Summer Looks
Summer outfits that carry you from beach days to after-dark plans without missing a step. Matching sets keep things streamlined, while maxis, sundresses, and rompers deliver an easy, pulled-together feel, balanced by sharper staples like hot shorts, denim mini skirts, halters, and tube tops. Textures and prints stay in focus—crochet, mesh, florals, polka dots, and graphic tees—finished with sandals for a clean daytime look or styled up for wherever the night leads. From sunlit days to warm nights out, this edit moves effortlessly through vacation getaways, festivals, concerts, and GNO, blending relaxed, sun-ready pieces with elevated options for after dark.
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Summer Outfits That Shine from Dawn to Dusk
This season’s must-have summer outfits carry you from sunrise to sunset in effortless style. Head-turning sets in bold matching prints make you the center of attention at day parties and night scenes. Brunch-ready dresses—flirty minis, midis, and maxis in breezy linen, airy cotton, and floaty chiffon—are made for café hangs and sunset selfies. Polished day-to-night vibes come through crisp linen rompers and tailored crop-and-skirt combos, keeping you sharp at the office and effortlessly chic for after-hours. Effortless essentials like graphic tees with lace shorts or lightweight crop tops paired with denim deliver stress-free style on those “too busy to think” days.
Star-spangled pieces in red, white, and blue lend a festive touch to your 4th of July looks and Labor Day outfits. For laid‑back holiday weekends, playful rompers and skorts channel joyful backyard party vibes, while tropical-print matching sets and mesh-panel tanks slide seamlessly into vacation and resort wardrobes.
Curated for vacations, getaways, and holiday trips, don't miss the latest updates to 2026 summer dress trends! Statement accessories—faux leather wedges or strappy sandals—provide the perfect finishing flourish, and Windsor’s latest summer formal dress collection offers elevated options for sunlit soirées.
Finish every look with strappy sandals or espadrille wedges and find fresh seasonal colors like coral, sage, and sky blue. Finding what to wear is even easier with Windsor's fashion blog with the latest tea on the best summer party looks!
These summer outfits flow from bright mornings to balmy evenings, making every moment inherently style‑worthy. Ready to build your ultimate warm‑weather wardrobe? Explore Windsor’s full edit of summer outfits—online, in‑app, or at your nearest Windsor store. Your new go‑to look awaits!
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Pop The Cork Sling Back Wedges
Your next wine tasting calls for these cork wedges featuring a sling-back ankle with adjustable buckle closure, almond toe, and a faux leather footbed. Complete the look in a flowy maxi dress.
Fit & Features
- Almond toe
- Sling back ankle, adjustable buckle closure
- Faux leather footbed
- Cork wedge heel
- Runs true to size
Style Number/Barcode: 07406-0293
Category Name: Summer Looks
Price: $15.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Happy Flower V-Neck Crochet Romper
You'll be one happy flower in this adorable V-neck romper featuring a sleeveless bodice, adjustable spaghetti straps, and a sheer crochet waist atop flowy shorts on floral printed chiffon fabric. Complete the look in sandals for the perf spring outfit.
Fit & Features
- Sleeveless, V-neck, adjustable spaghetti straps
- Sheer crochet waist
- Back zipper, hook and eye closure
- Flowy shorts
- Floral chiffon fabric, knit lining, minimal stretch
- Runs true to size
Style Number/Barcode: 06403-0209
Category Name: Summer Looks
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Breezy Boho-Chic Tie-Front Top
Breezy and so boho-chic, this airy chiffon top is a summer staple. It features long bishop sleeves, a V-neckline, a tie-front design, and a cropped fit. The sheer chiffon fabric features an all-over dainty floral print and a polka dot textured pattern. Style over a basic mini dress with mules.
Fit & Features
- Long bishop sleeves, elasticized hems
- V-neckline
- Tie-front
- Cropped
- Floral print, polka dot textured pattern
- Sheer chiffon fabric, no stretch
- Runs true to size
Style Number/Barcode: 06204-1150
Category Name: Summer Looks
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Earn Your Stripes Sweater Midi Dress
Earn your stripes in style rocking this sweater midi dress for all-day slays! It features a sleeveless square neck, adjustable spaghetti straps, a striped pattern, and a bodycon silhouette. Composed of a rib-knit fabric with a moderate stretch. Style with chic booties.
Shop More Sweater Dresses: Sweater Dress Collection
Fit & Features
- Sleeveless square neckline
- Adjustable spaghetti straps
- Striped pattern
- Bodycon midi-length hem
- Rib-knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1240
Category Name: Summer Looks
Price: $17.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Level Up High-Rise Denim Shorts
Elevate your casual style with shorts that are perf for a day out! The shorts feature a high-rise waist, a single button with zipper closure, a traditional five-pocket with belt loop design, heavy destruction, and cutoff hem. Complete look with a crop top and slides.
Fit & Features
- High-rise waist
- Cutoff hem, heavy destruction
- Five-pocket and belt loop design
- Front button and hidden zipper closure
- Medium wash denim fabric
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06603-0296
Category Name: Summer Looks
Price: $9.97 $37.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Bring The Heat Printed Midi Skirt
Bring the heat to your vacay look with this sultry midi skirt! It features a high-rise waist, chic ruched detailing down the sides, a midi-length, curve-hugging fit, and an all-over tropical palm leaf print. Style with the matching tube top and strappy mules.
Shop Matching Top: Bring The Heat Printed Tube Top
Fit & Features
- High-rise elasticized waist
- Ruching down the sides
- Midi-length, form-fitting silhouette
- Tropical palm leaf print
- Sheer mesh fabric, full knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 06501-0541
Category Name: Summer Looks
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Cutest Look Floral Mini Dress
Get the cutest look for the spring season with this adorable floral mini dress! It features a sleeveless sweetheart neckline with shirring at the bust, spaghetti straps, a short, curve-hugging fit, and an all-over dainty floral print pattern. Style this dress with a cropped denim jacket and strappy sandals.
Fit & Features
- Sleeveless sweetheart neckline
- Shirring at the bust
- Spaghetti straps
- Mini-length, form-fitting silhouette
- Floral print
- Brushed knit fabric, knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4612
Category Name: Summer Looks
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Tropical Dream Tube Top
Let this tube top transport you to an island paradise! The top features a sleeveless square tube design, a pretty tropical print, and a cropped hem. The top is composed of a smooth knit fabric that offers a form-hugging fit with a moderate stretch. Complete the look with the matching maxi skirt.
Shop Matching Maxi Skirt: Tropical Dream Maxi Skirt
Fit & Features
- Sleeveless square neckline
- Tropical palm leaf print
- Cropped hem
- Lined smooth knit fabric
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06001-3746
Category Name: Summer Looks
Price: $6.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Tropical Dream Maxi Skirt
Let this maxi skirt transport you to an island paradise! The skirt features a pretty tropical print, a high-side slit, and a maxi-length silhouette. The skirt is composed of a lined smooth knit fabric that offers a form-hugging fit with a moderate stretch. Complete the look with the matching tube top.
Shop Matching Tube Top: Tropical Dream Tube Top
Fit & Features
- Elastic high-rise waist
- Tropical palm leaf print
- High side slit
- Maxi length silhouette
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06501-0537
Category Name: Summer Looks
Price: $12.97 $31.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Floral Muse Chiffon Kimono
You'll be a total muse in this breezy and chic chiffon kimono! It features three-quarter length sleeves, a flowy high-low silhouette, and an all-over blooming floral print. Layer this lightweight kimono over a neutral mini dress.
Fit & Features
- Three-quarter length sleeves
- Flowy high-low silhouette
- Floral print
- Sheer chiffon fabric, no stretch
- Runs true to size
Style Number/Barcode: 06204-1036
Category Name: Summer Looks
Price: $18.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Chill Out Smocked Joggers
Chill out in joggers that are perf to dress down in but still look cute! The joggers feature a high-rise smocked waist, a drawstring, hidden side pockets, and a straight leg with a smocked tapered leg. Complete look with a ribbed bodysuit and sandals.
Fit & Features
- High-rise smocked waist
- Drawstring
- Hidden side pockets, back pockets
- Straight leg, smocked tapered leg
- Woven fabric
- Relaxed fit, minimal stretch
- Runs true to size
Style Number/Barcode: 06302-0643
Category Name: Summer Looks
Price: $29.90
Availability: Out of Stock
Product Badge:- Clearance
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Callie Sleeveless Satin Midi Dress
Special Occasion
The Callie satin midi dress will keep your formal looks sleek and oh-so-chic! She features a sleeveless cowl neckline, adjustable spaghetti straps for a customized fit, front ruching at the waist, and a mid-length, wrap-front fitted silhouette creating a front slit. Style this dress with pretty hoops and clear heels.
Fit & Features
- Sleeveless cowl neckline, adjustable spaghetti straps
- Strapless or adhesive bra recommended
- Ruching at the waist
- Mid-length, wrap front skirt
- Back zipper, hook and eye closure
- Satin fabric, woven lining
- Fitted silhouette, no stretch
- Runs true to size
Style Number/Barcode: 05001-0759
Category Name: Summer Looks
Price: $29.97 $56.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Ditsy Blooms Lace-Up Crop Top
Ditsy and cute, this crop top is in full bloom for spring! It features short puff sleeves, a square neck, and an open back with a lace-up closure. Composed of a brushed knit with a moderate stretch. Style with the matching bottoms.
Shop Matching Bottoms: Ditsy Blooms Ruched Mini Skirt
Fit & Features
- Short puff sleeves, elasticized hems
- Square neck
- Cropped hem
- Open-back, lace-up closure
- Ditsy floral pattern
- Brushed knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06001-3839
Category Name: Summer Looks
Price: $6.97 $21.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Ditsy Blooms Ruched Mini Skirt
Ditsy and cute, this mini skirt is in full bloom for spring! It features a high-rise waist, a side ruched seam that accentuates your curves on the form-fitting silhouette. Composed of a brushed knit with a moderate stretch. Style with the matching top.
Shop Matching Top: Ditsy Blooms Lace-Up Crop Top
Fit & Features
- High-rise waist
- Side ruched seam
- Form-fitting silhouette
- Mini-length hem
- Ditsy floral pattern
- Brushed knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06501-0556
Category Name: Summer Looks
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Easy Breezy Eyelet Skater Dress
Easy, breezy, and flirty! This eyelet skater dress is perfect for your next spring fling. It features a sleeveless, square neck, spaghetti straps, high waist seam, and a trendy open-back with twist detail on the flared short silhouette. The dress is composed of a lined lightweight woven knit fabric that offers a flattering form hugging fit with a moderate stretch. Complete the look in espadrille sandals.
Fit & Features
- Sleeveless, square neck, spaghetti straps
- High waist seam
- Open-back with twist detail
- Flared short silhouette
- Eyelet pattern
- Lined lightweight woven knit fabric
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05102-4415
Category Name: Summer Looks
Price: $6.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Summer Awaits Halter Crop Top
Get a summer-approved look with this trendy halter crop top. It features a handkerchief top design with a sleeveless halter neckline with tie-back straps, a completely open back with lower tie-back straps, and a cropped fit with an angled hem. Style this top with distressed denim or cute flare pants.
Fit & Features
- Handkerchief top design
- Sleeveless halter neckline, tie-back straps
- Open back, lower tie-back straps
- Cropped fit, angled hem
- Sweater knit fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06005-1290
Category Name: Summer Looks
Price: $6.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Daydream With Me Satin Floral Skirt
Look like a total daydream in this satin floral mini skirt featuring a high-rise waist, a fitted silhouette, a flirty front slit accent, and a back zipper closure. Complete the look in a boho-style top for brunch.
Fit & Features
- High-rise waist
- Fitted silhouette
- Front slit accent
- Back zipper closure
- Mini-length hem
- Floral satin fabric, no stretch
- Runs true to size
Style Number/Barcode: 06401-0446
Category Name: Summer Looks
Price: $6.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Go With It Cropped Denim Jacket
Go with the flow in a cropped denim jacket that is perf to layer over your casual outfits! The jacket features a collared neckline, a multi-button down front, two chest pockets with a single button closure, long sleeves, and an elastic cropped hem. The jacket is composed of denim fabric that offers a relaxed oversized fit with a minimal stretch. Complete look with a midi dress and mules.
Fit & Features
- Collared neckline
- Multi-button down front
- Two chest pockets
- Long sleeves
- Elastic cropped hem
- Denim fabric
- Relaxed fit, minimal stretch, runs true to size
Style Number/Barcode: 06203-0200
Category Name: Summer Looks
Price: $39.90
Availability: Out of Stock
Product Badge:- Sale
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High Waist Linen Shorts
Fall back on basic shorts with a stylish twist! These shorts are ready for warmer days with a high-rise waist, a tie-waist belt, a wide leg hem, and a back zipper closure for a secure fit. Complete look with a floral bodysuit and wedges for the perfect brunch outfit with the squad!
Fit & Features
- High-rise waist
- Tie-waist belt
- Wide leg hem
- Back zipper closure
- Lined linen fabric
- Relaxed fit, minimal stretch
- Runs true to size
Style Number/Barcode: 06303-0150
Category Name: Summer Looks
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Girl's Trip Boho Slit Maxi Skirt
Grab the girls, book the flight, and pack this cute boho maxi skirt! It features a high-rise waist, a front slit, and a long hem. Complete the look in the matching top.
Shop Matching Top: Girl's Trip Boho Tie-Front Top
Fit & Features
- High-rise waist
- Front slit
- Long hem
- Boho pattern
- Runs true to size
Style Number/Barcode: 06301-0104
Category Name: Summer Looks
Price: $13.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Seashore Stroll Drawstring Linen Joggers
These drawstring linen joggers are perfect for your daily strolls by the seashore! They feature a high-rise elasticized waist with a front tie closure, a four-pocket design, a slim-fit leg, and elasticized cuffs. Complete the look in a basic bodysuit and sandals.
Fit & Features
- High-rise elasticized waist
- Drawstring front tie-closure
- Four-pocket design
- Slim-fit leg
- Elasticized cuffs
- Linen fabric
- Fits true to size
Style Number/Barcode: 06302-0640
Category Name: Summer Looks
Price: $12.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Like It Or Dot Puff Sleeve Crop Top
Like it or not, this polka dot crop top will surely be your fav! It features short puff sleeves, a sweetheart neckline, and a tie-front closure. The top is composed of a lightweight woven fabric that offers a relaxed fit with minimal stretch. Complete the look in the matching shorts.
Shop Matching Shorts: Like It Or Dot High Rise Shorts
Fit & Features
- Short puff sleeves
- Sweetheart neckline
- Tie-front closure
- Cropped hem
- Polka dot pattern
- Lightweight woven fabric
- Runs true to size
Style Number/Barcode: 06001-4103
Category Name: Summer Looks
Price: $6.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Like It Or Dot High Rise Shorts
Like it or not, these polka dot shorts will surely be your fav! It features a high-rise waist and a flowy silhouette. The shorts are composed of a lightweight woven fabric that offers a relaxed fit with minimal stretch. Complete the look in the matching top.
Shop Matching Top: Like It Or Dot Puff Sleeve Crop Top
Fit & Features
- High-rise waist
- Flowy silhouette
- Polka dot pattern
- Lightweight woven fabric
- Relaxed fit, minimal stretch
- Runs true to size
Style Number/Barcode: 06503-0961
Category Name: Summer Looks
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Beachside Brunch Swim Coverup Dress
Strut down the pier looking so fab in this maxi coverup dress featuring a sleeveless V-neckline, tank straps, and a form-fitting silhouette with a sultry front slit. The coverup dress is composed of an unlined semi-sheer knit fabric that offers a form-hugging fit. Perf for layering over your bikinis, complete the look in sandals.
Shop More Sweater Dresses: Sweater Dress Collection
Fit & Features
- Sleeveless V-neckline, tank straps
- Surplice accent
- Form-fitting silhouette
- Front slit
- Maxi-length hem
- Unlined, semi-sheer sweater-knit fabric, no stretch
- Runs true to size
Style Number/Barcode: 06005-1250
Category Name: Summer Looks
Price: $7.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance