, PU front panel, a back knit panel, a flat sole, and low heel. Complete the look in a trendy crop jacket.

Fit & Features
- Round toe
- Side zipper closure
- PU front panel, back knit panel
- Flat sole
- Low heel
- Runs true to size
Style Number/Barcode: 07402-0839

Category Name: Vacation Looks

Price: $4.97 $40.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Denim Diva Platform Wedges
You'll be a total denim diva in these trendy wedges! They feature an open almond toe, a frayed detail toe strap, a frayed ankle strap with an adjustable buckle, and a platform wedge heel. Pair these wedges with a casual dress for a brunch ready look.

Fit & Features
- Open almond toe
- Frayed toe strap
- Frayed ankle strap, adjustable buckle
- Closed back
- Platform wedge heel
- Denim fabric
- Runs true to size
Style Number/Barcode: 07406-0249

Category Name: Vacation Looks

Price: $13.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
In The Details Faux Leather Platform Booties
You may want to get a close look to admire the details on these faux leather platform booties! They feature an almond toe, block heel, side knit panels, and zipper closure with an above-the-ankle shaft. Complete your edgy-girl look with a moto jacket!

Fit & Features
- Almond toe
- Block heel
- Platform sole
- Side knit panels and zipper closure
- Above-the-ankle shaft
- Faux leather material
- Runs true to size
Style Number/Barcode: 07403-1568

Category Name: Vacation Looks

Price: $10.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Tie The Knot Bow Strap Flat Sandals
Tie your outfit together in these cute flat sandals showcasing a square toe, a cutout strap with a knot bow, and a comfortable insole. Complete the look with a trendy handbag for any occasion!

Fit & Features
- Square toe
- Knot bow, cutout strap
- Flat sole
- Denim and beige are denim material
- Black is microsuede material
- Runs true to size
Style Number/Barcode: 07404-1222

Category Name: Vacation Looks

Price: $9.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Beachy Bombshell V-Cut Bikini Bottoms
Beachy bombshell will be your vibe in these V-cut waist bikini bottoms designed with lurex knit fabric for a trendy metallic sheen. Pair with the matching bikini top and sarong for a sun-kissed look!

Shop Matching Set: Beachy Bombshell Bikini Top, Beachy Bombshell One-Shoulder Bikini Top, Beachy Bombshell Short Sarong

Fit & Features
- Lurex knit fabric, metallic sheen
- V-cut waist
- Cheeky fit
- Runs true to size
- Returns are not accepted without the hygienic liner
Style Number/Barcode: 07105-0868

Category Name: Vacation Looks

Price: $6.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
First Sight Lug Block Heel Booties
It's love at first sight when you set your eyes on these faux leather booties featuring an almond toe, block heel, lug sole, side zipper closure, and an ankle-length fit. Complete the look in a cool moto jacket.

Fit & Features
- Almond toe
- Block heel
- Side zipper closure
- Lug sole
- Ankle-length fit
- Faux leather material
- Runs true to size
Style Number/Barcode: 07403-1609

Category Name: Vacation Looks

Price: $8.97 $38.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Coastal Crush Striped Crochet Tie-Front Crop Top
Made for sandy toes and sun-kissed selfies. This striped crochet crop top is your go-to for beach days, boat days, and flirty getaways—just add SPF and salty waves.

Fit & Features
- Crochet fabric, striped pattern
- Plunging V-neckline
- Tie-front design
- Long bell sleeves
- Ultra-cropped hem
- Runs true to size
Style Number/Barcode: 06204-000019

Category Name: Vacation Looks

Price: $15.97 $34.90

On Sale: Yes

Availability: In Stock

Available Color: MULTI

Available Size: S, M, L
Product Badge:
- Sale
Artistic Sensation Strapless Abstract Bubble Mini Dress
Anytime you step out in this artsy abstract strapless mini dress you'll attract all the attention! The strapless neckline highlights your curves, while the A-line silhouette flatters your figure. The fun and flirty bubble short-length hem adds a playful touch to any occasion. Complete the look with hoop earrings.

Fit & Features
- Abstract print, poplin woven fabric, sewn-in knit lining
- Strapless neckline, non-slip grip lining
- A-line silhouette
- Bubble short-length hem
- Runs small and short, recommend sizing up if needed
Style Number/Barcode: 05101-3450

Category Name: Vacation Looks

Price: $9.97 $49.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Make It Slay 50/50 Stiletto Boots
Make every outfit slay with these stiletto boots featuring a sleek pointed toe, side zipper closure, a knee-high shaft length, and a 50/50 faux leather and scuba knit material. Style with a longline coat for a dinner in the city!

Fit & Features
- Pointed toe
- Stiletto heel
- Side zipper closure
- Knee-high shaft length
- 50/50 faux leather, scuba knit material
- Runs true to size
Style Number/Barcode: 07402-0802

Category Name: Vacation Looks

Price: $4.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Effortlessly Elevated Strapless Linen-Blend Dress
Effortlessly elevated, this breezy linen-blend dress is such a summer staple. It features a strapless straight-across neckline, a secure back zipper closure, a ruched fitted high waist, hidden side pockets, and a flowy A-line mid-length silhouette for that relaxed casual-chic vibe. Style with espadrille sandals.

Fit & Features
- Linen-blend fabric
- Strapless straight neckline
- Back zipper hook-eye closure
- Ruched high waist
- Side pockets
- A-line fit, mid-length hem
- Runs true to size
Style Number/Barcode: 05102-5823

Category Name: Vacation Looks

Price: $20.97 $45.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Feeling Peachy Graphic Tube Top
Made for sunny day dressing, this graphic tube top showcases a front peach and graphic detailing that creates boldly cute looks!

Fit & Features
- Stretchy knit fabric
- Strapless neckline
- Peach and graphic detailing
- Fitted crop hem
- Runs true to size
Style Number/Barcode: 06002-000035

Category Name: Vacation Looks

Price: $22.90

Availability: Out of Stock
Product Badge:
- Ships Free
Made For Struts Over The Knee Boots
Made for stylish strutting down the street, you'll adore these faux leather over-the-knee boots featuring an almond toe, a stacked block heel, a side zipper closure, and a high shaft. Complete the look in a trendy sweater dress for a day in the city!

Fit & Features
- Almond toe
- Stacked block heel
- Side zipper closure
- High shaft, over the knee
- Faux leather material
- Runs true to size
Style Number/Barcode: 07402-0843

Category Name: Vacation Looks

Price: $4.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sleek Strut Knee-High Boots
This fall season, strut with style in these sleek knee-high boots! They feature a pointed toe, a sturdy block heel, an inner zipper closure, and a fitted shaft. Pair these faux leather boots with your favorite sweater dress.

Fit & Features
- Knee-high length
- Pointed toe
- Block heel
- Inner zipper closure
- Fitted shaft
- PU material, smooth lining
- Runs true to size
Style Number/Barcode: 07402-0793

Category Name: Vacation Looks

Price: $9.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Fleece Shaper Leggings
Comfy and flattering, these fleece leggings are perfect for lounging, traveling, and the office! They feature a high-waist fit with tummy control to smooth and shape your figure. These fleece-lined leggings will keep you cozy while appearing incredibly chic paired with an elevated crop top and tailored blazer or moto jacket for a fierce #OOTD look.

Fit & Features
- Tummy control waistband
- Skinny leg fit
- Cozy fleece-lined knit fabric
- Moderate stretch
- Sizes run small
Style Number/Barcode: 06502-1228

Category Name: Vacation Looks

Price: $6.97 $8.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Stylish Staple Henley Crop Top
This on-trend henley crop top is a stylish staple to add to your cart! It features a scoop neckline with a plunging notched front design, sleek metal grommet accents, long fitted sleeves, a fitted cropped hem, and a lower back cutout with a criss-cross strap design. Pair this ribbed knit top with cargo pants and mules.

Fit & Features
- Scoop neckline, plunging notched front design
- Metal grommet accents
- Long fitted sleeves
- Fitted cropped hem
- Lower back cutout, criss-cross strap design
- Ribbed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 06002-1495

Category Name: Vacation Looks

Price: $6.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Take Me Away High-Rise Palazzo Pants
These statement palazzo pants are ready to be whisked off on your next adventure! Made from linen-like cotton fabric, these pants offer a comfortable high-rise drawstring waist, convenient side pockets, and a flowy, wide-leg for stylish flair.

Fit & Features
- Linen-like cotton woven fabric
- High-rise elasticized drawstring waist
- Side pockets
- Flowy, wide-leg fit with seam details
- Runs true to size
Style Number/Barcode: 06302-000010

Category Name: Vacation Looks

Price: $6.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Festive Fun High-Rise Striped Palazzo Pants
Weekend activities just got a little cuter in these striped palazzo pants perfect for vacations or going to a summer fair! The high-rise elasticized waistband and pleating create a comfortable and flattering fit, while the wide-leg flowy silhouette and striped print bring a stylish touch. Complete the look with the matching top

Shop The Matching Top: Festive Fun Strapless Striped Bandeau Crop Top

Fit & Features
- Striped print, woven fabric
- High-rise elasticized waistband with pleating
- Wide-leg flowy silhouette
- Runs true to size
Style Number/Barcode: 06402-1424

Category Name: Vacation Looks

Price: $16.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Effortless Enchantment Floral Pleated Maxi Dress
This floral maxi dress brings the effortless, enchanted vibes to any occasion! With a sweetheart neckline and a pleated, flowy silhouette, you'll adore this dress all season long.

Fit & Features
- Floral print, chiffon fabric, stretchy knit lining
- Sweetheart neckline
- Adjustable spaghetti straps
- Tie-back detail, lower hidden zipper and hook-eye closure
- Pleated flowy silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-3914

Category Name: Vacation Looks

Price: $9.97 $59.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Serving Shade Square Oversized Sunglasses
These oversized square sunglasses with tinted lenses = instant it-girl upgrade!

Fit & Features
- Oversized square frames
- Tinted 100% UV protection lenses
- Smooth plastic frame with luxe finish
Style Number/Barcode: 07008-000007

Category Name: Vacation Looks

Price: $10.90

Availability: Out of Stock
Product Badge:
- Ships Free
Cozy Prep Collared Sweater
Cozy on up this fall while still keeping your look preppy with this cute collared sweater. It features a V-neckline with a trendy polo collar, long dolman-style sleeves, and a mid-length, relaxed fit. The soft ribbed knit fabric offers a moderate stretch for comfortable wear. Style this sweater with dark wash denim and booties.

Fit & Features
- V-neckline
- Polo collar
- Long dolman sleeves, tapered hems
- Mid-length, relaxed fit
- Ribbed knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1300

Category Name: Vacation Looks

Price: $16.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Destination Dinner V-Neck Midi Dress
Look fabulous in a flash wearing this sleeveless midi dress for dinner and drinks! It features a showstopping bodycon silhouette, a V-neck, tank straps, and side ruched seams that hug every curve like a glove. Complete the look with chic stiletto heels.

Fit & Features
- Sleeveless, V-neck, tank straps
- Side ruched seams
- Bodycon silhouette
- Midi-length hem
- Slinky knit fabric, knit lining, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4834

Category Name: Vacation Looks

Price: $9.97 $35.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sunny Oasis Halter Crop Top
Escape to a sunny destination with this alluring halter cowl crop top! Pair with the matching skirt to complete the trendy vibe.

Fit & Features
- Slinky knit stretchy fabric
- Halter cowl neckline, tie closure
- Side ruched seams
- Crop hem
- Runs true to size
Shop The Matching Skirt: Sunny Oasis Ruffle Mini Skirt
Style Number/Barcode: 06001-000145

Category Name: Vacation Looks

Price: $9.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Slinky Knit Wrap Front Top
The perf dressy top to take you from the office to happy hour. It features bishop long sleeves, a plunge V-neckline, and a wrap-style bodice, with tie-front detail along the cropped hem. Complete your look with high-rise pants and heels.

Fit & Features
- Bishop long sleeves
- Plunge V-neckline
- Wrap-style bodice
- Tie-front detail, crop hem
- Stretchy knit fabric
- Runs true to size
Style Number/Barcode: 06001-4708

Category Name: Vacation Looks

Price: $6.97 $26.90

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