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

Discover Short Sleeve Dresses

Capture On-Trend Sundresses

Get Eye-Catching Sandals For Women

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.

Stylish Basics Sleeveless Midi Dress
Keep it stylish with a midi dress that can be dressed up! The dress features a sleeveless V-neckline, spaghetti straps, and a midi-length silhouette. The dress is composed of a ribbed knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with clear mules and a metal cuff.

Fit & Features
- Sleeveless V-neckline
- Spaghetti straps
- Midi-length silhouette
- Ribbed knit fabric
- Form-hugging fit
- Moderate stretch
- Runs true to size
Style Number/Barcode: 06005-0947

Category Name: Vacation Looks

Price: $6.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
High Waist Tulip Pants
Keep it stylish and comfortable with these flared pants! The pants feature a high-rise waist and wide-leg tulip hems. Complete look with a crochet top and wedges.

Fit & Features
- High rise waist
- Tulip hem
- Flared
- Form hugging fit
- Runs true to size
Style Number/Barcode: 06302-0218

Category Name: Vacation Looks

Price: $9.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Basic Must-Have Midi Sweater Dress
This basic midi sweater dress is a must-have in your wardrobe. It features a sleeveless scoop neckline, tank shoulder straps, a mid-length, curve-hugging silhouette, and a ribbed sweater knit fabric that offers a moderate stretch. Style this dress with chic mules.

Fit & Features
- Sleeveless scoop neckline
- Tank shoulder straps
- Mid-length, form-hugging fit
- Ribbed sweater knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-0958

Category Name: Vacation Looks

Price: $13.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Red, White, And Booze Baseball Cap
Celebrate the Fourth of July with a cap that says it all! The cap features a script that reads: "Red, White & Booze" and a traditional baseball cap design. Complete look with an Americana-themed top and cutoff shorts.

Fit & Features
- Baseball cap design
- Short brim
- Script: "Red, White & Booze
- Adjustable back strap
Style Number/Barcode: 07302-0359

Category Name: Vacation Looks

Price: $6.97 $14.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
So Adored Cut Out Mini Dress
Feel so beloved in this pretty mini dress! The dress features a scoop neckline, short sleeves, a midriff cutoff with tie waist accent, and a mini-length silhouette. The dress is composed of a brushed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with platform heels.

Fit & Features
- Scoop neckline
- Short sleeves
- Midriff cutout, tie waist accent
- Mini length silhouette
- Brushed knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-1859

Category Name: Vacation Looks

Price: $19.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Level Up Cutout Mini Dress
Level up your look with a mini dress that brings all the details! The dress features a plunging V-neckline with a twist-front accent, adjustable spaghetti straps, sexy cutouts at the waist, and a mini-length silhouette. Complete look with platforms and hoop earrings.

Fit & Features
- Sleeveless V-neckline
- Twist-front accent
- Adjustable spaghetti straps
- Cutouts at the waist
- Mini length silhouette
- Form hugging fit
- Runs true to size
Style Number/Barcode: 06005-1003

Category Name: Vacation Looks

Price: $6.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Flirty And Fluttery Crop Top
Keep it fluttery and flirty with a crop top that is perf for your next date night! The top features a plunging V-neckline, short flutter sleeves, and a cropped hem with tie-back ties. Complete look with high waist jeans and mules.

Fit & Features
- Plunging V-neckline
- Short flutter sleeves
- Cropped hem
- Tie-back ties
- Linen fabric
- Relaxed fit, minimal stretch
- Runs true to size
Style Number/Barcode: 06003-1225

Category Name: Vacation Looks

Price: $4.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Effortlessly On-Trend Panama Hat
Top off your everyday look with this chic Panama hat to look effortlessly on-trend. It features a classic Panama hat design with a wide brim and a faux leather band. Complete your outfit with a layered charm necklace.

Fit & Features
- Classic Panama hat design
- Wide brim
- Faux leather band detail
- Faux wool material
Style Number/Barcode: 07302-0331

Category Name: Vacation Looks

Price: $8.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Glam Boho Leaf-Shaped Statement Earrings
Glam up your look and get a boho-chic style with these on-trend statement earrings. They feature a sleek round post attached to a beautifully detailed leaf-shaped design. Pair these earrings with a casual flowy dress for an effortless vibe.

Fit & Features
- Round metal post
- Metal detailed leaf-shaped design
Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.
Style Number/Barcode: 07001-0862

Category Name: Vacation Looks

Price: $4.97 $9.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Effortless Summer Striped Crop Top
The most effortless yet adorable crop top for summer! Flaunt your figure in this striped top with a trendy halter neckline and fitted silhouette perfect for styling with shorts.

Fit & Features
- Striped pattern, stretchy rib knit fabric
- Halter neckline, spaghetti strap ties
- Ruched bust
- Fitted crop hem
- Runs true to size
Style Number/Barcode: 06005-000003

Category Name: Vacation Looks

Price: $6.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Serving Sass Crepe Mini Dress
Serve up the sass in this bold mini dress! The short dress features a sleeveless scoop neckline, spaghetti straps, and a mini-length silhouette. The mini dress is composed of a crepe fabric that offers a form hugging fit with a moderate stretch. Complete look with clear heels and a rhinestone choker.

Fit & Features
- Sleeveless scoop neckline
- Spaghetti straps
- Mini length silhouette
- Crepe fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05103-2187

Category Name: Vacation Looks

Price: $19.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Major Headturner Cutout Midi Dress
Create a head-turning moment with a midi dress that slays! The dress features a sleeveless V-neckline, spaghetti straps, sexy waist cutouts, and a midi-length silhouette. Complete look with wedges and door knocker earrings.

Fit & Features
- Sleeveless V-neckline
- Spaghetti straps
- Waist cutouts
- Midi length silhouette
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-0961

Category Name: Vacation Looks

Price: $4.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sleek Style Ombre Sunglasses
These sleek shades will be your new go-to pair of the season! The sunglasses feature a square-shaped aviator style with a thin metal frame and tinted lenses with an ombre design. Complete the look with a chic shoulder bag.

Fit & Features
- Square-shaped aviator style
- Thin metal frame
- Tinted lenses with an ombre design
Style Number/Barcode: 07008-0876

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
All The Ruched Moves Cutout Mini Dress
Make all the right moves in a ruched dress that allures! The dress features a halter neck with a twist halter neck strap, a sexy cutout at the bust, a cutout at the midriff with sleek cross straps, and a mini-length silhouette with ruched drawstrings. Complete look with heels and a rhinestone anklet.

Fit & Features
- Halter neck
- Twist halter neck strap
- Cutout at the bust
- Cutout at the midriff, cross straps
- Mini length silhouette
- Dual ruched drawstrings
- Form hugging fit, runs true to size
Style Number/Barcode: 05103-3867

Category Name: Vacation Looks

Price: $19.97 $35.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Snake Chain And Cross Necklace Set
Layer on the style with a necklace set that elevates your look! One necklace features a trendy snake chain and the other necklace features a lariat design and cross charm. Complete look with a romper and wedges.

Fit & Features
- Two necklaces included
- Snake chain
- Lariat design
- Cross charm
Style Number/Barcode: 07002-0865

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Dainty Butterfly Charm Lariat Choker
Keep it dainty and sweet with a pretty lariat choker! The choker features a double-row dainty chain with small metal butterflies and a lariat charm. Complete look with a floral dress and wedges.

Fit & Features
- Double row
- Dainty chain
- Small flat metal butterflies
- Lariat charm
- Lobster clasp closure
Style Number/Barcode: 07002-0760

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Four-Pack Trendy Choker Necklace Set
Step up your style with this trendy choker necklace set! It features four necklaces with designs varying from a thick chain and dainty chain style to rhinestone detailing and a cute butterfly charm. Layer all four necklaces together and pair them with sleek hoop earrings.

Fit & Features
- Four choker necklaces
- Thick chain design
- Dainty chain style
- Rhinestones
- Butterfly charm
Style Number/Barcode: 07002-0737

Category Name: Vacation Looks

Price: $5.97 $12.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Major Must-Have Espadrille Platform Sandals
These on-trend espadrille sandals are a major must-have for this season! They feature an open round toe, a wide toe strap, an adjustable ankle strap, and an espadrille platform. Style these sandals with a floral dress and cute shades.

Fit & Features
- Open round toe
- Wide toe strap
- Adjustable ankle strap, buckle detail
- Heel strap
- Espadrille platform
- Runs true to size
Style Number/Barcode: 07404-0799

Category Name: Vacation Looks

Price: $12.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Stylish And Studded Espadrille Platform Wedges
Keep it stylish with studded platform wedges! The sandals feature an open back, a caged strap design, stud embellishments, an open almond toe, and an espadrille platform. Complete your look with a romper and hoop earrings.

Fit & Features
- Open back
- Caged strap design
- Open almond toe
- Stud embellishments
- Espadrille platform
Style Number/Barcode: 07406-0280

Category Name: Vacation Looks

Price: $7.97 $28.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Paisley Dreams Chiffon Crop Top
Keep it dreamy in a crop top that channels those wanderlust vibes! The top features an off-the-shoulder neckline, a paisley print, long bell sleeves, and a cropped hem. Complete the look with high waist jeans and mules.

Fit & Features
- Off the shoulder neckline
- Paisley print
- Long bell sleeves
- Cropped hem
- Chiffon fabric
- Relaxed fit, minimal stretch
- Runs true to size
Style Number/Barcode: 06003-1361

Category Name: Vacation Looks

Price: $6.97 $28.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Off The Shoulder Paisley Perfection Romper
Keep it chic with a bohemian-inspired romper that will have you brunch ready! The romper features a paisley print, an off-the-shoulder neckline, long bell sleeves, a tie waist belt, and wide-leg shorts. Complete the look with a butterfly necklace and wedges.

Fit & Features
- Off the shoulder neckline
- Long bell sleeves
- Tie-waist belt
- Wide leg shorts
- Paisley print
- Relaxed fit, minimal stretch
- Runs true to size
Style Number/Barcode: 06303-0130

Category Name: Vacation Looks

Price: $9.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Summertime Stunner Maxi Skirt
Showcase stunning looks on your summer vacay in this maxi skirt! It features a high-rise waist, dual thigh-high front slits, and a floor-length flowy silhouette. The lightweight gauze fabric has a trendy tropical leaf print, a perf look for a getaway! Style this skirt with the matching top.

Shop Matching Top: Summertime Stunner Crop Top

Fit & Features
- High-rise waist, elastic banded back
- Dual thigh-high front slits
- Floor-length flowy silhouette
- Gauze fabric, tropical leaf print, knit lining
- Runs true to size
Style Number/Barcode: 06301-0079

Category Name: Vacation Looks

Price: $13.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Summertime Stunner Crop Top
Showcase stunning looks on your summer vacay in this crop top! It features a sleeveless V-neckline with a tie-front detail, adjustable spaghetti straps, and a cropped, form-hugging fit. The lightweight gauze fabric has a trendy tropical leaf print, a perf look for a getaway! Style this top with the matching skirt.

Shop Matching Bottoms: Summertime Stunner Maxi Skirt

Fit & Features
- Sleeveless V-neckline
- Tie-front
- Adjustable spaghetti straps
- Stretchy smocked back
- Cropped, form-hugging fit
- Gauze fabric, tropical leaf print
- Runs true to size
Style Number/Barcode: 06003-1299

Category Name: Vacation Looks

Price: $6.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Gone Coastal Snake Side Tie Bikini Bottoms
If you're heading on vacay or the beach, these snake bikini bottoms will keep you fiercely stylish on and off the shore! Pair with the matching bikini top.

Fit & Features
- Snake print, lined fabric
- Low-rise waist
- Spaghetti strap side ties
- Cheeky coverage
- Runs true to size
- Returns are not accepted without the hygienic liner
Shop The Matching Bikini Bottoms: Gone Coastal Snake Triangle Bikini Top
Style Number/Barcode: 07105-0873

Category Name: Vacation Looks

Price: $6.97 $22.90

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