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.
HomeVacation Looks
Vacation Looks
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.
-
Chill And Unwind Ribbed Knit Pajama Romper
Unwind with a pajama romper that keeps it comfortable and stylish. The romper features a plunging V-neckline with a multi-button down front, short sleeves, and cheeky shorts. The romper is composed of a ribbed knit fabric that offers a form-hugging fit with a moderate stretch. Complete look slippers and a face mask.
Fit & Features
- V-neckline
- Multi-button down front
- Short sleeves
- Cheeky shorts
- Ribbed knit fabric
- Form hugging, moderate stretch
- Runs true to size
Style Number/Barcode: 07103-0514
Category Name: Vacation Looks
Price: $10.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
All Eyes On Me Cat Eye Sunglasses
Draw all eyes on you with stylish sunglasses that slay! The sunglasses feature a rounded cat-eye frame, dark lenses, and sleek hard plastic arms. Complete look with shorts and a crop top.
Fit & Features
- Rounded cat-eye frame
- Dark lenses
- Hard plastic arms
Style Number/Barcode: 07008-0860
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Shield Out The Shade Sunglasses
Shield out the haters with sunnies that command attention! The sunglasses feature an oversized shield frame, rimless lenses, studded accents, and wide hard plastic arms. Complete look with a crop top and biker shorts.
Fit & Features
- Oversized shield design
- Rimless lenses
- Studded accents
- Wide hard plastic arms
Style Number/Barcode: 07008-0849
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Dreamy Vacay Vibes Midi Dress
Get those dreamy vacay vibes in this stunning midi dress! It features a sleeveless V neckline, adjustable spaghetti straps, an asymmetric mid-length hem with a side slit, and a curve-hugging silhouette. The knit fabric has a gorgeous all-over tropical floral print. Complete the look with strappy sandals and some cute sunnies.
Fit & Features
- V neckline
- Adjustable spaghetti straps
- Asymmetric mid-length hem
- Side slit
- Form-hugging fit
- Knit fabric, floral print
- Runs true to size
Style Number/Barcode: 05102-0586
Category Name: Vacation Looks
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Current Fave Cutoff Denim Shorts
These high-rise cutoff denim shorts will be your new fave pair of the season! They feature a traditional five-pocket and belt loop design, distressed detailing, and an on-trend frayed cutoff hem. Style these shorts with a graphic tee and sneakers for a go-to casual look.
Fit & Features
- High-rise waist
- Traditional five-pocket and belt loop design
- Distressed detailing
- Frayed cutoff hem
- Denim fabric
- Runs true to size
Style Number/Barcode: 06603-0217
Category Name: Vacation Looks
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Fresh And Fab Cutoff Denim Shorts
Get a fresh and fab look this summer with these cute cutoff denim shorts! They feature a high-rise waist, a traditional five-pocket and belt loop design, a front button and hidden zipper closure, distressed detailing, and a cutoff hem. Style these shorts with a tie-front top and sandals.
Fit & Features
- High-rise waist
- Traditional five-pocket and belt loop design
- Front button and hidden zipper closure
- Distressed detailing, cutoff hem
- Denim fabric, no stretch
- Runs true to size
Style Number/Barcode: 06603-0193
Category Name: Vacation Looks
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Resort Calling Mesh Slit Maxi Skirt
Booked the trip? This skirt is already packed. Featuring a high-rise waist and dramatic slit skirt, this floral mesh moment is giving vacation muse energy—made for poolside lounges or rooftop cocktails.
Shop The Matching Top: Resort Calling Mesh Tie Front Top
Fit & Features
- Floral print, attached panty knit lining
- High-rise waist
- High front slit
- Flowy maxi length hem
- Runs true to size
Style Number/Barcode: 06501-000037
Category Name: Vacation Looks
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Sunny Days Ahead Cutoff Denim Shorts
Style up these cute cutoff denim shorts for an effortless summertime look! They feature a high-rise waist, a traditional five-pocket and belt loop design, a front button and hidden zipper closure, slight distressed detailing, and a frayed cutoff hem. Complete the outfit with a flowy blouse and sandals.
Fit & Features
- High-rise waist
- Traditional five-pocket and belt loop design
- Front button and hidden zipper closure
- Distressed detailing
- Frayed cutoff hem
- Denim fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06603-0190
Category Name: Vacation Looks
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Embraced In Glamour Straw Hat
Embrace a glam look with a hat that brings the flare! The hat features a fitted brim with a ribbon accent and a floppy design. The hat is composed of a straw-like material. Complete the look with a white dress and wedges for a derby-ready look!
Fit & Features
- Floppy design
- Fitted brim
- Ribbon accent
- Straw material
Style Number/Barcode: 07302-0309
Category Name: Vacation Looks
Price: $6.97 $13.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Swept Away Crochet Lace Maxi Dress
Get swept away in a crochet dress that keeps it casually cute! The dress features a sleeveless V-neckline, a crochet lace bodice, a double-row of spaghetti straps, an unlined crochet lace waistband, and a flowy maxi length silhouette. The dress is composed of a lined linen knit fabric that offers a relaxed fit with minimal stretch. Complete look with wedges.
Fit & Features
- Sleeveless V-neckline
- Crochet lace bodice
- Double-row of spaghetti straps
- Unlined crochet lace waistband
- Maxi length silhouette with lined skirt
- Linen knit fabric, relaxed fit, minimal stretch
- Runs true to size
Style Number/Barcode: 05101-0195
Category Name: Vacation Looks
Price: $18.97 $47.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Basic Faux Suede Halter Crop Top
Keep it basic and cute with a halter top that showcases a hint of skin! The crop top features a sleeveless halter neckline with halter neckties, a large keyhole at the center of the bodice, a mini lace-up detail, and a cropped hem. The top is composed of a lined faux suede fabric that offers a form-hugging fit with a moderate stretch. Complete look with a high waist mini skirt.
Fit & Features
- Halter neckline with halter neckties
- Keyhole
- Lace-up detail
- Cropped hem
- Faux suede fabric
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06001-3262
Category Name: Vacation Looks
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
A Clear Obsession Strappy Wedges
We have a clear obsession with these adorable strappy wedges! They feature an open almond toe, a clear PVC strap, an adjustable ankle strap with a buckle detail, and a cork wedge. Pair these shoes with a flirty skater dress and a classic denim jacket for a brunch date with the squad.
Fit & Features
- Open almond toe
- Clear PVC strap
- Adjustable ankle strap
- Buckle detail
- Cork wedge
Style Number/Barcode: 07406-0236
Category Name: Vacation Looks
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Get It Clear Cork Wedges
Get your love for wedges clearly across with these beauties! They feature an open almond toe, a clear PVC strap, an adjustable ankle strap with a buckle detail, and a cork wedge. Pair these shoes with a flirty skater dress and a classic denim jacket for a brunch date with the squad.
Fit & Features
- Open almond toe
- Clear PVC strap
- Adjustable ankle strap
- Buckle detail
- Cork wedge
Style Number/Barcode: 07406-0237
Category Name: Vacation Looks
Price: $7.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Fab And Frayed High-Rise Denim Shorts
Get a fab look this summer season with these trendy frayed denim shorts. They feature a high-rise waist, a traditional five-pocket and belt loop design, a front button and hidden zipper closure, and a destructed, frayed hem. Style these shorts with a graphic tee and combat boots for an edgy vibe.
Fit & Features
- High-rise waist
- Traditional five-pocket and belt loop design
- Front button and hidden zipper closure
- Destructed, frayed hem
- Denim fabric, no stretch
- Runs true to size
Style Number/Barcode: 06603-0195
Category Name: Vacation Looks
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Styled Up Gauze Crop Top
Style it up with a gauze top that elevates your outfits! The crop top features a plunging V-neckline, short flutter sleeves, and a cropped ruffled hem. The top is composed of a semi-sheer gauze fabric that offers a relaxed fit with minimal stretch. Complete look with high waist shorts.
Fit & Features
- V-neckline
- Short flutter sleeves
- Cropped ruffled hem
- Gauze fabric
- Relaxed fit, minimal stretch
- Runs true to size
Style Number/Barcode: 06003-1186
Category Name: Vacation Looks
Price: $4.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Sealed And Chic Faux Suede Bow Sandals
Seal your look with chic sandals that showcase your trendy taste! The sandals feature a slip-on design, an open almond toe, a wide strap over the toe with a pretty bow accent, and a flat footbed. The sandals are composed of a faux leather footbed and faux suede strap. Complete look with a romper and hoops.
Fit & Features
- Slip-on design
- Open almond toe
- Wide strap over the toe
- Bow accent
- Faux leather
- Faux suede
Style Number/Barcode: 07404-0710
Category Name: Vacation Looks
Price: $7.97 $20.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Pretty Fab Ditsy Floral Crop Top
Keep it pretty fab with a crop top that brings those sweet vibes. The crop top features a sleeveless square neckline, tie shoulder straps, a ditsy floral print, a cropped hem, and a smocked body. Complete the look with the matching skirt and mules.
Shop Matching Skirt: Pretty Fab Ditsy Floral Mini Skirt
Fit & Features
- Sleeveless square neckline
- Tie shoulder straps
- Ditsy floral print
- Cropped hem
- Smocked body
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06003-1256
Category Name: Vacation Looks
Price: $4.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
So Extra Floppy Straw Hat
Showcase how extra you are with a floppy hat that adorns your tresses! The hat features a fitted brim, an oversized floppy design, and is composed of a paper straw-like material. Complete look with a white dress and wedges for the perfect brunch outfit!
Fit & Features
- Fitted brim
- Oversized floppy design
- Straw-like material
Style Number/Barcode: 07302-0329
Category Name: Vacation Looks
Price: $6.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Magic Of Memories Abstract Halter Crop Top
Create fabulous memories in this crop top for any occasion! With a daring plunge halter neckline and gorgeous abstract print, you'll turn heads everywhere you go.
Fit & Features
- Abstract print, mesh-lined fabric
- Plunge halter neckline
- Fitted crop hem
- Runs true to size
Style Number/Barcode: 06001-000147
Category Name: Vacation Looks
Price: $6.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Boho Beauty Gauze Knit Kimono Duster
Channel those boho vibes with a duster that is perf to layer over your festival outfits or over your swimsuit! The duster features V-neckline, cute tie-front ties, an embroidered trim, short kimono sleeves, and a flowy long length. Complete look with a floppy hat and sunnies.
Fit & Features
- V-neckline
- Cute tie-front ties
- Embroidered trim
- Short kimono sleeves
- Flowy long length
- Gauze knit fabric
- Relaxed fit, minimal stretch, runs true to size
Style Number/Barcode: 06204-0820
Category Name: Vacation Looks
Price: $15.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Dreamy Boho-Chic Flare Pants
Showcase a dreamy vibe with these boho-chic flare pants! They feature a high-rise waist, flared-out pant legs, and a form-hugging fit. The knit fabric has a pretty all bohemian-inspired print for a trendy look. Complete the outfit with a crop top and strappy sandals.
Fit & Features
- High-rise waist
- Flared-out pant legs
- Form-hugging fit
- Knit fabric
- Bohemian-inspired print
- Runs true to size
Style Number/Barcode: 06502-0572
Category Name: Vacation Looks
Price: $13.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Flirty And Flowy Striped Woven Halter Top
She's flirty, she's flowy, she's your new fave halter top for the summer season. The lightweight striped woven fabric and open back keep it breezy, while the front flyaway design gives just the right amount of effortless edge.
Fit & Features
- Lightweight woven fabric, no stretch
- Striped pattern
- Sleeveless deep V-neckline, halter strap, elastic back
- Open back, tie-back spaghetti straps
- Flyaway front design
- Mid-length flowy fit
- Runs true to size
Style Number/Barcode: 06003-000087
Category Name: Vacation Looks
Price: $6.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Bold Babe Faux Leather Mules
Step out with mules that reveal your bold side! The mules feature an open back, an open square toe, a wide band over the toe, and a low block heel. The mules are composed of a faux leather material. Complete look with a ribbed tie-dye dress and hoops.
Fit & Features
- Open back
- Open square toe
- Wideband over the toe
- Low block heel
- Faux leather material
Style Number/Barcode: 07401-2772
Category Name: Vacation Looks
Price: $14.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Bohemian Beauty Satin Paisley Scarf
Showcase your boho side with a paisley scarf that adds a pretty detail to your outfit. The versatile scarf can be worn as a headwrap, crop top, hair tie, and more! The scarf features a bohemian-inspired print and is composed of a satin-like fabric. Complete look with hoops!
Fit & Features
- Bohemian print
- Satin-like material
Style Number/Barcode: 07305-0298
Category Name: Vacation Looks
Price: $4.97 $9.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free