Night Out
Plans after dark call for outfits that know how to show up. This edit of going out outfits is built for rooftop bars, concerts, birthday celebrations, and spontaneous nights that start with one drink and end somewhere unexpected. Expect curve-hugging mini dresses, statement separates, and matching sets designed to mix, match, and move with you. Cowl necklines, strapless tops, and halter silhouettes bring just the right amount of edge, while sparkly crop tops and bustiers pair effortlessly with faux leather minis or relaxed cargo pants. Finish the look with a sleek moto jacket or bomber — because a good night out always deserves a great outfit.
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Going-Out Outfits for Every Fall & Winter Plan
Windsor’s Going-Out Outfits make getting ready feel effortless, whether the plan is dinner and drinks, a bar night with friends, a date, party, or night at the club. Find curve-hugging minis, statement separates, matching sets, denim, and sexy outfits with bold details that instantly turn up your look. From laid-back nights to full-glam entrances, these night-out outfits make it easy to dress for the vibe while creating a look that feels completely your own.
What Should I Wear for a Night Out?
Start with the mood and where you're headed. For dinner or date night, try a cowl-neck or halter top with embellished jeans or a denim skort for an elevated look that doesn't feel overdone. When drinks turn into dancing, strapless tops, plunging necklines, hardware details, and open-back silhouettes bring more after-dark energy. Explore going-out tops designed to mix, match, and move with you from the first stop to the last.
For an instant outfit, going-out dresses take the guesswork out of getting ready. Bodycon minis, curve-hugging silhouettes, bold prints, and romper dresses with flirty ruffle skirts give you one-and-done options that still make a statement.
Want the whole look with even less styling? Matching sets make getting ready easy, from sparkling coordinates that bring instant party energy to trending denim sets with vests for more laid-back plans. Wear the pieces together for effortless impact, then remix them with other going-out favorites. Discover more matching sets for going-out plans when you want an instantly coordinated look.
What Going-Out Outfits Are Trending in Fall 2026?
Fall going-out style mixes seasonal color and statement denim with silhouettes that still show some skin. Try embellished jeans with a backless top for drinks, a trending denim set for a harvest event, or an asymmetrical mini with boots for a night downtown. Jorts, boleros, bold prints, and unexpected separates also give you more ways to experiment with your look, especially when Halloween plans call for an outfit that can become part of a costume or make a statement all on its own.
For Friendsgiving dinner, pair a halter or cowl-neck top with statement denim for a look that feels dressed up without going full party glam. For bar nights or weekend hangs, balance standout style with an outfit that fits the setting. Get inspired by what to wear to a bar for outfit ideas that work for everything from casual drinks to a livelier night out.
What Should I Wear for a Winter Night Out?
For a winter night out, build your look with pieces that bring the heat while giving you more coverage as temperatures drop. Try a long-sleeve mini or bodycon dress with knee-high boots, or pair a statement top and embellished denim with a faux fur jacket for dinner, drinks, or a night downtown. Gloves and chic layering pieces add extra warmth while keeping the finished outfit polished.
For holiday parties and club nights, turn up the glam with sparkle, plunging or open-back details, sleek boots, and long-sleeve styles that balance the season with after-dark appeal. Heading into New Year’s Eve? Explore Fierce and Sexy Clubwear for bold looks made for celebrating long after midnight.
Find a Going-Out Look That Feels Like You
The best going-out look fits your plans without losing your personality. Keep things casual with denim and a statement top, make getting dressed easy with a matching set, or go all-out in a mini that puts the focus on you. Windsor’s Going-Out Outfits give you the pieces to mix, match, experiment, and create a look for every mood—from laid-back fall hangs to glamorous winter celebrations.
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Classic Staple Wide-Fit Block Heels
This chic pair of block heels are a classic staple you need in your wardrobe. They feature a comfortable wide-fit design with an open almond-shaped toe, a toe strap, an adjustable ankle strap with a buckle detail, and a sturdy block heel. The heels are composed of a faux leather material. Complete your formal look with a sleek envelope clutch.
Fit & Features
- Wide-fit design
- Open almond-shaped toe, toe strap
- Adjustable ankle strap, circular buckle
- Closed back
- Block heel
- Faux leather material, faux leather insole
- Runs true to size
Style Number/Barcode: 07401-3899
Category Name: Night Out
Price: $12.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Dressed Up In Sequins Midi Dress
Shimmer and shine in this sequin midi dress for the next party or night out! The dress features a sleeveless scoop neck, mesh spaghetti straps that lace up along the open-back design, a bodycon fit, and a side slit hem. Complete your radiant look with a chic ring set and heels!
Fit & Features
- Sleeveless scoop neck
- Mesh spaghetti straps
- Lace-up open-back design
- Hidden back zipper and hook-eye closure
- Bodycon, midi hem with side slit
- Sequin fabric, knit lining, moderate stretch
- Fits true to size
Style Number/Barcode: 05101-2131
Category Name: Night Out
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Boho Daze Long Sleeve Tie-Front Lace Top
Create a dreamy bohemian look for festival season with this long sleeve tie-front lace top! The airy sheer lace fabric will give your 'fit that effortlessly chic vibe. The top features a V-neckline, long fitted sleeves for coverage, and a trendy tie-front design leading to a center-front slit with a subtle flowy fit. Style with flare pants and strappy sandals.
Fit & Features
- Sheer lace fabric, lettuce edge hem
- Minimal stretch
- V-neckline
- Long fitted sleeves
- Tie-front design
- Center-front slit
- Runs true to size
Style Number/Barcode: 06202-0442
Category Name: Night Out
Price: $12.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Snake Skin Tight Lace-Up Faux Leather Corset Top
Keep it skin tight in this saucy snake print faux leather corset top for a cool-girl vibe out on the town! Made from a sleek faux leather fabric with a snake print, this strapless corset boasts a sweetheart neckline, flexible boning for a snatched look, and bungee strap lace-up trims that add sultriness to the cropped silhouette. Complete the look in sleek faux leather leggings and heels!
Fit & Features
- Faux leather fabric lined with sewn-in knit lining
- Snake print
- Flexible boning
- Back zipper and hook-eye closure
- Lace-up trims
- Cropped hem
- Runs true to size
Style Number/Barcode: 06003-2444
Category Name: Night Out
Price: $6.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sultry Perfection Mesh Cropped Bustier Top
This airy mesh cropped bustier top is simply sultry perfection! Designed with a stretchy sheer mesh fabric with a knit lining, this top features sexy details for an iconic night-out look. The sleeveless bodice is shaped with a sweetheart neckline with a built-in padded bust and ruching, a bustier design with flexible boning inserts for structure, and adjustable spaghetti straps for a customized fit. The angled cropped hem will create a snatched silhouette. Style this bustier top with a mini skirt and heels.
Fit & Features
- Sheer mesh fabric with knit lining, plenty of stretch
- Sleeveless sweetheart neckline, padded bust, ruching
- Bustier bodice, flexible boning
- Adjustable spaghetti straps
- Angled cropped hem
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06001-5050
Category Name: Night Out
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Irreplaceable Cropped Graphic Tee
Know your worth and style up this adorable graphic tee featuring a crew neckline, short sleeves, a front script reading, "Irreplaceable" in bolded lettering, and a fitted cropped hem. Pair with a mini skirt and knee-high boots!
Fit & Features
- Cotton-blend fabric, moderate stretch
- Crew neckline
- Short sleeves
- Script reading, "Irreplaceable"
- Fitted cropped hem
- Runs true to size
Style Number/Barcode: 06002-1993
Category Name: Night Out
Price: $6.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Dreamy Mix Long Sleeve Ruffle Lace A-Line Dress
A dreamy mix of sophistication and sultry, this lace A-line mini dress is perfect for cocktail hour! Featuring sheer fitted sleeves with delicate ruffled cuffs, a plunging V-neckline adorned with femme ruffle trim and satin ties, and a flirty A-line silhouette with a playful ruffled hem. Complete the look in stiletto heels and a clutch!
Fit & Features
- Lace fabric lined with stretchy knit
- Sheer fitted long sleeves, ruffle cuffs
- Plunge V-neckline, ruffle trim, satin ties
- A-Line silhouette
- Ruffled hem
- Runs true to size
Style Number/Barcode: 05101-3368
Category Name: Night Out
Price: $9.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Classic Perfection Block Heels
These sleek faux leather block heels are classic perfection! They feature an open almond-shaped toe with a strap, a thin ankle strap, a back zipper closure, and a sturdy block heel. Style with a crossbody bag.
Fit & Features
- Open almond-shaped toe
- Toe strap
- Thin ankle strap
- Back zipper closure
- Block heel
- Faux leather material
- Runs true to size
Style Number/Barcode: 07401-4150
Category Name: Night Out
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Party Town V-Neck Cutout Mini Dress
This mini dress is ready to party all over town! The short dress features a sleeveless V-neckline with a cowl draping, adjustable spaghetti straps, a cutout waist with criss-cross straps, and a bodycon silhouette on stretchy lined knit fabric. Style this mini party dress with a sparkly bracelet and heels!
Fit & Features
- Sleeveless V-neck, cowl draping
- Adjustable spaghetti straps
- Cutout waist, criss-cross straps
- Bodycon silhouette
- Mini-length hem
- Lined knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05103-4710
Category Name: Night Out
Price: $6.97 $37.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Shake It Off Sequin Crop Top
Shake off what the haters have to say and slay in sassy snake skin! This crop top features a sleeveless bodice, a scoop neckline with corded straps, a cropped hemline and an all over snakeskin print that is adorned with gleaming sequins to bring the drama! Crop top is composed of a smooth knit fabric that features taupe, gray and brown hues. Top offers a relaxed fit with a moderate stretch. Includes a smooth knit lining. Don't forget to pick up the matching skirt to complete your confident look!Model is 5'7" with a 34" bust, 24" waist and 36 hips. She is wearing a size small
Style Number/Barcode: 06001-0422
Category Name: Night Out
Price: $6.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Drape And Shimmer Cowl Neck Tank Top
Drape yourself in a luxurious shimmering top! This elegant tank is designed with a cowl neck draped neckline, spaghetti straps, and a mid length hemline. Top has a slinky fit, and is composed of a shimmering knit material that offers moderate stretch.
Model is 5'6.5" with a 32" bust, 23.5" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 06001-1939
Category Name: Night Out
Price: $4.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Crushin' On U Rhinestone Platform Heels
Girl we are crushin' on you in those eye catching sparkling heels! Style with flared pants, or a jumpsuit for vintage disco vibez-
- Open almond toe
- Platform sole
- Tall block heel
- Single band over the toe
- Rhinestone detailing
- Ankle strap with adjustable pin buckle closure
- Faux nubuck
Style Number/Barcode: 07401-0702
Category Name: Night Out
Price: $12.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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She's Irresistible Faux Leather A-Line Mini Skirt
A faux leather mini skirt like this will make you simply irresistible! This high-rise skirt flaunts side button details for an edgy vibe and a flirty a-line silhouette perfect for pairing with heels or boots.
Fit & Features
- Sleek faux leather fabric
- High-rise waist
- Side snap-button and zipper closures
- A-line silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 06401-0736
Category Name: Night Out
Price: $16.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sleeveless Sweetheart Neck Corset Lace Jumpsuit
Keep it chic in a lace jumpsuit. Go from the office to happy hour in a statement jumpsuit. This jumpsuit features a sleeveless sweetheart neckline, a corset-like bodice and adjustable spaghetti straps that lead to a partially open back. The lined bodice features a two-tone lace fabric and piping detailing. The relaxed fit bodice leads to a pair of straight-leg pants with a flared hem.
Fit & Features
- Sleeveless sweetheart neckline
- Corset-like bodice with piping accents
- Adjustable spaghetti straps
- Partially open back
- Straight leg pants with a flared hem
- Form hugging fit
Model is 5'6" with 31" bust, 26" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06502-0381
Category Name: Night Out
Price: $16.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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High Waist Luxe Velvet Pants
Bring the luxe in high waist pants that are perfect for dressing up in! The pants feature a high rise waist, side pockets, and a straight leg fit. The pants are composed of a lined velvet fabric that offers a relaxed fit with a moderate stretch. Complete look with a crop top.
Fit & Features
- Elastic high rise waist
- Slant pockets
- Straight leg fit
- Lined velvet fabric
- Relaxed fit, moderate stretch
Style Number/Barcode: 06502-0413
Category Name: Night Out
Price: $6.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Bring The Heat Sheer Mesh Embellished Crop Top
This sheer mesh crop top will totally bring the heat to your fab 'fit! It features long fitted sleeves, a cropped, form-fitting style, and front heat stone embellishement with a sweetheart neckline design. Pair this top with a faux leather mini skirt for your next night out.
Fit & Features
- Crew neckline
- Long fitted sleeves
- Cropped, form-hugging fit
- Sheer mesh fabric with a partial front knit lining
- Plenty of stretch
- Front heat stone embellishment
Style Number/Barcode: 06001-2874
Category Name: Night Out
Price: $11.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Glam It Up Lace Lattice Back Bodysuit
Glam it up in a lace bodysuit that brings a sultry vibe to your look! The bodysuit features a mock neck, an unlined bodice, a floral lace print, a sexy lattice back, and a form-hugging fit. Complete look with a high waist skirt.
Fit & Features
- Mock neck
- Unlined bodice
- Floral lace print
- Long sleeves
- Lattice back
- Form hugging fit
- Bralette/Cami pictured on model is not included
Style Number/Barcode: 06001-3023
Category Name: Night Out
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Edgy Glam Lug Sole Ankle Booties
Bring that edgy glamour with booties that bring the attitude to your look! The booties feature an around the ankle fit, an inner zipper closure, an almond toe, a lug sole, and a low block heel. The booties are composed of a faux leather material. Complete look with a graphic tee and cargo pants.
Fit & Features
- Around the ankle fit
- Inner zipper closure
- Almond toe
- Lug sole
- Low block heel
- Faux leather material
- Runs true to size
Style Number/Barcode: 07403-1437
Category Name: Night Out
Price: $12.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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She's A Stunner Faux Leather Crossbody
Create a head-turning statement in a crossbody that brings the chic factor to your look! The crossbody features a large rounded body with scrunched detailing, chunky chain link handles and composed of a faux leather material. Complete look with a long sleeve mini dress and mules.
Fit & Features
- Large rounded body
- Scrunched detailing
- Chunky chain link handles
- Detachable shoulder strap
- Faux leather material
Style Number/Barcode: 07203-0471
Category Name: Night Out
Price: $17.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Dreamy And Chic Satin Mini Skirt
Get a luxe look in this dreamy and chic satin skirt! It features a high-rise waist, ruched detailing with an adjustable drawstring leading to a side slit, and a mini-length, curve-hugging silhouette. Style this skirt with the matching crop top for your next girl's night out.
Shop Matching Top: Dreamy And Chic Satin Crop Top
Fit & Features
- High-rise waist
- Back zipper and hook and eye closure
- Ruched detailing, adjustable drawstring
- Side slit
- Short, form-fitting silhouette
- Smooth satin fabric, knit lining, minimal stretch
- Runs true to size
Style Number/Barcode: 06401-0350
Category Name: Night Out
Price: $6.97 $27.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Step Out Trendy Stiletto Sock Booties
Step out in style in these trendy stiletto sock booties. They feature a dramatic pointed toe, faux suede material at the front, an above-the-ankle ribbed knit sock design, and a sleek faux suede stiletto heel. Pair these booties with a mini skirt and cropped sweater.
Fit & Features
- Pointed toe
- Faux suede material at the front
- Above-the-ankle ribbed knit sock design
- Faux suede stiletto heel
- Runs true to size
Style Number/Barcode: 07403-1448
Category Name: Night Out
Price: $8.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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What's The Ruche Mesh Mini Dress
The latest dish everyone will be talking about is you in this mesh mini dress! Hit the town with the girls in this spicy little number featuring a sleeveless, square neck, adjustable spaghetti straps, and all-over ruched seams that complement the bodycon silhouette. Complete the look in sleek hoop earrings.
Fit & Features
- Sleeveless, square neck, adjustable spaghetti straps
- All-over ruched seams
- Bodycon silhouette
- Mini-length hem
- Mesh-lined fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05103-4444
Category Name: Night Out
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Metallic Moves Block Heels
Make stylish moves in these fabulous metallic block heels. They feature an open almond-shaped toe, a toe strap with mini rhinestone embellishments, a thin adjustable ankle strap, a block heel, and an all-over chic chrome sheen. Style with a sleek satin dress and sparkly earrings.
Fit & Features
- Open almond-shaped toe
- Toe strap, mini rhinestone embellishments
- Thin adjustable ankle strap, buckle detail
- Closed back
- Block heel
- Chrome sheen
- Faux leather material, faux leather insole
- Runs true to size
Style Number/Barcode: 07401-4044
Category Name: Night Out
Price: $22.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Alluring Trendsetter Halter Midi Dress
Show off your alluring trendy style in this sleek curve-hugging midi dress! It features a cross-front halter neckline with tie-back straps, a cold-shoulder design with long fitted sleeves, and a midi-length asymmetric hem creating a chic high side slit. The smooth knit fabric includes a full lining. Complete the look with your fave mules.
Fit & Features
- Cross-front halter neckline, tie-back straps
- Cold-shoulder design
- Long fitted sleeves
- Midi-length asymmetric hem, high side slit
- Form-hugging silhouette
- Knit fabric, full lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4904
Category Name: Night Out
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale