Vacation Looks
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.
Now Trending
STYLE SPOTLIGHT
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.
-
Destination Bloom Flower Arm Cuff
The outfit was cute, but the flower arm cuff made it unforgettable. Designed with sculptural floral details and a wrapped silhouette, this statement piece brings an elevated finish to dresses, swim looks, and vacation outfits alike.
Fit & Features
- Metal wrap-around design
- Resin flower accents
Style Number/Barcode: 07003-000247
Category Name: Vacation Looks
Price: $14.90
Availability: Out of Stock
Product Badge:- Ships Free
-
Center Of Attention Floral Maxi Dress
This is the dress that gets the double-take. Designed with a curve-hugging mermaid silhouette and oversized floral print, it brings major romance with a little bit of drama.
Fit & Features
- Statement floral print, lined mesh fabric, high stretch
- Strapless tube neckline
- Curve-hugging, mermaid fit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000593
Category Name: Vacation Looks
Price: $19.97 $42.90
On Sale: Yes
Availability: In Stock
Available Color: BURGUNDY
Available Size: S, L
Product Badge:- Sale
-
Vacay-Coded Tropical Floral Print Maxi Skirt
Vacation-coded, curve-hugging, and not here to blend in. This tropical floral print maxi skirt brings a high-rise waist, a high-cut side slit, and ruched shaping that’s ready for rooftop reservations, vacation dinners, and every “where did you get that?” moment. Pair with the matching halter top.
Shop Matching Top: Vacay-Coded Tropical Floral Print Halter Top
Fit & Features
- Knit fabric with lining, high stretch
- Large tropical floral print
- High-rise waist
- High-cut side slit
- Maxi-length hem
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 06501-000169
Category Name: Vacation Looks
Price: $36.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
Product Badge:- Part of a Set
-
Resort Reserved Tropical Print Halter Jumpsuit
Vacation photos are about to have some competition. This tropical print halter jumpsuit pairs a draped cowl neckline with a striking beaded open back and flowy wide-leg silhouette that looks polished with almost zero effort.
Fit & Features
- Tropical printed woven fabric
- Sleeveless cowl neckline, halter strap
- Open back, beaded strappy design, lobster clasp closures
- Lower back zipper closure
- High waist seam
- Wide-leg silhouette
- Runs true to size
Style Number/Barcode: 06402-000036
Category Name: Vacation Looks
Price: $14.97 $69.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
- Tropical printed woven fabric
-
Coconut Coast Cutout Maxi Dress
Booked the trip and packed this tropical maxi dress that brings vacay vibes with a smocked fit, breezy skirt, and just the right amount of skin-baring detail. Pair with sandals and sunnies.
Fit & Features
- Tropical palm print, gauze-woven fabric
- Strapless sweetheart neckline
- Ruched drawstring tie-front bodice
- Cutout accent
- Flowy maxi silhouette
- Runs true to size
Style Number/Barcode: 05102-000601
Category Name: Vacation Looks
Price: $26.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Sleek Agenda Cowl Neck Halter Top
Fit & Features
- Sleek knit fabric, high stretch
- Sleeveless cowl neckline
- Tie-back halter spaghetti straps, beaded accents
- Open back
- Fitted mid-length hem, ruched detailing
- Runs true to size
Style Number/Barcode: 06001-000653
Category Name: Vacation Looks
Price: $32.90
Availability: In Stock
Available Color: WHITE, EGGPLANT
Available Size: XS, S, M, L
-
Vacay-Coded Tropical Floral Print Halter Top
Shop Matching Bottoms: Vacay-Coded Tropical Floral Print Maxi Skirt
Fit & Features
- Knit fabric with lining, high stretch
- Large tropical floral print
- Sleeveless plunging V-neckline, lace trim
- Halter strap, partially open back
- Ruched waist
- Mid-length hem, form-hugging fit
- Runs true to size
Style Number/Barcode: 06001-000665
Category Name: Vacation Looks
Price: $34.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
Product Badge:- Part of a Set
-
Packed For Paradise Hair Claw Clip
A little tropical touch goes a long way. This flower hair claw clip adds an instant vacation-ready vibe to messy buns, sleek twists, and beach-day waves.
Fit & Features
- Dual-sided tropical flower designs
- Sleek metal claw clip closure
Style Number/Barcode: 07006-000156
Category Name: Vacation Looks
Price: $6.97 $13.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Color Me Obsessed Tassel Hoop Earrings
A little sparkle was never going to be enough. These earrings feature colored baguette-cut rhinestones arranged in a dazzling circular hoop, oversized statement hoops, and tassel details that add a chic statement to your look.
Fit & Features
- Colored baguette-cut rhinestones
- Mini hoop design
- Statement tassel hoop with baguette-cut stones
- Post-back closure
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-000407
Category Name: Vacation Looks
Price: $8.97 $18.90
On Sale: Yes
Availability: In Stock
Available Color: PINK
Available Size: NS
Product Badge:- Sale
-
Weekend Upgrade Platform Wedges
The essential wedges of the season. With a lightweight platform wedge silhouette and cushioned thong straps, these sandals bring just the right amount of style for vacations, weekend brunches, and everything in between.
Fit & Features
- 3" Wedge heel
- Round toe
- Cushioned thong straps
- Platform sole
- Structured foam material
- Runs true to size
Style Number/Barcode: 07406-000055
Category Name: Vacation Looks
Price: $24.90
Availability: Out of Stock
Product Badge:- Ships Free
-
Flirty Style Paisley Print Asymmetrical Skort
This one's doing the flirting for you. This paisley print skort combines a curve-hugging fit with a ruffled silhouette for a look that feels effortlessly on-trend.
Shop Matching Top: Flirty Style Paisley Print Corset Tank Top
Fit & Features
- Lightweight woven fabric
- Mid-rise skort silhouette
- Paisley print
- Asymmetrical flowy overlay
- Hidden built-in-shorts
- Runs true to size
Style Number/Barcode: 06503-000338
Category Name: Vacation Looks
Price: $12.97 $29.90
On Sale: Yes
Availability: In Stock
Available Color: BLUE
Available Size: XS, S, M
Product Badge:- Sale
-
Booked For Sunset Halter Crop Top
The dress code just got a little more interesting. This crop top pairs a dramatic plunge neckline with floral applique details and an open back that was made for vacations, sunset cocktails, and parties.
Shop Matching Bottoms: Booked For Sunset Slit Maxi Skirt
Fit & Features
- Smooth knit stretchy fabric
- Plunge halter cowl neckline, tie straps
- Front flower inset
- Draped crop hem
- Open tie-back detail
- Runs true to size
Style Number/Barcode: 06001-000617
Category Name: Vacation Looks
Price: $12.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Booked For Sunset Slit Maxi Skirt
The dress code just got a little more interesting. This ruched maxi skirt pairs a dramatic thigh-high slit with floral applique details and a flowy silhouette that was made for vacations, sunset cocktails, and parties.
Shop Matching Top: Booked For Sunset Halter Crop Top
Fit & Features
- Smooth knit stretchy fabric
- Ruched mid-rise waist
- Flower inset
- Thigh-high slit
- Flowy maxi silhouette
- Runs true to size
Style Number/Barcode: 06501-000156
Category Name: Vacation Looks
Price: $34.90
Availability: Out of Stock
Product Badge:- Ships Free
-
One The Low Denim Shorts
The shorts that somehow make every outfit look better. These low-rise denim shorts bring an easy fit with cuffed hems and endless styling potential, whether you're heading to the boardwalk, a festival, or grabbing iced coffee.
Fit & Features
- Medium wash denim fabric
- Low-rise waist
- Form-hugging fit
- Cuffed hem
- Front button closure, belt loops, pockets
- Runs true to size
Style Number/Barcode: 06603-000196
Category Name: Vacation Looks
Price: $14.97 $36.90
On Sale: Yes
Availability: In Stock
Available Color: MED, DENIM
Available Size: S, M, L
Product Badge:- Sale
-
Breezy Vibe Tropical Print Tie-Front Top
Barely packed, fully planned. This tropical print tie-front top keeps it breezy with a plunging neckline, flowy sleeves, and an ultra-cropped fit that makes it feel instantly styled. Pair with the matching palazzo pants.
Shop Matching Bottoms: Breezy Vibe Tropical Print Palazzo Pants
Fit & Features
- Lightweight woven fabric, no stretch
- Tropical print
- Plunging V-neckline
- Tie-front design
- Short flowy sleeves
- Ultra-cropped hem
- Runs true to size
Style Number/Barcode: 06204-000149
Category Name: Vacation Looks
Price: $14.97 $32.90
On Sale: Yes
Availability: In Stock
Available Color: NATURAL
Available Size: S, M, L
Product Badge:- Sale
-
Breezy Vibe Tropical Print Palazzo Pants
Barely packed, fully planned. These tropical print palazzo pants keep it breezy with a lightweight woven fabric, pleated detailing, and a flowy, wide-leg fit that makes them feel instantly styled. Pair with the matching tie-front top.
Shop Matching Top: Breezy Vibe Tropical Print Tie-Front Top
Fit & Features
- Lightweight woven fabric
- Tropical print
- High-rise waist
- Pleated detailing
- Flowy wide-leg silhouette
- Runs true to size
Style Number/Barcode: 06302-000021
Category Name: Vacation Looks
Price: $18.97 $44.90
On Sale: Yes
Availability: In Stock
Available Color: NATURAL
Available Size: S
Product Badge:- Sale
-
Wild Card Printed A-Line Mini Dress
Vacation mood: activated. This printed A-line mini dress combines a flattering ruched fit with playful ruffles, making it an easy pick for rooftop drinks, weekend getaways, and every photo op in between.
Fit & Features
- Mesh fabric, knit lining, high stretch
- Tropical floral and animal multi-print pattern
- Sleeveless V-neckline
- Adjustable spaghetti straps
- Ruched bodice, V-shaped drop waist
- Tiered ruffled design with mini-length hem, A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-000796
Category Name: Vacation Looks
Price: $46.90
Availability: In Stock
Available Color: GREEN
Available Size: XS, S, M, L
-
Julyana Printed Ruffle Formal Dress
Special Occasion
Made for moonlit entrances and unforgettable evenings, this mesh gown brings dramatic movement to every step. The halter neckline, beaded tie detail, and tiered ruffle skirt create a striking silhouette that feels equal parts effortless and alluring.
Fit & Features
- Mixed animal print, mesh fabric, knit lining
- Halter neckline, spaghetti straps
- Open tie-back detail, zipper and hook-eye closure
- Layered ruffled A-line silhouette
- Floor-length hem
- Runs true to size
Where to Wear:
Destination weddings, vacations, honeymoons, cocktail parties, birthday dinners, engagement parties, fashion-forward events, formal celebrations
Style Number/Barcode: 05002-001435
Category Name: Vacation Looks
Price: $29.97 $99.90
On Sale: Yes
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L, XL
Product Badge:- Sale
-
Unforgettable Entrance Mesh Maxi Dress
This is the dress that changes the whole mood the second you walk in. With a plunging halter neckline, artful abstract print, and a curve-skimming silhouette finished with a dramatic front slit, it's made for weddings, formal events, and nights that deserve a memorable outfit.
Fit & Features
- Abstract print, mesh fabric, knit lining
- Halter neckline, tie straps
- High front slit
- Curve-hugging maxi silhouette
- Runs true to size
Style Number/Barcode: 05101-001514
Category Name: Vacation Looks
Price: $59.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L, XL
-
Coastal Getaway Printed Mini Dress
Your vacation itinerary just found its favorite outfit. This printed mini dress brings playful resort vibes with a chic A-line silhouette and postcard-inspired details, perfect for your next trip.
Fit & Features
- Linen-like fabric, woven lining
- Resort/paradise script and graphic pattern
- Square neckline, adjustable spaghetti straps
- Side zipper and hook-eye closure
- Side pockets, button-up front closures
- A-line mini silhouette
- Runs true to size
Style Number/Barcode: 05102-000817
Category Name: Vacation Looks
Price: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Blooming Agenda Floral Mesh Strapless Bustier
Booked, busy, and somehow still best dressed. This floral mesh bustier brings sculpted structure and a flattering fit that pairs perfectly with the matching skirt for any RSVP-worthy plan on your calendar.
Shop Matching Bottoms: Blooming Agenda Floral Mesh Maxi Skirt
Fit & Features
- Mesh fabric, high stretch
- Large floral print
- Strapless straight-across neckline
- Flexible boning
- Lace-up back design with tie closure
- Mid-length hem, form-hugging fit
- Runs true to size
Style Number/Barcode: 06001-000693
Category Name: Vacation Looks
Price: $15.97 $36.90
On Sale: Yes
Availability: In Stock
Available Color: ORANGE
Available Size: XS, S
Product Badge:- Sale
-
Blooming Agenda Floral Mesh Maxi Skirt
Booked, busy, and somehow still best dressed. This floral mesh maxi skirt brings a high-cut back slit and a curve-hugging fit that pairs perfectly with the matching bustier for any RSVP-worthy plan on your calendar.
Shop Matching Top: Blooming Agenda Floral Mesh Strapless Bustier
Fit & Features
- Mesh fabric with full-length knit lining, high stretch
- Large floral print
- High-rise waist
- High-cut back slit
- Maxi-length hem
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 06501-000183
Category Name: Vacation Looks
Price: $36.90
Availability: In Stock
Available Color: ORANGE
Available Size: XS, S, M, L
Product Badge:- Part of a Set
-
Polished Bloom Wrap Flower Arm Cuff
The arm cuff accessory that makes a simple outfit look styled in seconds. Featuring a wrap silhouette with sculpted floral accents, this arm cuff brings a romantic, fashion-forward feel to everything from vacation looks to special occasion dresses.
Fit & Features
- Metal wrap-around design
- Flower accents with rhinestone-embellished center insets
- Polished finish
Style Number/Barcode: 07003-000241
Category Name: Vacation Looks
Price: $12.90
Availability: In Stock
Available Color: SILVER
Available Size: NS
-
Pretty Shine Layered Stone Belly Chain
Tiny details, major outfit payoff. This layered stone belly chain adds the prettiest shine to low-rise denim, bikinis, matching sets, and every last minute “wait… this actually eats” look.
Fit & Features
- Two-row layered cross-over design
- Dainty chains
- Clear stone accents
- Lobster clasp closure with extender
- Adjustable fit
Style Number/Barcode: 07002-000446
Category Name: Vacation Looks
Price: $11.90
Availability: Out of Stock
Product Badge:- Ships Free