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.
-
Oversized Straw Hat
The bigger the hat, the bigger the style! This must have straw hat features an oversized brim, a tassel accent and an all over straw material. Hat is adjustable for a custom fit. Offers UV protection.
Style Number/Barcode: 07302-1253
Category Name: Vacation Looks
Price: $7.48 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Braided Trim Panama Hat
This basic ivory panama hat is a must-have for this summer! It features a wide brim with a braided trim and an adjustable interior. Hat is composed of a woven straw material.
Style Number/Barcode: 07302-1258
Category Name: Vacation Looks
Price: $6.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Stylin' Straw Floppy Hat
Make your vacay a stylish one with this chic blush pink floppy hat! It features a wide floppy brim with a pink band. Hat is made of a straw material, is packable, and offers maximum UPF protection.
Style Number/Barcode: 07302-1239
Category Name: Vacation Looks
Price: $7.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Casual And Stylish Cargo Pocket Vest
When casual meets stylish like this sleeveless vest, you know it's going to be a closet staple! This vest features a collar neckline, a button-down front, and trendy cargo flap pockets for convenience, and a cropped hem for a modern touch. Complete the look in high-rise jean shorts for any occasion!
Fit & Features
- Windbreaker-type woven fabric, no stretch
- Collar neckline
- Button down front
- Cargo flap pockets
- Cropped length
- Runs true to size
Style Number/Barcode: 06204-1787
Category Name: Vacation Looks
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Banded Straw Panama Hat
This straw panama hat is so cute and perfect for the warmer months! It features a floppy brim with a chic black band and is made of a straw material.
Style Number/Barcode: 07302-1240
Category Name: Vacation Looks
Price: $6.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Cut Out Straw Floppy Hat
Amp up the festival scene with this trendy cut out floppy hat! It features a wide floppy brim with intricately designed cut outs. The black hat is composed of a straw material.
Style Number/Barcode: 07302-1243
Category Name: Vacation Looks
Price: $4.98 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Resort Ready Banded Boater Hat
Complete your resort ensemble with chic boater hat! This must have accessory features a faux straw weave and a mustard banded detail.
Style Number/Barcode: 07302-1232
Category Name: Vacation Looks
Price: $5.97 $15.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Sun Babe Floppy Straw Hat
Ready for those warmer days ahead?! We are! This cute floppy hat features a woven straw make with a laser cut design.
Style Number/Barcode: 07302-1234
Category Name: Vacation Looks
Price: $6.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Pretty In Pom Pom Straw Hat
Pep up your look with these cute pom poms! This natural straw hat features a wide-brim design and mini pink pom poms.
Style Number/Barcode: 07302-1237
Category Name: Vacation Looks
Price: $3.73 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Straw Sophistication Floppy Hat
Keep it sophisticated and stylish in this statement making straw hat! It features a natural hue, a tie accent and a floppy wide brim
Style Number/Barcode: 07302-1236
Category Name: Vacation Looks
Price: $7.97 $15.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Glimmer And Shimmer Hat
Glimmer and shimmer under that bright sun with this must have hat! It features a wide brim with an adorable black pom pom trim. Hat is composed of a gold glitter woven material.
Style Number/Barcode: 07302-1230
Category Name: Vacation Looks
Price: $3.73 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Braided Straw Sun Hat
Keep those bright sun rays off your face with this floppy straw hat. Featuring a flat top, a wide black band, and a broad brim to offer protection. This hat is made of a braided straw-like material, and is packable for those summer vacays!
Style Number/Barcode: 07302-1079
Category Name: Vacation Looks
Price: $12.90
Availability: Out of Stock
Product Badge:- Ships Free
-
Boater Hat
Bring some life into your hat game with this fashionable boater! Its sleek wool look with band accent will be perfect for completing your festival look!
Style Number/Barcode: 07302-1044
Category Name: Vacation Looks
Price: $12.90
Availability: Out of Stock
Product Badge:- Ships Free
-
Pom Pom Straw Hat
Take this adorable straw hat out to the park or the beach! This boater-style straw hat features a fun pom pom trim and a straw material that's perfect keeping the sun at bay.
Style Number/Barcode: 07302-1069
Category Name: Vacation Looks
Price: $14.90
Availability: Out of Stock
Product Badge:- Ships Free
-
Corduroy Cabbie Hat
Keep things trendy this fall with this style staple! The cabbie hat has a braided leather accent across the front and is composed of a corduroy material with a black woven lining.
Style Number/Barcode: 07302-0994
Category Name: Vacation Looks
Price: $12.90
Availability: Out of Stock
Product Badge:- Ships Free
-
Vibras Script Cap
It's good vibes only with this casual cap! It features an adjustable back strap, and a black "Vibras" script on the front.
Style Number/Barcode: 07302-0004
Category Name: Vacation Looks
Price: $4.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Draped In Gems Chain Skirt
Go for boho glam with this bold skirt! It features a high rise waist and a gold chain link design adorned with iridescent teardrop gemstones. Closes with a lobster clasp closure.Model is 5'6" with a 34" bust, 26" waist and 38" hips.
Style Number/Barcode: 07301-1059
Category Name: Vacation Looks
Price: $14.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Pair To Perfection Metallic Lace-Up Sneakers
These metallic sneakers pair perfectly with your everyday outfits. They feature a round-toe, a lace-up front closure, and a rubber gum sole.
Fit & Features
- Round toe
- Metallic material
- Lace-up front closure
- Rubber gum sole
- Runs true to size
Style Number/Barcode: 07407-0231
Category Name: Vacation Looks
Price: $10.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Tear Drop Dainty Chain Belt
Add a hint of shine to your look with a stylish chain belt! This must have features a double row design with a ball chain pattern and mini tear drop flat metal accents. Includes a lobster clasp closure for a custom fit.
Style Number/Barcode: 07301-1054
Category Name: Vacation Looks
Price: $4.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Always Wild O Ring Belt
Add this sleek belt to any outfit to amp it up! Belt features a gold, double O ring belt buckle, a black sleek design, and is composed of a faux leather.
Style Number/Barcode: 07301-0962
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Rhinestone Body Chain And Garter
This body chain and garter is definitely one way to look good in your birthday suit! Tease a little bling underneath your clothes. Body chain features a triple row of rhinestones that adorns your waist and is attached to rhinestone garters.
Style Number/Barcode: 07301-0899
Category Name: Vacation Looks
Price: $15.90
Availability: Out of Stock
Product Badge:- Ships Free
-
A Touch Of Love Wristlet
Add a touch of golden glam to your look with this trendy wristlet! The bag features a small gold beaded mesh design with an around the wrist handle, a magnetic button closure, and a top zipper closure. Interior is lined.
Style Number/Barcode: 07204-0418
Category Name: Vacation Looks
Price: $7.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Take A Bow Crossbody
All you need is a pretty bow to tie your look together! This natural crossbody features a top zippered closure, a saffiano body, a bow accent and a detachable chain shoulder strap. The interior features a black and white hued striped design with a small zippered pocket. The bottom features four gold hued peg accents. Crossbody is composed of a faux leather material.
Style Number/Barcode: 07203-1921
Category Name: Vacation Looks
Price: $13.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Box It Snake Print Clutch
House your essentials in this super trendy box clutch. It features a faux leather exterior with a red and black snake print, and a metal snap closure. Gold detachable chain included.
Style Number/Barcode: 07203-1916
Category Name: Vacation Looks
Price: $15.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance