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.

Sultry Snake Mesh Seam Detail Top
Look sultry in this snake mesh crop top featuring fitted, long sleeves, a crew neck, and on-trend seam detail on a cropped silhouette. Complete the look in a bralette.

Fit & Features
- Fitted long sleeves
- Crew neck
- Seam detail throughout
- Crop hem
- Snake pattern
- Sheer mesh fabric
- Fits true to size, moderate stretch
Style Number/Barcode: 06001-3888

Category Name: Vacation Looks

Price: $6.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
First Look Lace-Up Crop Top
This top is a must-have for making that stunning first impression! The top features an off-the-shoulder neckline, a sweetheart bust with a lace-up front, long sleeves, and a cropped hem. The top is composed of a lined smooth knit fabric that offers a form-hugging fit with a moderate stretch. Complete the look with the matching maxi skirt.

Shop Matching Maxi Skirt: First Look Ruched Maxi Skirt

Fit & Features
- Off-the-shoulder neckline
- Sweetheart bust
- Lace-up front
- Cropped hem
- Smooth knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06001-3925

Category Name: Vacation Looks

Price: $6.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
First Look Ruched Maxi Skirt
This skirt is a must-have for making that stunning first impression! The skirt features an elastic high rise waist, ruching throughout, a high side slit, and a maxi length hem. The skirt is composed of a lined smooth knit fabric that offers a form-hugging fit with a moderate stretch. Complete the look with the matching crop top.

Shop Matching Crop Top: First Look Lace-Up Crop Top

Fit & Features
- Elastic high-rise waist
- Ruching
- High side slit
- Maxi length hem
- Smooth knit fabric
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06501-0576

Category Name: Vacation Looks

Price: $6.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Stop and Stun Floral Slit Maxi Dress
Serving petal power with every step. This floral print maxi stuns with a draped cowl neckline and a high front slit that brings the drama (and the legs).

Fit & Features
- Floral print, mesh-lined fabric
- Cowl neckline
- Spaghetti straps
- Form-hugging fit
- High front slit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-000348

Category Name: Vacation Looks

Price: $9.97 $52.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Simple Staple Ribbed Knit Top
This ribbed knit top is a simple staple you need in your wardrobe! It features a scoop neckline, short sleeves, and a mid-length, form-hugging fit. Style this basic top with your fave pair of denim and a layered necklace.

Fit & Features
- Scoop neckline
- Short sleeves
- Mid-length, form-hugging fit
- Ribbed knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06002-1144

Category Name: Vacation Looks

Price: $6.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Breezy Floral Chiffon Short Kimono
Easy, breezy, and effortless, this floral chiffon kimono is the perfect layer! It features 3/4 length sleeves, an open-front design, and a high-low hem. Complete the look in a sultry slip dress and heels.

Fit & Features
- 3/4 length sleeves
- Open-front design
- Floral pattern
- High-low hem
- Airy chiffon fabric, no stretch
- Fits true to size
Style Number/Barcode: 06204-1152

Category Name: Vacation Looks

Price: $18.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Trendsetting Vibes Embroidered Denim Jacket
Bring the trendsetting vibes to your outfits this season with this cool light wash denim jacket. It features a collared neckline, long sleeves with buttons to cuff, a complete button-down front, pockets, an all-over embroidered star pattern, and a frayed hem. Style this jean jacket with aviator sunglasses and a cute crossbody purse.

Fit & Features
- Collared neckline
- Long sleeves, single buttons to cuff
- Button-down front
- Buttoned chest pockets, side pockets
- Embroidered star pattern, frayed hem
- Light wash denim fabric, no stretch
- Runs true to size
Style Number/Barcode: 06203-0460

Category Name: Vacation Looks

Price: $9.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Vintage Era Cat Eye Sunglasses
Create a head-to-toe vintage-inspired look starting with these cat-eye sunglasses! They feature a plastic frame, sturdy arms, and a curved lens. Complete the look in a trendy denim jacket.

Fit & Features
- Cat-eye style
- Plastic frames
- Sturdy arms
- Curved lens
Style Number/Barcode: 07008-0921

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Blossom With Beauty Floral Chiffon Kimono
Blossom with beauty in this breezy chiffon kimono! It features three-quarter length sleeves, an open front, a flowy silhouette, and an all-over floral print with pretty pastel hues. Style this kimono over a basic tank and denim shorts.

Fit & Features
- Three-quarter length sleeves
- Open front
- Flowy, relaxed fit
- Floral print
- Sheer chiffon fabric, no stretch
- Runs true to size
Style Number/Barcode: 06204-1155

Category Name: Vacation Looks

Price: $18.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sleek And Stunning Ruched Mini Skirt
Keep it sleek and stunning with a mini skirt that makes a stylish statement. The mini skirt features an elastic high-rise waist, ruched side seams, and a mini-length silhouette. The skirt is composed of a lined smooth knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with the matching crop top and mules.

Shop Matching Top: Sleek And Stunning Ruched Crop Top

Fit & Features
- Elastic high-rise waist
- Ruched side seams
- Mini-length silhouette
- Smooth knit fabric
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06501-0649

Category Name: Vacation Looks

Price: $9.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
See You Again Crepe Wrap Mini Dress
Flirty and cute, this crepe mini dress is perfect for running into your ex. It features a sleeveless square neckline, spaghetti straps, an open-back design with lace-up closure, and an asymmetrical wrap skirt with a side ruched seam. Complete the look in linear earrings and heels.

Fit & Features
- Sleeveless, square neck, spaghetti straps
- Open-back design with lace-up closure
- Asymmetrical wrap skirt
- Side ruched seam
- Bodycon silhouette, mini-length hem
- Crepe knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05103-4288

Category Name: Vacation Looks

Price: $9.97 $38.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Stylish Tribe High-Rise Flare Pants
Show up with your tribe looking so boho cute! This high-rise pant features an elasticized waist, a flared hem, and a tribal pattern on brushed knit fabric with a moderate stretch. Style with the matching bottoms.

Shop The Matching Top:

Fit & Features
- High-rise elasticized waist
- Flared hem
- Tribal pattern
- Pull-on/off styling
- Brushed knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 06502-0780

Category Name: Vacation Looks

Price: $9.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Handle It Draped Trench Coat
Handle your business in this high fashion trench coat. It features long sleeves, a draped collar neckline, and a belted tie waist. Composed of soft nylon-blend fabric with no stretch. Finish the look in sleek hoop earrings

Fit & Features
- Long sleeves
- Draped collar neckline
- Belted tie waist
- Soft nylon-blend fabric
- Fits true to size, no stretch
Style Number/Barcode: 06204-1354

Category Name: Vacation Looks

Price: $9.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sheer And Chic Tie Front Top
Keep it sheer and chic with a tie-front top to lay over your favorite bustier! The top features a plunging V-neckline, tie-front accent, long blousant sleeves, and a cropped hem. The top is composed of a sheer crinkle-textured woven fabric that offers a relaxed fit with minimal stretch.

Fit & Features
- Plunging V-neckline
- Tie-front accent
- Long blousant sleeves
- Cropped hem
- Crinkle-texture fabric
- Relaxed fit, minimal stretch
- Runs true to size
Style Number/Barcode: 06204-1051

Category Name: Vacation Looks

Price: $9.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Venom Snake Surplice Crop Top
Flaunt your sassy side in this snake print crop top featuring cap sleeves, a plunge v-neckline with a surplice accent, and side ruched detail that lets you adjust the fit. Complete the look in trendy jeans for a cute look.

Fit & Features
- Cap sleeves
- Plunge v-neckline
- Surplice accent, side ruched detail
- Snake print
- Cropped hem
- Brushed knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 06002-1118

Category Name: Vacation Looks

Price: $10.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Road Trip Distressed Denim Jacket
You can never go wrong in a classic denim jacket for your next road trip! It features long sleeves with button cuffs, a collared neckline, distressed accents, faux flap chest pockets, bottom slot pockets, and a button-down front. Complete the look in comfy joggers.

Fit & Features
- Long sleeves, button cuffs, collared neckline
- Faux flap chest pockets, bottom slot pockets
- Button-down front
- Distressed accents
- Denim fabric, no stretch
- Fits true to size
Style Number/Barcode: 06203-0197

Category Name: Vacation Looks

Price: $16.97 $37.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Tie The Knot Floral Crop Top
Take the plunge and rock this floral frock! It features long peasant sleeves, a plunge v-neckline with a tie-front, and an ultra cropped hem. This top is composed of chiffon woven fabric with no stretch. Complete the look in jeans.

Fit & Features
- Long peasant sleeves
- Plunge v-neck
- Tie-front
- Ultra cropped hem
- Floral pattern
- Woven chiffon fabric
- Fits true to size, no stretch
Style Number/Barcode: 06204-1223

Category Name: Vacation Looks

Price: $9.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Chic Factor Oversized Sunglasses
Amp up the chic factor of your everyday 'fits with these sleek oversized sunglasses. They feature an oversized slightly angled design with a thin gold metal frame and nose bridge, thin gold metal arms with long cutouts, tinted lenses, and built-in nose pads for support. Pair these stylish shades with hoop earrings.

Fit & Features
- Oversized angled design
- Thin gold metal frame and nose bridge
- Thin gold metal arms with long cutouts
- Tinted lenses
- Built-in nose pads
Style Number/Barcode: 07008-1097

Category Name: Vacation Looks

Price: $10.90

Availability: In Stock

Available Color: BLACK

Available Size: NS
Floral Forever Chiffon Mini Skirt
Floral will be forever trending! This cute mini skirt features a high-rise waist, back zipper closure, and a front ruched accent with tie closure on chiffon-lined fabric with no stretch. Finish the look in a sweater top for a girl's day.

Fit & Features
- High-rise waist
- Front ruched accent, tie closure
- Ditsy floral pattern
- Mini-length hem
- Back zipper closure
- Chiffon-lined fabric
- Fits true to size, no stretch
Style Number/Barcode: 06401-0430

Category Name: Vacation Looks

Price: $9.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Chic Number Keyhole Halter Dress
Keep it chic in this little number! Have a saucy night out in this halter mini dress featuring a twist halter neckline with a sultry keyhole and a bodycon silhouette. Complete the look in statement earrings.

Fit & Features
- Twist halter neckline
- Keyhole on front
- Bodycon silhouette
- Short length hem
- Slinky knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05103-4309

Category Name: Vacation Looks

Price: $9.97 $38.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Dazzle All Day Rhinestone Jelly Sandal
Dazzle all day in these rhinestone jelly sandals perfect for looking stylish on vacay! They feature a round toe, sparkly jelly sole, and T-strap design with adjustable buckle closure. Complete the look in a cute midi dress.

Fit & Features
- Rhinestone T-strap design
- Round toe
- Sparkly jelly sole
- Adjustable buckle closure
- Runs true to size
Style Number/Barcode: 07404-0984

Category Name: Vacation Looks

Price: $10.97 $14.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Feeling Fine Floral Midi Dress
Fel so fine in this floral midi dress for a chic brunch look! It features a sleeveless, v-neck, adjustable spaghetti straps, bodycon silhouette, asymmetrical hem, and a criss-cross back. Composed of stretchy knit fabric with an inner lining. Finish the look in heels.

Fit & Features
- Sleeveless, v-neck, adjustable spaghetti straps
- Criss-cross back straps
- Bodycon silhouette
- Asymmetrical midi hem
- Floral pattern
- Stretchy knit fabric, inner lining
- Fits true to size
Style Number/Barcode: 05101-1373

Category Name: Vacation Looks

Price: $9.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Style Goals Faux Leather Almond Toe Booties
Reach your style goals for the new year in these faux leather almond toe booties featuring a trendy block heel, side zipper closure, and an ankle-length fit. Complete the look in a sassy mini dress.

Fit & Features
- Almond toe
- Block heel
- Side zipper closure
- Ankle-length fit
- Faux leather material
- Runs true to size
Style Number/Barcode: 07403-1446

Category Name: Vacation Looks

Price: $12.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Butterfly Bae Chain-Link Anklet
Spread your glam wings! This chain-link anklet features three rhinestone butterfly charms, a layered design, and a lobster clasp closure. Complete the look in a sultry slit maxi dress.

Fit & Features
- Three rhinestone butterfly charms
- Layered design
- Chain-links
- Lobster clasp closure
Style Number/Barcode: 07003-0275

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free

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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