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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Total It Girl Belted Trench
Be a total it girl with this chic and sophisticated belted trench! It features long fitted sleeves, a front flowy lapel collar, an elastic banded back, and a tie front belt. The jacket is composed of a lightweight woven fabric that offers a relaxed fit with no stretch.Style Number/Barcode: 06204-0203
Category Name: Night Out
Price: $13.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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High Waist Satin Leggings
Sleek satin gives these high waist leggings their chic edge. They feature an elastic banded waist paired with slim fitting pant legs. The satin-like fabric offers plenty of stretch.
Model is 5'7" with a 32" bust, 23" waist and 35.5" hips. She is wearing a size small.
Style Number/Barcode: 06502-0201
Category Name: Night Out
Price: $6.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Ingrid Lurex X Front Dress
Special Occasion
Show off those shoulders and sparkle all night long in our elegant Ingrid dress! She has a body con construction and features a dramatic, draped X-front neckline, a tank-style back with zip closure, and a seamed, midi-length skirt with a small front slit.
Special Occasion products cannot be returned to any retail locations.
Style Number/Barcode: 05001-0317
Category Name: Night Out
Price: $19.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Glamorous Girl Mini Skirt
Shop Matching Top: Glamorous Girl Crop Top
You're a total glam girl at heart, so this sequin adorned mini skirt is a perfect match. It features a high rise waist, a back zipper and hook and eye closure, and a short, form hugging fit. The mesh fabric includes a front and back knit lining and offers moderate stretch. Complete your glitzy look with the matching crop top!
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06401-0053
Category Name: Night Out
Price: $13.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Too Busy Stiletto Heels
When you're just too busy to give af about anything but ur heel game!
- Open almond shaped toe
- Single band
- Velcro ankle closure
- Faux suede
- Stiletto heel
Style Number/Barcode: 07401-1171
Category Name: Night Out
Price: $12.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Marvelous Mesh Mini Dress
Marvel them all with this pretty mini dress! It features a partially unlined bodice, a mock neck, unlined mesh long sleeves with fringed cuffs , a sweetheart bust lining with padded cups and a fringe lace detailed waist that leads to a mini length silhouette. Dress is composed of combination mesh, lace and crepe fabric that offers a form hugging fit with a moderate stretch. Includes an exposed back zipper.
Style Number/Barcode: 05103-3618
Category Name: Night Out
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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High Waist Floral Ruched Knit Mini Skirt
Impress this season in a floral skirt. Dress up your basic tops with a floral mini skirt that features a flattering high rise waist, ruched side seams with drawstring ties, and an all-over floral print. The skirt is composed of a smooth knit fabric that enhances curves with a moderate stretch. Complete your outfit with strappy heels and a dainty necklace for a daytime look.
Fit & Features
- High rise waist
- Ruched side seam with drawstring ties
- Floral print
- Mini length silhouette
- Smooth knit fabric
- Form hugging fit, moderate stretch
Model is 5'4" with 33" bust, 24.5" waist and 39" hips. She is wearing a size small.
Style Number/Barcode: 06501-0262
Category Name: Night Out
Price: $8.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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So Rare Pearl Embellished Crop Top
Radiate your rare beauty in a pearl top that brings the luxe! The top features a scoop neckline, a faux-pearl embellishment throughout, and a cropped hem. Create a dazzling night out look when styled with dark wash denim jeans.
Fit & Features
- Sleeveless scoop neckline
- Spaghetti straps
- Faux pearl embellishment
- Cropped hem
Style Number/Barcode: 06003-0673
Category Name: Night Out
Price: $16.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sassy Shine Glitter Lurex Tie Waist Top
This shimmering top is what you need to illuminate your date night. The top features a cowl neckline, cap sleeves, a tie waist hem, and composed of a lurex glitter knit fabric. Complete your look with a faux leather mini skirt.
Fit & Features
- Cowl neckline
- Cap sleeves
- Tie waist hem
- Glitter lurex fabric
- Form hugging fit
- Moderate stretch
The saturation of glitter varies. Glitter may transfer.
Style Number/Barcode: 06001-2933
Category Name: Night Out
Price: $10.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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So Chic Faux Leather Heels
Bring it back to basics in these heels that go with all your favorite casual and formal looks! The heels feature a closed-back, an open square toe with a single strap over the toe, and a narrow block heel. Complete look with a ribbed bodycon dress.
Fit & Features
- Closed-back
- Open square toe with a single strap over the toe
- Adjustable ankle strap
- Narrow block heel
- Faux leather material
Style Number/Barcode: 07401-2531
Category Name: Night Out
Price: $7.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Being Chic One-Shoulder Cutout Wide-Leg Jumpsuit
Strut into a dinner party in this chic wide-leg jumpsuit and be prepared to receive many compliments! Pair with a clutch and heels for a fab look.
Fit & Features
- Stretchy knit fabric
- One-shoulder neckline
- One shoulder strap, metal accent, cutout
- Wide-leg silhouette
- Runs true to size
Style Number/Barcode: 06502-000012
Category Name: Night Out
Price: $6.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Luxe Life Chainmail Crop Top
Live it up in luxe with a crop top that brings the shine. It features a trendy halter neck, a halter top chain strap, and a cropped hem with fringe. Whether you are going out for drinks, or you are heading out to a party, style this piece with faux leather bottoms.
Fit & Features
- Halter neck
- Halter neck chain strap
- Cropped hem
- Fringe
- Open back
- Chainmail
- Runs true to size
Style Number/Barcode: 06003-0999
Category Name: Night Out
Price: $6.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Bring The Sparkle Sequin Mini Dress
Bring the sparkle to your night-out look with this stunning mini dress. It features a sleeveless deep V-neckline, adjustable spaghetti straps that lead to a cross-back design, a short, curve-hugging silhouette, and embroidered sequins in a chic scroll pattern. Complete the outfit with clear heels.
Fit & Features
- Sleeveless deep wired V-neckline
- Padded cups
- Adjustable spaghetti straps, cross-back design
- Back zipper closure
- Mini-length, form-hugging fit
- Embroidered sequins in a scroll pattern
- Runs true to size
Style Number/Barcode: 05101-0981
Category Name: Night Out
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Be The Vibe Strapless Crop Top
Everyone will want to match your vibe in this sassy crop top! The flattering strapless design showcases your shoulders beautifully while the cropped silhouette accentuates your figure.
Fit & Features
- Burnout velvet pattern, mesh fabric, bust knit lining
- Strapless neckline
- Pointed crop top
- Runs true to size
Style Number/Barcode: 06003-000051
Category Name: Night Out
Price: $6.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Encircled In Glam Rhinestone Belt
Embrace your glam side with a rhinestone belt! The belt features a multi-row rhinestone band and an oval-shaped buckle. Complete look with an LBD and heels.
Fit & Features
- Multi-row design
- Oval-shaped buckle
- Rhinestones
Style Number/Barcode: 07301-0342
Category Name: Night Out
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Luxe Lace-Up Over-The-Knee Boots
Get a luxe look this season with these chic faux suede over-the-knee boots. They feature a closed pointed toe, an on-trend lace-up front design, an inner zipper closure, and a block heel. Style these boots with a plaid skirt and a cropped sweater.
Fit & Features
- Over-the-knee fit
- Closed pointed toe
- Lace-up front
- Partial inner zipper closure
- Block heel
- Faux microsuede material
- Runs true to size
Style Number/Barcode: 07402-0764
Category Name: Night Out
Price: $17.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Feeling Cool Pleated Faux Leather Mini Skort
Feel cool and cute in this faux leather mini skort out at a concert or party! The high-rise waist and pleated silhouette create a flattering fit while the mini-length hem adds a touch of sass. Plus, the stretchy knit shorts lining ensures comfort all day long. Complete the look in a crop tee.
Fit & Features
- Faux leather fabric, stretchy knit shorts lining
- High-rise waist
- Back zipper closure
- Pleated silhouette
- Mini-length hem
- Skort in size small has a 10.5" front rise with a 1.5" inseam
- Runs true to size
Style Number/Barcode: 06503-1159
Category Name: Night Out
Price: $13.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Simply Elevated Tie-Front Trench
Layer on this chic trench for a simply elevated look. It features a lapel collar, long sleeves, a tie-front waist to stylishly cinch, and a short, relaxed fit. Layer this trench over a basic bodysuit and your favorite pair of denim.
Fit & Features
- Lapel collar
- Long sleeves
- Tie-front waist
- Side pockets
- Short, relaxed fit
- Lightweight woven fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06204-1367
Category Name: Night Out
Price: $14.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Party Time Glitter Mesh Mini Dress
This glitter mini dress will inspire your next look for a party! It features sheer long sleeves, a square neck, and a bodycon silhouette. Style with strappy block heels to complete the look.
Fit & Features
- Sheer long sleeves
- Square neck
- Bodycon silhouette
- Mini-length hem
- Glitter mesh fabric, partial knit lining
- Moderate stretch
- Fits true to size
Style Number/Barcode: 05101-1943
Category Name: Night Out
Price: $19.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Love So Mesh Off-The-Shoulder Crop Top
The perfect mesh crop top for date nights, parties, or just feeling cute! Elevate your favorite bottoms with this sweet and sassy crop top featuring an off-the-shoulder neckline, sheer peasant long sleeves, a ruched and padded bust, and a fitted crop hem. Complete the look in a fitted midi skirt and heels.
Fit & Features
- Off-the-shoulder, sweetheart neckline
- Sheer peasant long sleeves
- Ruched and padded bust
- Cropped hem
- Lined mesh fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06001-4958
Category Name: Night Out
Price: $17.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Dreamy And Divine Lace Mini Skirt
Envoke a dreamy and divine allure in this lace mini skirt made to be seen on you! It features a flattering high-rise waist and bodycon silhouette with a lace trim mini-length hem for added charm. Complete the look with the matching top for a dressy night out!
Shop Matching Top: Dreamy And Divine Lace Long Sleeve Bustier
Fit & Features
- High-rise waist
- Bodycon silhouette
- Lace trim mini-length hem
- Lace fabric, sewn-in nude knit lining
- Moderate stretch
- Runs true to size
Style Number/Barcode: 06501-0954
Category Name: Night Out
Price: $5.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Pearl-Fect Pick Sweater Maxi Dress
Forever a perfect pick for your next chic soiree! This sweater maxi dress features long fitted sleeves, a plunge V-neckline, a center front faux pearl button-down along the bodycon silhouette, and a slit accent. The ribbed knit fabric offers a moderate stretch. Complete the look with pointed-toe booties.
Fit & Features
- Sweater ribbed knit fabric, moderate stretch
- Long fitted sleeves
- Plunge V-neckline
- Center front faux pearl button-down
- Bodycon fit
- Front slit
- Runs true to size
Style Number/Barcode: 06005-1525
Category Name: Night Out
Price: $6.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Show Stopper Strapless Lace Beaded Corset Top
Steal the show and look amazing in this strapless corset top paired with your favorite bottoms for a saucy night on the town! Featuring a strapless neckline and hidden front hook and eye fasteners, this top is so chic. The flexible boning provides a flattering silhouette, while the lace-up back adds a touch of romance. The lace-beaded embellished woven fabric is the perfect finishing touch. Complete the look in high-rise denim jeans and stilettos!
Fit & Features
- Lace beaded embellished woven fabric, lined, no stretch
- Strapless neckline
- Hidden front hook and eye fasteners
- Lace-up back
- Flexible boning
- Cropped length
- Runs true to size
Style Number/Barcode: 06003-2415
Category Name: Night Out
Price: $6.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Going Everywhere Belted Faux Suede Skort
Take this faux suede skort everywhere you go for total vibes! The high-rise folded belted waist adds a chic touch while providing a flattering fit. With a form-hugging silhouette and built-in shorts lining, you can confidently go anywhere and do anything in style. Complete the look in a short sleeve bodysuit and sandals.
Fit & Features
- Faux suede fabric, minimal stretch
- High-rise waist
- Form-hugging silhouette
- Shorts lining
- Runs true to size
Style Number/Barcode: 06403-0398
Category Name: Night Out
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free