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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Jess Off The Shoulder Dress
You're known for your moves—make 'em in our dynamite midnight blue satin Jess dress! She features an off-the-shoulder neckline, seamless sleeveless bodice with fold-over detail and back zip, and an A-line flared mini with pockets at either hip. Jess is made from a smooth, shiny material with moderate stretch.Model is 5’9” with a 32” bust, 24.5 waist, and 35” hips. She is wearing a size small.
Special Occasion products cannot be returned to any retail locations.
Style Number/Barcode: 05001-0002
Category Name: Night Out
Price: $29.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Club Crop Ring Front Top
Head out in high style when you don this retro-chic crop! Top hits below bust and features long, gathered sleeves and a deep V neck anchored by a large O-shaped ring with attached, extra-long wraparound waist tie. Top is made from a smooth jersey material with a touch of stretch.Style Number/Barcode: 06003-0273
Category Name: Night Out
Price: $12.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Little Black Envelope Clutch
This little black clutch is a staple to your wardrobe, featuring an envelope style snap closure. The exterior is composed of a faux textured leather material while the inside is lined with a knit material. Includes a dainty gold chain strap.Style Number/Barcode: 07203-1889
Category Name: Night Out
Price: $10.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Radiant In Rhinestones Mini Dress
Look beyond radiant in this simply stunning mini dress! It features a sleeveless bodice, spaghetti straps, a V neckline, an open back with a glimmering rhinestone bar accent, vertical seams that run down the bust, a high waist seam, a ruched side detail, and an asymmetrical wrap hem. The dress is composed of a crepe fabric that offers moderate stretch and a form hugging fit.
Model is 5'3" with a 32" bust, 22.5" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05103-3628
Category Name: Night Out
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Boldly Beautiful Bustier Bodysuit
Yes babe, you'll be boldly beautiful in this gorg bustier bodysuit! It features a sleeveless bodice, adjustable spaghetti straps, a bustier style top with padded cups with a nude lining, a square back with a zipper and hook and eye closure, and a thong bottom with snap button closures. The sheer mesh bodysuit features a pretty floral lace detail and offers minimal stretch.
Style Number/Barcode: 06003-9917
Category Name: Night Out
Price: $11.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Butterfly Rhinestone Ring Set
Come out of your cocoon with style! These flirty fluttering rings are an adorable addition to your girly look! Designed with an over-sized rhinestone butterfly, set comes with two rings that are able to stretch for adjustments in size.Style Number/Barcode: 07004-0022
Category Name: Night Out
Price: $7.97 $15.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Crisp And Classy Clutch
Show off a little class with a crisp new clutch. With a rectangular structure, a matching flap, and a snap closure. This clutch is easily a go-to. Clutch includes a smooth inner lining with a small zipper pocket as well as a detachable chain link strap. Material is a texted faux leather.
Style Number/Barcode: 07203-0019
Category Name: Night Out
Price: $12.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Set The Record Straight Pinstripe Midi Dress
It's a done deal. You'll be wanting to head straight to the party in this sultry midi!
Fits & Features
- V-Neckline
- Adjustable Shoulder Straps
- Zipper & Hook And Eye Closure At Back
- Fully Lined, Velvet Composition I Glitter Pinstripe Design Throughout
- Front Thigh High Slit
- Form-Hugging Fit I Moderate Stretch
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small
Style Number/Barcode: 05101-0236
Category Name: Night Out
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Live Forever Rhinestone Caged Heels
Let the party live forever! These sparkling heels are the center of attention no matter where you go! Designed with an almond shaped open toe, a tall block heel with a zipper closure at the back and a caged detailing down the center that is embellished with rhinestones!Style Number/Barcode: 07401-0342
Category Name: Night Out
Price: $24.97 $40.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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In The City Glitter Mini Dress
Take a night out on the town with a dress that catches the city lights!
Fits & Features
- V Neckline
- Long Sleeves
- Cinching At Center Front Bodice
- Form-Fitting, Mini Length Silhouette
- Knit Fabric Adorned With Glitter
- Curve Hugging Fit I Moderate Stretch
- Glitter May Transfer
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small
Style Number/Barcode: 05101-0002
Category Name: Night Out
Price: $27.00 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Stay Sweet Velvet Mini Dress
Stay sweet and stylish in this classic velvet mini dress!
Fits & Features
- Off Shoulder Neckline With Short Straps
- Faux Wrap Front V Neckline
- High Waist Seam
- Asymmetrical Short Hem
- Soft Velvet Composition
- Moderate Stretch
Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05101-8837
Category Name: Night Out
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Glitter Mama Mini Dress
The dress features a high crew neckline, and short cap sleeves. It is composed of a mesh material that is see through at the sleeves, sides, and back. Dress offers maximum stretch with a textured glitter overlay and includes a smooth inner lining. The stitching of the dress is unique and offers a low back with coverage for a sexy vibe that leaves more to the imagination. The hem hits above mid-thigh. Glitter may transfer.
Black: Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Rose Gold: Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small
Style Number/Barcode: 05103-0128
Category Name: Night Out
Price: $13.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Heavenly Sequins Off Shoulder Mini Dress
You'll be looking all types of angelic. Wow the crowd in this sequined mini!
Fits & Features
- Off Shoulder Sleeves
- Plunging Wire V Neckline With Padded Cups
- Square Back With Zipper & Hook And Eye Closure
- Mini Length Silhouette
- Mesh Knit With Scroll & Diamond Pattern Sequins Throughout
- Fully Lined
- Bodycon Fit I Ample Stretch
White: Model is 5'9" with a 34" bust, 24" waist and 35.5" hips. She is wearing a size small.
Mauve: Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small
Style Number/Barcode: 05101-0235
Category Name: Night Out
Price: $9.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Wanderlust Over The Knee Stiletto Boots
You are a wanderlust, and have a desire for adventure, and a long with that you love to look good on your endeavors! And these thigh high boots will take u there babe!
- Thigh high fit
- Adjustable lace up detail
- Almond toe
- Inner zipper closure
- Faux suede
Style Number/Barcode: 07402-0035
Category Name: Night Out
Price: $24.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Best Friend Diamond Quilted Clutch
She'll be by your side wherever you go—grab this clutch and get out there! Box-style purse has a structured body and features all-over diamond quilting with hardware including top fasten closure and detachable chain strap. Clutch is made from a faux leather material.
Style Number/Barcode: 07203-0045
Category Name: Night Out
Price: $11.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Must V Fate Glitter Mini Dress
It's written in the stars. You'll be glittering and glowing with the Must V Fate mini dress!
Fits & Features
- Plunging V Neckline
- Long Fitted Sleeves With Padded Shoulders
- Mini Length Silhouette
- Body-Hugging Fit
- Moderate Stretch
- Glitter Knit Fabric
Model is 5'9" with a 34" bust, 24" waist and 35.5" hips. She is wearing a size small.
Style Number/Barcode: 05101-0232
Category Name: Night Out
Price: $14.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Lovely Lace Off The Shoulder Mini Dress
Strut your stuff in this pretty little lace dress. It features an off the shoulder design, unlined long sleeves, and a mini-length silhouette. Crafted from scalloped lace fabric and lined with a soft rib knit, this dress offers a moderate stretch fit. Zipper not included.
Model is 5'7" with a 32" bust, 23" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 05101-0231
Category Name: Night Out
Price: $10.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Callin' The Shots Lace Blazer
You are calling the shots in this bossy blazer! Designed with a collared neckline, an open front with a hook and eye closure at the center, long sleeves, and a hem that hits passed the waist line. Blazer is composed of a floral lace material that offers a classy look with a little edge, a form fit, and moderate stretch.Style Number/Barcode: 06202-0040
Category Name: Night Out
Price: $12.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Bring Sexy Back Beaded Bodysuit
Bring sexy back in a bangin' bodysuit! Designed with a crew neckline, long sleeves and a thong snap closure bottom. Bodysuit is composed of a sheer mesh fabric that is form fitting and offers moderate stretch. Beaded and embellished with sequins the sweetheart forming accents give a beautiful detailed finish.
Model is 5'9" with a 32" bust, 24.5" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 06001-1714
Category Name: Night Out
Price: $16.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Rhinestone Mesh Cross-body Clutch
Sparkle Sparkle! We love things that shine! This clutch is designed with a structured body that is rectangular shaped, covered in mesh material and embellished with rhinestones! Clutch snaps open and has a satin inner lining and a detachable chain link cross-body strap.Style Number/Barcode: 07204-0036
Category Name: Night Out
Price: $14.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Satin Dreams Trench Duster
The satin saga continues with an absolutely stunning satin duster! Designed with long sleeves, a collared neckline, and a long hem that hits at the knees. Composed of a satin material that offers no stretch. Duster has pockets and button detailing at the shoulders and wrists.
Model is 5'9" with a 32" bust, 24.5" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 06204-0191
Category Name: Night Out
Price: $16.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Stripe A Pose Jumpsuit
The best part about jumpsuits is that they do all the work! This piece features a v neckline, a high waist seam above the hips, and a form fitting sleeveless bodice. Pants flare to a wide leg hem, and the back of the piece has a criss cross detail with a keyhole cut out located lower back. Composed of a pinstripe knit material with a smooth inner lining at the cup, this jumpsuit offers moderate stretch.Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06502-0070
Category Name: Night Out
Price: $13.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Boss Babe Crepe Longline Blazer
Command the boardroom like the boss you are in this crepe blazer! It features three-quarter length ruched sleeves, a flat collared neckline, and a longline design. Layer over high-rise bottoms and a chic blouse.
Fit & Features
- Flat collar, open front
- Three-quarter length ruched sleeves
- Longline design
- Side pockets
- Textured crepe fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06204-0200
Category Name: Night Out
Price: $17.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Hammered O-Ring Dusters
Add a modern twist to your everyday look! These dusters are oblong shaped and feature a double O design with a hammered finish.Style Number/Barcode: 07001-0163
Category Name: Night Out
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free