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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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.

Sunshine On My Mind Strapless Tropical Skater Dress
This tropical skater dress will inspire sunshine on your mind! Perfect for vacations or a beach day, this strapless dress features a stretchy waist leading to the skater silhouette and a flirty ruffled mini-length hem. Complete the look in espadrille wedges.

Fit & Features
- Tropical palm print, gauze woven fabric, bust lining
- Strapless neckline
- Skater silhouette
- Ruffled hem
- Runs true to size
Style Number/Barcode: 05102-5744

Category Name: Vacation Looks

Price: $9.97 $35.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sweet Silhouette Rosette Ruffled Knit Mini Dress
The knit mini dress features a sleeveless scoop neckline accented with a dainty rosette detail for an adorable touch. The tiered ruffled mini-length hem and bodycon fit add a flirty feel while highlighting your curves.

Fit & Features
- Ribbed knit fabric with knit lining, plenty of stretch
- Scoop neckline with rosette detail
- Spaghetti straps
- Tiered ruffled mini-length hem
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5846

Category Name: Vacation Looks

Price: $9.97 $25.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Turn Heads Fringe Hoop Earrings
Giving major movement every time you turn your head. These fringe hoop earrings bring flirty vibes and just the right amount of drama to your outfit lineup.

Fit & Features
- Metal material
- Large thin hoop design
- Textured fringe disc detailing
- Omega closure
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-000042

Category Name: Vacation Looks

Price: $10.90

Availability: Out of Stock
Product Badge:
- Ships Free
Admiring Looks PVC Platform Mules
From casual outings to formal soirees, these platform mules are sure to receive admiring looks! Designed with clear PVC straps that offer a modern, barely-there look, these block heel mules add a chic edge to every look.

Fit & Features
- 3.5" Block heel
- Square toe
- Clear PVC straps
- Luxe fit cushioned insole
- Platform sole
- Faux leather material
- Runs true to size
Style Number/Barcode: 07401-000007

Category Name: Vacation Looks

Price: $32.90

Availability: Out of Stock
Product Badge:
- Ships Free
Blissful Afternoons Corset A-Line Midi Dress
Enjoy an afternoon of bliss looking so sweet in this A-line midi dress at showers or semi-formal weddings! The sweetheart neckline and adjustable spaghetti straps accentuate your figure while the corset bodice with built-in padded underwire bust provides support. The flowy A-line silhouette and midi-length hem add elegance to your look. Complete the look in strappy heeled sandals.

Fit & Features
- Woven fabric lined with stretchy knit
- Adjustable spaghetti straps
- Sweetheart neckline
- Corset bodice, built-in padded underwire bust
- Back zipper and hook-eye closure
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05101-3309

Category Name: Vacation Looks

Price: $9.97 $54.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Undeniable Halter V-Neck Crop Top
All you need is your undeniable sass and this crop top for an adorable style! It features a sultry halter V-neckline and a fitted pointed crop hem that flatters your figure on mineral wash stretchy rib knit fabric. Complete the look in jeans and sandals.

Fit & Features
- Mineral wash stretchy rib knit fabric
- Halter V-neckline
- Pointed crop hem
- Runs true to size
Style Number/Barcode: 06002-1880

Category Name: Vacation Looks

Price: $6.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Catch A Cutie Short Sleeve Cutout Eyelet Skater Dress
Catch yourself a cutie wearing this eyelet skater dress to day parties this season! With playful puff sleeves and a flirty cutout. The sweetheart neckline and bust drawstring add a touch of romance, while the skater silhouette and tiered ruffled hem keep it fun and flirty. Complete the look in wedge sandals.

Fit & Features
- Eyelet fabric lined with stretchy knit
- Sweetheart neckline
- Adjustable bust drawstring, cutout
- Skater silhouette
- Tiered ruffles
- Runs true to size
Style Number/Barcode: 05102-5430

Category Name: Vacation Looks

Price: $9.97 $49.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Leave An Impression Twist Cutout Knit Midi Dress
Leaving an impression will be easy with this sleeveless knit midi dress! Perfect for vacation or a weekend spent at the beach, this dress features a flattering scoop neckline, spaghetti straps, a head-turning twist cutout back design, a bodycon fit, and a sultry side slit along the midi-length hem. Complete the look in strappy espadrille wedges.

Fit & Features
- Knit fabric, moderate stretch
- Scoop neckline
- Spaghetti straps
- Twist back cutout
- Side slit
- Bodycon fit
- Runs true to size
Style Number/Barcode: 06005-1950

Category Name: Vacation Looks

Price: $17.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Artsy Scene Mock Neck Abstract Mini Dress
Indulge in the artsy scene in this mock neck abstract mini dress for downtown art walks! This sleeveless dress boasts a figure-flattering bodycon silhouette with side ruching, while the mini-length hem adds a flirty touch. The abstract print adds a bold and unique touch to this must-have dress. Complete the look in edgy boots and a shoulder bag.

Fit & Features
- Abstract print
- Mesh fabric, sewn-in knit lining, stretchy
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-5630

Category Name: Vacation Looks

Price: $19.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Out Of Office One Shoulder Tropical Maxi Dress
This tropical maxi dress says it's time for vacation! Switch your email to out of office and enjoy a sunny destination in this sleeveless dress featuring a one-shoulder neckline adorned with a knotted shoulder strap, a flattering mermaid silhouette, and a maxi-length hem. Complete the look with sunglasses and a cocktail in hand!

Fit & Features
- Tropical palm leaf print, stretchy knit fabric
- One-shoulder neckline
- Knotted shoulder strap
- Mermaid silhouette
- Runs true to size
Style Number/Barcode: 05102-5695

Category Name: Vacation Looks

Price: $9.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Legendary Style Western Buckle Faux Leather Sandals
It's impossible not to make an iconic fashion statement in these faux leather sandals! Featuring a sleek square toe, a flat sole, and a Western-inspired buckle along the strap for added flair. Complete the look with a trendy denim jacket.

Fit & Features
- Square toe
- Flat sole
- Western-inspired buckle on strap
- Faux leather material
- Runs true to size
Style Number/Barcode: 07404-1239

Category Name: Vacation Looks

Price: $9.97 $20.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Done In One Ribbed Knit Bodycon Midi Dress
Be ready in a flash with this done-in-one bodycon midi dress perfect for styling up or down! Made with stretchy ribbed knit fabric, it's also soft and comfortable to wear all day. It features a flattering scoop neckline and tank shoulder straps for a comfortable and stylish fit. With a bodycon silhouette and midi-length hem, this dress will hug your curves! Complete the look in a crop denim jacket and sandals.

Fit & Features
- Ribbed knit fabric, sewn-in knit lining, moderate stretch
- Scoop neckline
- Tank shoulder straps
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5666

Category Name: Vacation Looks

Price: $9.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Garden Glam Floral Maxi Dress
This isn’t your garden-variety maxi dress, floral abstract print meets daring cutouts and sleek hardware trim for a look that’s equal parts sultry and statement. Perfect for casual celebrations, destination nights, or when you’re ready to own the room.

Fit & Features
- Floral Abstract print, mesh-lined stretch fabric
- Strapless sweetheart neckline, hardware trim
- Cutout bodice
- Side ruched seams
- Curve-hugging, maxi-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000209

Category Name: Vacation Looks

Price: $42.90

Availability: In Stock

Available Color: BROWN

Available Size: XS, S, M, L
Girlycore Off-The-Shoulder Ruffled Skater Dress
Embrace a girly-core coquette aesthetic in this skater dress perfect for sunny days! The sweetheart neckline and cutout waist add a flirty touch, while the stretchy smocked bodice hugs your curves, and the ruffled tier short-length hem adds a feminine flair. Complete the look in wedge sandals.

Fit & Features
- Airy woven fabric with lining
- Stretchy smocked bodice with bust tie
- Cutout waist
- Ruffled tier skater silhouette
- Runs true to size
Style Number/Barcode: 05101-3054

Category Name: Vacation Looks

Price: $10.97 $48.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Cherry On Top Lace Trim V-Neck Mesh Mini Dress
This mesh mini dress is the cherry on top of your perfect summer! Featuring delicate lace trim V-neckline, adjustable spaghetti straps, and a cherry print on mesh fabric, this mini-length bodycon dress will hug your curves and flaunt your style. Complete the look in platform heels.

Fit & Features
- Cherry print, mesh fabric, stretchy knit lining
- Lace trim V-neckline
- Adjustable spaghetti straps
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5798

Category Name: Vacation Looks

Price: $9.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Pick Me Halter Floral Eyelet Crop Top
Pick this floral crop top for the sweetest look! This halter crop top features a flattering V-neckline with a spaghetti strap tie for a perfect fit, while a sweet bow detail adds a touch of charm. The fitted crop hem and floral printed eyelet fabric give off a playful, summertime vibe. Complete the look in high-rise jeans for any casual plans!

Fit & Features
- Floral printed eyelet fabric, minimal stretch
- Halter V-neckline, spaghetti strap tie
- Bow along the bust
- Fitted crop length
- Runs true to size
Style Number/Barcode: 06001-5365

Category Name: Vacation Looks

Price: $6.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Highly Favored Triangle Rhinestone Lariat Necklace
This lariat necklace will be highly favored over the rest! It features a dainty chain adorned with rhinestone charms leading to a sleek triangle charm with rhinestone trim and a single fringe chain with a rhinestone. Complete the look in a sultry cocktail dress for a rehearsal dinner or reception!

Fit & Features
- Dainy chain lariat necklace
- Rhinestone charms
- Triangle charm with rhinestone trim
- Single fringe chain with rhinestone
- Lobster clasp closure
Style Number/Barcode: 07002-1872

Category Name: Vacation Looks

Price: $2.97 $14.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Confident Flirty Strappy One-Shoulder Crop Top
Make your crush stop and stare at you in this sleeveless crop top! It boasts a flirty strappy one-shoulder neckline, and a fitted crop hem, and is made from a stretchy rib knit fabric. Complete the look in a denim mini skirt for any casual plans!

Fit & Features
- Stretchy rib knit fabric
- Strappy one-shoulder neckline
- Fitted crop hem
- Runs true to size
Style Number/Barcode: 06002-1878

Category Name: Vacation Looks

Price: $6.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Fall Into Fashion Crew Neck Open Back Maxi Dress
You'll be the cutest thing around in this sleeveless maxi dress all season! With its sleek crew neckline, alluring strappy open back, and flattering form-hugging fit, this dress is both stylish and versatile. Complete with a side slit and maxi-length hem, it's the perfect piece for any occasion. Style this maxi dress with earrings and sandals.

Fit & Features
- Stretchy rib knit fabric
- Crew neckline
- Strappy open back
- Side slit
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 05102-5654

Category Name: Vacation Looks

Price: $9.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Vacay Ready Tropical Knit Wide-Leg Pants
These alluring tropical wide-leg pants will have you ready for a dreamy vacay! The stretchy knit fabric features a bold abstract tropical print pattern to catch all the glances on your getaway. The pants are shaped with a high-rise elasticized waistband for comfortable wear and a relaxed wide-leg silhouette for a trendy look. Style with the matching crop top and hoop earrings.

Shop Matching Top: Vacay Ready Tropical Knit Halter Crop Top

Fit & Features
- Abstract tropical print
- Stretchy knit
- High elasticized waist
- Wide-leg silhouette
- Runs true to size
Style Number/Barcode: 06502-2481

Category Name: Vacation Looks

Price: $6.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Meet For Golden Hour Tie-Front Top
The top that turns sunsets into photo shoots. Designed with long flowy sleeves and a flirty tie-front, it's made for vacays, day dates, and spontaneous weekend plans.

Fit & Features
- Airy linen-blend woven fabric
- Long bell sleeves
- Tie-front closure
- Fitted ultra-cropped hem
- Runs true to size
Style Number/Barcode: 06204-000012

Category Name: Vacation Looks

Price: $14.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Boho Cutie Crochet Wide-Leg Pants
Show off the cutest boho vibe in these breezy crochet wide-leg pants! Designed with an airy sheer crochet knit fabric, these pants are perfect for summer days spent by the coast. They feature a high waist, a hip-hugging fit, and a wide-leg silhouette for that effortlessly chic vibe. Complete your look with the matching crop top and a pair of strappy sandals!

Shop Matching Top: Boho Cutie Bell Sleeve Crochet Crop Top

Fit & Features
- Sheer crochet knit fabric, moderate stretch
- High-rise elastic banded waist
- Hip-hugging fit
- Wide-leg silhouette
- Panty lining not included
- Runs true to size
Style Number/Barcode: 06502-2488

Category Name: Vacation Looks

Price: $9.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Much Love Sweetheart Swiss Dot Mesh Mini Dress
It's too easy to fall for this flirty swiss dot mesh mini dress perfect for soirees! The sweetheart neckline and padded bra cups provide a flattering fit, while the adjustable spaghetti straps and dual front ruched drawstrings allow for a customizable look. The bodycon fit and mini-length hem showcase your figure, all in a beautiful swiss dot mesh fabric. Complete the look in sandals.

Fit & Features
- Swiss dot mesh fabric, sewn-in knit lining, stretchy
- Adjustable spaghetti straps
- Back zipper and hook-eye closure
- Padded bra cups
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05101-3253

Category Name: Vacation Looks

Price: $9.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sweet Dreams Hanky Hem Floral Mini Dress
Sweet and dreamy will be your vibe in this adorable floral mini dress! Designed with a stretchy sheer mesh fabric with a knit lining for coverage, the short dress showcases a blooming floral print for the prettiest look. It features a sleeveless V-neckline with dainty lace trim for a feminine touch, spaghetti straps, a trendy drop waist silhouette, and a mini-length asymmetric hanky hem with a flowy A-line fit. Style with bow hair pins and strappy mules.

Fit & Features
- Floral print
- Stretchy sheer mesh fabric with knit lining
- V-neckline with lace trim
- Spaghetti straps
- Drop waist silhouette
- Asymmetric hanky hem, A-line fit
- Runs true to size
Style Number/Barcode: 05101-3462

Category Name: Vacation Looks

Price: $19.97 $36.90

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