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.
-
Coolest Look Aviator Metal Sunglasses
Make any outfit cool in these aviator sunglasses! They feature a sleek metal frame, smoke-tinted lense to help protect your eyes, and rubber nose supports and arms for comfort. Complete the look in trendy sandals.
Fit & Features
- Aviator sunglasses
- Sleek metal frames
- Smoke-tinted lense
- Rubber nose supports and arms
Style Number/Barcode: 07008-1101
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Sweet And Spicy Scoop Neck Mini Dress
Sweet and spicy, this mini dress is exactly what your next club night needs! It features a sleeveless scoop neckline, dual spaghetti straps, a strappy back design, and side ruched seams to accentuate your curves along the short bodycon silhouette. Complete the look in eye-catching stiletto heels.
Fit & Features
- Sleeveless scoop neckline
- Dual spaghetti straps
- Strappy back design
- Side ruched seams, bodycon silhouette
- Mini-length hem
- Slinky knit fabric, bust lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05103-4804
Category Name: Vacation Looks
Price: $19.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Perfectly Striped Shirt Skater Dress
Step out in this perfectly striped shirt dress to look cute for picnics in the park, family gatherings, or graduations! It features long sleeves with buttoned cuffs, a collar v-neckline, a corset-seam illusion waist, a cutout lace-up back design, and a short skater silhouette. Complete the look with teardrop earrings.
Fit & Features
- Long sleeves, buttoned cuffs
- Collar v-neckline
- Corset-seam illusion waist
- Cutout lace-up back design
- Skater silhouette, short-length hem
- Striped print, poplin non-stretch woven fabric
- Runs true to size
Style Number/Barcode: 05102-5048
Category Name: Vacation Looks
Price: $20.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Sweetest Sight Strapless Ruffled Eyelet Mini Dress
You'll be the sweetest sight in this strapless eyelet mini dress as the lovely bride-to-be or birthday girl! The strapless neckline and flexible boning provide a comfortable and flattering fit, while the tiered ruffled mini-length hem adds a playful touch. Complete the look with earrings and strappy block heels.
Fit & Features
- Eyelet woven fabric, sewn-in knit lining
- Strapless neckline
- Back zipper and hook-eye closure
- Flexible boning inserts
- Tiered ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05101-3042
Category Name: Vacation Looks
Price: $22.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Getaway Girl Halter Open Back Tropical Mini Dress
Getaway to paradise in this tropical mini dress! Featuring a sultry cowl halter neckline and an open back with dual spaghetti strap ties, this dress will show plenty of skin on vacay while the bodycon silhouette and mini-length hem flatter your figure. Complete the look with doorknocker earrings and heels.
Fit & Features
- Tropical print, mesh fabric lined with stretchy knit
- Halter cowl neckline
- Open back with dual spaghetti strap ties
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5795
Category Name: Vacation Looks
Price: $19.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Flutter Away Layered Skater Dress
Flutter away in a twirl-worthy skater dress! The dress features a sleeveless wrap V-neckline, adjustable spaghetti straps, and a tiered skater silhouette. The dress is composed of a lined chiffon fabric that offers a relaxed fit with a minimal stretch. Complete look with mules and dainty rings.
Fit & Features
- Sleeveless V-neckline, wrap-front design
- Adjustable spaghetti straps
- Back zipper, hook and eye closure
- Tiered skater skirt
- Chiffon fabric, knit lining, minimal stretch
- Fit and flare silhouette
- Runs true to size
Style Number/Barcode: 05101-1458
Category Name: Vacation Looks
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Just One Night Ruched Midi Dress
Make your night out a fab one with a dress that stuns! The dress features a sleeveless cowl neckline, spaghetti straps, curve-defining ruche detail, and a high-side slit for a display of leg along the midi-length hem. The dress is composed of a smooth knit fabric that offers a moderate stretch. Complete the look with mules.
Fit & Features
- Sleeveless cowl neckline, sticky bra recommended
- Spaghetti straps
- Ruching, high side slit
- Midi length hem
- Form-hugging fit
- Smooth knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05101-1107
Category Name: Vacation Looks
Price: $19.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Fierce Summer Vibes Rhinestone Fishnet Mini Dress
Layer on this fab rhinestone fishnet mini dress over short dresses, bodysuits, or swimsuits to give off fierce summer vibes! It features a crew neckline, short sleeves, a mini-length hem, a form-hugging fit, and all-over sparkling iridescent rhinestone embellishments on the sheer unlined fishnet fabric. Complete the look with sleek hoop earrings.
Fit & Features
- Crew neckline
- Short sleeves
- Mini-length hem
- Form-hugging fit
- Mini iridescent rhinestone embellishments
- Sheer unlined fishnet fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06001-4766
Category Name: Vacation Looks
Price: $19.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Basic Essential Ribbed Knit Midi Dress
This ribbed knit midi dress is a basic essential you need in your closet that you can dress up or down. It features a sleeveless square neckline, spaghetti straps, a mid-length, curve-hugging silhouette, and a stylish side slit. Keep this dress casual with sneakers, or elevate the look with chic mules.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Form-hugging fit
- Side slit, midi-length hem
- Double-lined rib knit fabric
- Moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4961
Category Name: Vacation Looks
Price: $19.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Cutest Babe Halter V-Neck Corset Crop Top
You'll be the cutest babe in this room in this sleeveless corset crop top! Featuring a flattering halter V-neckline, supportive underwire bust, and hidden front hook and eye fasteners, with figure-enhancing flexible boning while the cropped hem adds a touch of playfulness. Complete the look with the matching bottoms.
Shop Matching Bottoms: Cutest Babe Wide Leg Linen Trouser Pants
Fit & Features
- Woven fabric, sewn-in knit lining, no stretch
- Halter V-neckline
- Underwire bust
- Hidden front hook and eye fasteners
- Flexible boning
- Back zipper and hook-eye closure
- Cropped hem
- Runs true to size
Style Number/Barcode: 06003-2542
Category Name: Vacation Looks
Price: $15.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Cutest Vibe Ruched Knit Tube Top
Show off the cutest vibe in this trendy tube top with ruching down the sides for a flattering silhouette. Perf for styling with your fave pair of denim!
Fit & Features
- Cotton knit fabric, moderate stretch
- Strapless straight neckline
- Ruched side seams
- Mid-length hem
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06002-000512
Category Name: Vacation Looks
Price: $22.90
Availability: In Stock
Available Color: MOCHA-2, RED-2, BLUE
Available Size: XS, S, M
Product Badge:- Sale
-
It's The Tequila Talking Graphic Tee
Live your best life with this fun graphic tee that says it all! It features a crew neckline, short sleeves, a center script that reads "It's The Tequila Talking," and a cropped fit with a cute knot-front detail. Complete the look with distressed denim and hoop earrings.
Fit & Features
- Crew neckline
- Short sleeves
- Script that reads "It's The Tequila Talking"
- Cropped, form-hugging fit
- Knot-front detail
- Jersey knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 06002-1095
Category Name: Vacation Looks
Price: $6.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Modern Romance Sleeveless Lace-Up A-Line Midi Dress
Designed for a modern-day romance, this sleeveless woven midi dress is perfect for day dates! The sweetheart ruched neckline and adjustable straps are flattering, while the lace-up design cinches your waist for a beautiful silhouette. The front slit adds a touch of allure to this A-line midi-length dress. Complete the look in strappy wedges.
Fit & Features
- Texture woven fabrication with a woven lining
- Sweetheart neckline, ruched bust, dainty lace trim
- Adjustable straps
- Lace-up waist, stretchy smocked back
- Front slit
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-5722
Category Name: Vacation Looks
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Dressing For Sunshine Eyelet Lace Mini Dress
The perfect eyelet lace mini dress for sunny days! It features adorable puff short sleeves, a sweetheart neckline, a front bust ruched drawstring, and a bodycon silhouette. The eyelet lace fabric includes a knit lining and offers moderate stretch. Complete the look in this mini dress with cute sandals.
Fit & Features
- Puff short sleeves
- Sweetheart neckline
- Front bust ruched drawstring
- Bodycon silhouette
- Mini-length hem
- Eyelet lace fabric, knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5118
Category Name: Vacation Looks
Price: $19.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Twice The Love Rib Knit Midi Skirt
Dive into cozy rib knit love with this midi skirt! Perfect for everyday styling, this midi skirt features a high-rise elasticized waist and curve-flaunting bodycon silhouette and a side slit that shows some skin. Complete the look with the matching top.
Shop Matching Top: Twice The Love Rib Knit Crop Top
Fit & Features
- High-rise elasticized waist
- Bodycon silhouette
- Side slit
- Midi-length hem
- Rib knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06501-0937
Category Name: Vacation Looks
Price: $15.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Beachy Shell-Trim Straw Cowboy Hat
Capture the coastal cowgirl trend with this shell-trim cowboy hat perfect for breezy days by the water! Crafted with a woven straw material, it features a structured top, a wide brim with curved sides, and a seashell-beaded accent trim and long neck strap for those beachy vibes. Includes an interior elastic band. Style with a crochet top and jean shorts.
Fit & Features
- Woven straw material
- Structured top
- Wide brim, curved sides
- Shell-beaded accent trim and neck strap
- Interior elastic band
Style Number/Barcode: 07302-1612
Category Name: Vacation Looks
Price: $11.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Playful Icon Flat Jelly Slide Sandals
Playful jelly slides that elevate the iconic style you know and love for spring to summer! These fashion sandals feature a sleek square toe, a woven single band, and a comfortable flat sole on jelly material. Complete the look with a statement tote bag for a beach day or outdoor dinner party!
Fit & Features
- Square toe
- Woven single band
- Flat sole
- Slide on-and-off styling
- Jelly material
- Runs true to size
Style Number/Barcode: 07404-1196
Category Name: Vacation Looks
Price: $4.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
A Way With Lace V-Neck Mini Dress
Let this lace mini dress speak your favorite language, romance! The short dress features a sleeveless V-neckline, spaghetti straps, a bodycon silhouette, and a sheer lace overlay with a sewn-knit lining. Complete the look in rhinestone mules for a wedding shower or birthday brunch!
Fit & Features
- Sleeveless V-neckline
- Spaghetti straps
- Bodycon silhouette
- Mini-length hem
- Sheer lace overlay, sewn-in knit lining
- Minimal stretch
- Runs true to size
Style Number/Barcode: 05102-5088
Category Name: Vacation Looks
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Winged Goddess Butterfly Rhinestone Mules
Give your feet goddess vibes in these faux leather mules perfect for glam brides or cocktail soirees! They feature a square toe, a strappy design with butterflies and rhinestone embellishments, and a low-block heel. Complete the look with a sparkly clutch purse.
Fit & Features
- Square toe
- Strappy design
- Butterflies with rhinestone embellishments
- Low block heel
- Faux leather material
- Runs true to size
Style Number/Barcode: 07401-4204
Category Name: Vacation Looks
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Admiring Style Strapless Ruffle High Low Denim Dress
Prepare for plenty of admiring stares when you're in this stylish denim strapless dress! This cute and casual dress features a sweetheart neckline and form-hugging fit, accentuating your curves in all the right places. The patchwork seam detailing adds a touch of unique style, while the high-low ruffled hem adds a playful and flirty element. Complete the look in platform shoes and sunnies!
Fit & Features
- Denim fabric, slight stretch
- Strapless sweetheart neckline
- Back zipper and hook-eye closure
- Form-hugging fit
- Ruffle high low hem
- Runs true to size
Style Number/Barcode: 05102-5574
Category Name: Vacation Looks
Price: $9.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Sunny Fave Espadrille Platform Wedges
These adorable espadrille platform wedges will be a new fave for sunny weekend plans! With the trendy square toe and thin strappy design, you'll love styling them with your brunch dresses.
Fit & Features
- 4" Espadrille wedge heel
- Open square toe
- Asymmetric strappy design
- Adjustable ankle strap with buckle detail
- Platform design
- Luxe fit cushioned insole
- Runs true to size
Style Number/Barcode: 07406-0363
Category Name: Vacation Looks
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Dial B For Basics Square Neck Mini Dress
Dial B for this basic mini dress that'll inspire all your fashion-forward looks! It features a sleeveless square neckline, sleek bungee spaghetti straps, a form-hugging silhouette, and a mini-length hem. The double-line buttery knit fabric offers a seamless design and plenty of stretch. Style with a minimalistic necklace and earrings to inspire your day or night outfit!
Fit & Features
- Sleeveless square neckline
- Bungee spaghetti straps
- Form-hugging silhouette
- Mini-length hem
- Double-lined buttery knit fabric, moderate stretch
- Seamless design
- Runs true to size
Style Number/Barcode: 05102-5134
Category Name: Vacation Looks
Price: $9.97 $25.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Boho Style Crochet Hanky Hem Halter Top
Channel that trendy boho-chic style with this crochet knit halter top! The high halter neckline leads to a bold open-back design with cross-back tie straps offering an adjustable fit. The cropped asymmetric hanky hem will create a snatched look on the form-hugging silhouette. Pair with high-rise jeans and strappy sandals for a casual summer vibe.
Fit & Features
- Crochet knit fabric, moderate stretch
- Halter neckline
- Open back with cross-back tie straps
- Asymmetric hanky hem
- Fitted
- Runs true to size
Style Number/Barcode: 06005-1958
Category Name: Vacation Looks
Price: $6.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Pretty Cute Eyelet Lace Mini Dress
Achieve an effortless pretty and cute style in this eyelet lace mini dress for your casual dates or strolling downtown with the girls! The dress features adorable puff short sleeves, a ruffle trim sweetheart neckline with a front bust tie, a bodycon fit, and side ruching with an adjustable tie. Complete the look in trendy flat sandals.
Fit & Features
- Puff short sleeves
- Ruffle trim sweetheart neckline
- Front bust tie
- Bodycon silhouette
- Side ruching with adjustable tie
- Mini-length hem
- Eyelet lace fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05102-4912
Category Name: Vacation Looks
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale